0.4.4

Note: `--remote-host` must still be set, but it can be an 'alias' represented by the 'Host' value in the ssh config.

.forgejo/workflows/build-deb.yml

@@ -21,6 +21,7 @@ jobs:
           python3-poetry-core \
           python3-yaml \
           python3-paramiko \
+          python3-jsonschema \
           rsync \
           ca-certificates
 

.forgejo/workflows/ci.yml

@@ -15,7 +15,7 @@ jobs:
         run: |
           apt-get update
           DEBIAN_FRONTEND=noninteractive apt-get install -y --no-install-recommends \
-            ansible ansible-lint python3-venv pipx systemctl python3-apt
+            ansible ansible-lint python3-venv pipx systemctl python3-apt jq python3-jsonschema
 
       - name: Install Poetry
         run: |

CHANGELOG.md

@@ -1,3 +1,53 @@
+# 0.4.4
+
+ * Update cryptography dependency
+ * Add capability to handle passphrases on encrypted SSH private keys. Prompting can be forced with `--ask-key-passphrase` or automated (e.g for CI) with `--ssh-key-passphrase env SOMEVAR`
+
+# 0.4.3
+
+ * Add support for AddressFamily and ConnectTimeout in the .ssh/config when using `--remote-ssh-config`.
+ * Update dependencies
+
+# 0.4.2
+
+ * Support `--remote-ssh-config [path-to-ssh-config]` as an argument in case extra params are required beyond `--remote-port` or `--remote-user`. Note: `--remote-host` must still be set, but it can be an 'alias' represented by the 'Host' value in the ssh config.
+
+# 0.4.1
+
+ * Add interactive output when 'enroll diff --enforce' is invoking Ansible.
+
+# 0.4.0
+
+ * Introduce `enroll validate` - a tool to validate a harvest against the state schema, or check for missing or orphaned obsolete artifacts in a harvest.
+ * Attempt to generate Jinja2 templates of systemd unit files and Postfix main.cf (now that JinjaTurtle supports it)
+ * Update pynacl dependency to resolve CVE-2025-69277
+ * Add `--exclude-path` to `enroll diff` command, so that you can ignore certain churn from the diff (stuff you still wanted to harvest as a baseline but don't care if it changes day to day)
+ * Add `--ignore-package-versions` to `enroll diff` command, to optionally ignore package upgrades (e.g due to patching) from the diff.
+ * Add tags to the playbook for each role, to allow easier targeting of specific roles during play later.
+ * Add `--enforce` mode to `enroll diff`. If there is diff detected between the two harvests, and it can enforce restoring the state from the older harvest, it will manifest the state and apply it with ansible. Only the specific roles that had diffed will be applied (via the new tags capability)
+
+# 0.3.0
+
+ * Introduce `enroll explain` - a tool to analyze and explain what's in (or not in) a harvest and why.
+ * Centralise the cron and logrotate stuff into their respective roles, we had a bit of duplication between roles based on harvest discovery.
+ * Capture other files in the user's home directory such as `.bashrc`, `.bash_aliases`, `.profile`, if these files differ from the `/etc/skel` defaults
+ * Ignore files that end with a tilde or - (probably backup files generated by editors or shadow file changes)
+ * Manage certain symlinks e.g for apache2/nginx sites-enabled and so on
+
+# 0.2.3
+
+ * Introduce --ask-become-pass or -K to support password-required sudo on remote hosts, just like Ansible. It will also fall back to this prompt if a password is required but the arg wasn't passed in.
+
+# 0.2.2
+
+ * Fix stat() of parent directory so that we set directory perms correct on --include paths.
+ * Set pty for remote calls when sudo is required, to help systems with limits on sudo without pty
+
+# 0.2.1
+
+ * Don't accidentally add `extra_paths` role to `usr_local_custom` list, resulting in `extra_paths` appearing twice in manifested playbook
+ * Ensure directories in the tree of anything included with --include are defined in the state and manifest so we make dirs before we try to create files
+
 # 0.2.0
 
  * Add version CLI arg
@@ -16,8 +66,8 @@
 # 0.1.5
 
  * Consolidate logrotate and cron files into their main service/package roles if they exist.
- * Standardise on MAX_FILES_CAP in one place
- * Manage apt stuff in its own role, not in etc_custom
+ * Standardise on `MAX_FILES_CAP` in one place
+ * Manage apt stuff in its own role, not in `etc_custom`
 
 # 0.1.4
 

CONTRIBUTORS.md

@@ -0,0 +1,5 @@
+## Contributors
+
+mig5 would like to thank the following people for their contributions to Enroll.
+
+ * [slhck](https://slhck.info/)

Dockerfile.debbuild

@@ -26,6 +26,7 @@ RUN set -eux; \
       python3-poetry-core \
       python3-yaml \
       python3-paramiko \
+      python3-jsonschema \
       rsync \
       ca-certificates \
     ; \

Dockerfile.rpmbuild

@@ -1,5 +1,6 @@
 # syntax=docker/dockerfile:1
-FROM fedora:42
+ARG BASE_IMAGE=fedora:42
+FROM ${BASE_IMAGE}
 
 RUN set -eux; \
     dnf -y update; \
@@ -21,6 +22,7 @@ RUN set -eux; \
         python3-rpm-macros \
         python3-yaml \
         python3-paramiko \
+        python3-jsonschema \
         openssl-devel \
         python3-poetry-core ; \
         dnf -y clean all
@@ -33,24 +35,8 @@ set -euo pipefail
 SRC="${SRC:-/src}"
 WORKROOT="${WORKROOT:-/work}"
 OUT="${OUT:-/out}"
-DEPS_DIR="${DEPS_DIR:-/deps}"
-
-# Install jinjaturtle from local rpm
-# Filter out .src.rpm and debug* subpackages if present.
-if [ -d "${DEPS_DIR}" ] && compgen -G "${DEPS_DIR}/*.rpm" > /dev/null; then
-  mapfile -t rpms < <(ls -1 "${DEPS_DIR}"/*.rpm | grep -vE '(\.src\.rpm$|-(debuginfo|debugsource)-)')
-  if [ "${#rpms[@]}" -gt 0 ]; then
-    echo "Installing dependency RPMs from ${DEPS_DIR}:"
-    printf '  - %s\n' "${rpms[@]}"
-    dnf -y install "${rpms[@]}"
-    dnf -y clean all
-  else
-    echo "NOTE: Only src/debug RPMs found in ${DEPS_DIR}; nothing installed." >&2
-  fi
-else
-  echo "NOTE: No RPMs found in ${DEPS_DIR}. If the build fails with missing python3dist(jinjaturtle)," >&2
-  echo "      mount your jinjaturtle RPM directory as -v <dir>:/deps" >&2
-fi
+VERSION_ID="$(grep VERSION_ID /etc/os-release | cut -d= -f2)"
+echo "Version ID is ${VERSION_ID}"
 
 mkdir -p "${WORKROOT}" "${OUT}"
 WORK="${WORKROOT}/src"

README.md

@@ -11,8 +11,9 @@
 - Captures config that has **changed from packaged defaults** where possible (e.g dpkg conffile hashes + package md5sums when available).
 - Also captures **service-relevant custom/unowned files** under `/etc/<service>/...` (e.g. drop-in config includes).
 - Defensively excludes likely secrets (path denylist + content sniff + size caps).
-- Captures non-system users and their SSH public keys.
+- Captures non-system users and their SSH public keys and any .bashrc or .bash_aliases or .profile files that deviate from the skel defaults.
 - Captures miscellaneous `/etc` files it can't attribute to a package and installs them in an `etc_custom` role.
+- Captures symlinks in common applications that rely on them, e.g apache2/nginx 'sites-enabled'
 - Ditto for /usr/local/bin (for non-binary files) and /usr/local/etc
 - Avoids trying to start systemd services that were detected as inactive during harvest.
 
@@ -73,7 +74,7 @@ Harvest state about a host and write a harvest bundle.
 
 **Common flags**
 - Remote harvesting:
-  - `--remote-host`, `--remote-user`, `--remote-port`
+  - `--remote-host`, `--remote-user`, `--remote-port`, `--remote-ssh-config`
   - `--no-sudo` (if you don't want/need sudo)
 - Sensitive-data behaviour:
   - default: tries to avoid likely secrets
@@ -88,6 +89,27 @@ Harvest state about a host and write a harvest bundle.
     - glob (default): supports `*` and `**` (prefix with `glob:` to force)
     - regex: prefix with `re:` or `regex:`
   - Precedence: excludes win over includes.
+  * Using remote mode and auth requires secrets?
+    * sudo password:
+      * `--ask-become-pass` (or `-K`) prompts for the sudo password.
+      * If you forget, and remote sudo requires a password, Enroll will still fall back to prompting in interactive mode (slightly slower due to retry).
+    * SSH private-key passphrase:
+      * `--ask-key-passphrase` prompts for the SSH key passphrase.
+      * `--ssh-key-passphrase-env ENV_VAR` reads the SSH key passphrase from an environment variable (useful for CI/non-interactive runs).
+      * If neither is provided, and Enroll detects an encrypted key in an interactive session, it will still fall back to prompting on-demand.
+      * In non-interactive sessions, pass `--ask-key-passphrase` or `--ssh-key-passphrase-env ENV_VAR` when using encrypted private keys.
+    * Note: `--ask-key-passphrase` and `--ssh-key-passphrase-env` are mutually exclusive.
+
+Examples (encrypted SSH key)
+
+```bash
+# Interactive
+enroll harvest --remote-host myhost.example.com --remote-user myuser --ask-key-passphrase --out /tmp/enroll-harvest
+
+# Non-interactive / CI
+export ENROLL_SSH_KEY_PASSPHRASE='correct horse battery staple'
+enroll single-shot --remote-host myhost.example.com --remote-user myuser --ssh-key-passphrase-env ENROLL_SSH_KEY_PASSPHRASE --harvest /tmp/enroll-harvest --out /tmp/enroll-ansible --fqdn myhost.example.com
+```
 
 ---
 
@@ -105,6 +127,17 @@ Generate Ansible output from an existing harvest bundle.
 **Common flags**
 - `--fqdn <host>`: enables **multi-site** output style
 
+**Role tags**
+Generated playbooks tag each role so you can target just the parts you need:
+
+- Tag format: `role_<role_name>` (e.g. `role_services`, `role_users`)
+- Fallback/safe tag: `role_other`
+
+Example:
+```bash
+ansible-playbook -i "localhost," -c local /tmp/enroll-ansible/playbook.yml --tags role_services,role_users
+```
+
 ---
 
 ### `enroll single-shot`
@@ -128,6 +161,26 @@ Compare two harvest bundles and report what changed.
 **Inputs**
 - `--old <harvest>` and `--new <harvest>` (directories or `state.json` paths)
 - `--sops` when comparing SOPS-encrypted harvest bundles
+- `--exclude-path <PATTERN>` (repeatable) to ignore file/dir drift under matching paths (same pattern syntax as harvest)
+- `--ignore-package-versions` to ignore package version-only drift (upgrades/downgrades)
+- `--enforce` to apply the **old** harvest state locally (requires `ansible-playbook` on `PATH`)
+
+**Noise suppression**
+- `--exclude-path` is useful for things that change often but you still want in the harvest baseline (e.g. `/var/anacron`).
+- `--ignore-package-versions` keeps routine upgrades from alerting; package add/remove drift is still reported.
+
+**Enforcement (`--enforce`)**
+If a diff exists and `ansible-playbook` is available, Enroll will:
+1) generate a manifest from the **old** harvest into a temporary directory
+2) run `ansible-playbook -i localhost, -c local <tmp>/playbook.yml` (often with `--tags role_<...>` to limit runtime)
+3) record in the diff report that the old harvest was enforced
+
+Enforcement is intentionally “safe”:
+- reinstalls packages that were removed (`state: present`), but does **not** attempt downgrades/pinning
+- restores users, files (contents + permissions/ownership), and service enable/start state
+
+If `ansible-playbook` is not on `PATH`, Enroll returns an error and does not enforce.
+
 
 **Output formats**
 - `--format json` (default for webhooks)
@@ -143,6 +196,72 @@ Compare two harvest bundles and report what changed.
 
 ---
 
+### `enroll explain`
+Analyze a harvest and provide user-friendly explanations for what's in it and why.
+
+This may also explain why something *wasn't* included (e.g a binary file, a file that was too large, unreadable due to permissions, or looked like a log file/secret.
+
+Provide either the path to the harvest or the path to its state.json. It can also handle SOPS-encrypted harvests.
+
+Output can be provided in plaintext or json.
+
+---
+
+### `enroll validate`
+
+Validates a harvest by checking:
+
+ * state.json exists and is valid JSON
+ * state.json validates against a JSON Schema (by default the vendored one)
+ * Every `managed_file` entry has a corresponding artifact at: `artifacts/<role_name>/<src_rel>`
+ * That there are no **unreferenced files** sitting in `artifacts/` that aren't in the state.
+
+#### Schema location + overrides
+
+The master schema lives at: `enroll/schema/state.schema.json`.
+
+You can override with a local file or URL:
+
+```
+enroll validate /path/to/harvest --schema ./state.schema.json
+enroll validate /path/to/harvest --schema https://enroll.sh/schema/state.schema.json
+```
+
+Or skip schema checks (still does artifact consistency checks):
+
+```
+enroll validate /path/to/harvest --no-schema
+```
+
+#### CLI usage examples
+
+Validate a local harvest:
+
+```
+enroll validate ./harvest
+```
+
+Validate a harvest tarball or a sops bundle:
+
+```
+enroll validate ./harvest.tar.gz
+enroll validate ./harvest.sops --sops
+```
+
+JSON output + write to file:
+
+```
+enroll validate ./harvest --format json --out validate.json
+```
+
+Return exit code 1 for any warnings, not just errors (useful for CI):
+
+```
+enroll validate ./harvest --fail-on-warnings
+```
+
+---
+
 ## Sensitive data
 
 By default, `enroll` does **not** assume how you handle secrets in Ansible. It will attempt to avoid harvesting likely sensitive data (private keys, passwords, tokens, etc.). This can mean it skips some config files you may ultimately want to manage.
@@ -191,7 +310,7 @@ sudo apt update
 sudo apt install enroll
 ```
 
-### Fedora 42
+## Fedora
 
 ```bash
 sudo rpm --import https://mig5.net/static/mig5.asc
@@ -199,7 +318,7 @@ sudo rpm --import https://mig5.net/static/mig5.asc
 sudo tee /etc/yum.repos.d/mig5.repo > /dev/null << 'EOF'
 [mig5]
 name=mig5 Repository
-baseurl=https://rpm.mig5.net/rpm/$basearch
+baseurl=https://rpm.mig5.net/$releasever/rpm/$basearch
 enabled=1
 gpgcheck=1
 repo_gpgcheck=1
@@ -255,6 +374,14 @@ enroll harvest --out /tmp/enroll-harvest
 enroll harvest --remote-host myhost.example.com --remote-user myuser --out /tmp/enroll-harvest
 ```
 
+### Remote harvest over SSH, where the SSH configuration is in ~/.ssh/config (e.g a different SSH key)
+
+Note: you must still pass `--remote-host`, but in this case, its value can be the 'Host' alias of an entry in your `~/.ssh/config`.
+
+```bash
+enroll harvest --remote-host myhostalias --remote-ssh-config ~/.ssh/config --out /tmp/enroll-harvest
+```
+
 ### Include paths (`--include-path`)
 ```bash
 # Add a few dotfiles from /home (still secret-safe unless --dangerous)
@@ -330,7 +457,7 @@ enroll single-shot --remote-host myhost.example.com --remote-user myuser   --har
 
 ## Diff
 
-### Compare two harvest directories
+### Compare two harvest directories, output in json
 ```bash
 enroll diff --old /path/to/harvestA --new /path/to/harvestB --format json
 ```
@@ -342,6 +469,82 @@ enroll diff   --old /path/to/golden/harvest   --new /path/to/new/harvest   --web
 
 `diff` mode also supports email sending and text or markdown format, as well as `--exit-code` mode to trigger a return code of 2 (useful for crons or CI)
 
+### Ignore a specific directory or file from the diff
+```bash
+enroll diff --old /path/to/harvestA --new /path/to/harvestB --exclude-path /var/anacron
+```
+
+### Ignore package version drift (routine upgrades) but still alert on add/remove
+```bash
+enroll diff --old /path/to/harvestA --new /path/to/harvestB --ignore-package-versions
+```
+
+### Enforce the old harvest state when drift is detected (requires Ansible)
+```bash
+enroll diff --old /path/to/harvestA --new /path/to/harvestB --enforce --ignore-package-versions --exclude-path /var/anacron
+```
+
+---
+
+## Explain
+
+### Explain a harvest
+
+All of these do the same thing:
+
+```bash
+enroll explain /path/to/state.json
+enroll explain /path/to/bundle_dir
+enroll explain /path/to/harvest.tar.gz
+```
+
+### Explain a SOPS-encrypted harvest
+
+```bash
+enroll explain /path/to/harvest.tar.gz.sops --sops
+```
+
+### Explain with JSON output and more examples
+
+```bash
+enroll explain /path/to/state.json --format json --max-examples 25
+```
+
+### Example output
+
+```
+❯ enroll explain /tmp/syrah.harvest
+Enroll explain: /tmp/syrah.harvest
+Host: syrah.mig5.net (os: debian, pkg: dpkg)
+Enroll: 0.2.3
+
+Inventory
+- Packages: 254
+- Why packages were included (observed_via):
+  - user_installed: 248 – Package appears explicitly installed (as opposed to only pulled in as a dependency).
+  - package_role: 232 – Package was referenced by an enroll packages snapshot/role. (e.g. acl, acpid, adduser)
+  - systemd_unit: 22 – Package is associated with a systemd unit that was harvested. (e.g. postfix.service, tor.service, apparmor.service)
+
+Roles collected
+- users: 1 user(s), 1 file(s), 0 excluded
+- services: 19 unit(s), 111 file(s), 6 excluded
+- packages: 232 package snapshot(s), 41 file(s), 0 excluded
+- apt_config: 26 file(s), 7 dir(s), 10 excluded
+- dnf_config: 0 file(s), 0 dir(s), 0 excluded
+- etc_custom: 70 file(s), 20 dir(s), 0 excluded
+- usr_local_custom: 35 file(s), 1 dir(s), 0 excluded
+- extra_paths: 0 file(s), 0 dir(s), 0 excluded
+
+Why files were included (managed_files.reason)
+- custom_unowned (179): A file not owned by any package (often custom/operator-managed).. Examples: /etc/apparmor.d/local/lsb_release, /etc/apparmor.d/local/nvidia_modprobe, /etc/apparmor.d/local/sbin.dhclient
+- usr_local_bin_script (35): Executable scripts under /usr/local/bin (often operator-installed).. Examples: /usr/local/bin/check_firewall, /usr/local/bin/awslogs
+- apt_keyring (13): Repository signing key material used by APT.. Examples: /etc/apt/keyrings/openvpn-repo-public.asc, /etc/apt/trusted.gpg, /etc/apt/trusted.gpg.d/deb.torproject.org-keyring.gpg
+- modified_conffile (10): A package-managed conffile differs from the packaged/default version.. Examples: /etc/dnsmasq.conf, /etc/ssh/moduli, /etc/tor/torrc
+- logrotate_snippet (9): logrotate snippets/configs referenced in system configuration.. Examples: /etc/logrotate.d/rsyslog, /etc/logrotate.d/tor, /etc/logrotate.d/apt
+- apt_config (7): APT configuration affecting package installation and repository behavior.. Examples: /etc/apt/apt.conf.d/01autoremove, /etc/apt/apt.conf.d/20listchanges, /etc/apt/apt.conf.d/70debconf
+[...]
+```
+
 ---
 
 ## Run Ansible
@@ -356,6 +559,12 @@ ansible-playbook -i "localhost," -c local /tmp/enroll-ansible/playbook.yml
 ansible-playbook /tmp/enroll-ansible/playbooks/"$(hostname -f)".yml
 ```
 
+### Run only specific roles (tags)
+Generated playbooks tag each role as `role_<name>` (e.g. `role_users`, `role_services`), so you can speed up targeted runs:
+```bash
+ansible-playbook -i "localhost," -c local /tmp/enroll-ansible/playbook.yml --tags role_users
+```
+
 ## Configuration file
 
 As can be seen above, there are a lot of powerful 'permutations' available to all four subcommands.
@@ -405,6 +614,12 @@ exclude_path = /usr/local/bin/docker-*, /usr/local/bin/some-tool
 no_jinjaturtle = true
 sops = 00AE817C24A10C2540461A9C1D7CDE0234DB458D
 
+[diff]
+# ignore noisy drift
+exclude_path = /var/anacron
+ignore_package_versions = true
+# enforce = true  # requires ansible-playbook on PATH
+
 [single-shot]
 # if you use single-shot, put its defaults here.
 # It does not inherit those of the subsections above, so you

debian/changelog

@@ -1,3 +1,68 @@
+enroll (0.4.4) unstable; urgency=medium
+
+ * Add capability to handle passphrases on encrypted SSH private keys. Prompting can be forced with `--ask-key-passphrase` or automated (e.g for CI) with `--ssh-key-passphrase env SOMEVAR`
+
+ -- Miguel Jacq <mig@mig5.net>  Tue, 17 Feb 2026 11:00 +1100
+
+enroll (0.4.3) unstable; urgency=medium
+
+ *  Add support for AddressFamily and ConnectTimeout in the .ssh/config when using `--remote-ssh-config`.
+
+ -- Miguel Jacq <mig@mig5.net>  Fri, 16 Jan 2026 11:00 +1100
+
+enroll (0.4.2) unstable; urgency=medium
+
+ * Support `--remote-ssh-config [path-to-ssh-config]` as an argument in case extra params are required beyond `--remote-port` or `--remote-user`. Note: `--remote-host` must still be set, but it can be an 'alias' represented by the 'Host' value in the ssh config.
+
+ -- Miguel Jacq <mig@mig5.net>  Tue, 13 Jan 2026 21:55:00 +1100
+
+enroll (0.4.1) unstable; urgency=medium
+ * Add interactive output when 'enroll diff --enforce' is invoking Ansible.
+
+ -- Miguel Jacq <mig@mig5.net>  Sun, 11 Jan 2026 10:00:00 +1100
+
+enroll (0.4.0) unstable; urgency=medium
+ * Introduce `enroll validate` - a tool to validate a harvest against the state schema, or check for missing or orphaned obsolete artifacts in a harvest.
+ * Attempt to generate Jinja2 templates of systemd unit files and Postfix main.cf (now that JinjaTurtle supports it)
+ * Update pynacl dependency to resolve CVE-2025-69277
+ * Add `--exclude-path` to `enroll diff` command, so that you can ignore certain churn from the diff (stuff you still wanted to harvest as a baseline but don't care if it changes day to day)
+ * Add `--ignore-package-versions` to `enroll diff` command, to optionally ignore package upgrades (e.g due to patching) from the diff.
+ * Add tags to the playbook for each role, to allow easier targeting of specific roles during play later.
+ * Add `--enforce` mode to `enroll diff`. If there is diff detected between the two harvests, and it can enforce restoring the state from the older harvest, it will manifest the state and apply it with ansible.
+Only the specific roles that had diffed will be applied (via the new tags capability)
+
+ -- Miguel Jacq <mig@mig5.net>  Sat, 10 Jan 2026 10:30:00 +1100
+
+enroll (0.3.0) unstable; urgency=medium
+
+  * Introduce `enroll explain` - a tool to analyze and explain what's in (or not in) a harvest and why.
+  * Centralise the cron and logrotate stuff into their respective roles, we had a bit of duplication between roles based on harvest discovery.
+  * Capture other files in the user's home directory such as `.bashrc`, `.bash_aliases`, `.profile`, if these files differ from the `/etc/skel` defaults
+  * Ignore files that end with a tilde or - (probably backup files generated by editors or shadow file changes)
+  * Manage certain symlinks e.g for apache2/nginx sites-enabled and so on
+
+ -- Miguel Jacq <mig@mig5.net>  Mon, 05 Jan 2026 17:00:00 +1100
+
+enroll (0.2.3) unstable; urgency=medium
+
+  * Introduce --ask-become-pass or -K to support password-required sudo on remote hosts, just like Ansible. It will also fall back to this prompt if a password is required but the arg wasn't passed in.
+
+ -- Miguel Jacq <mig@mig5.net>  Sun, 04 Jan 2026 20:38:00 +1100
+
+enroll (0.2.2) unstable; urgency=medium
+
+  * Fix stat() of parent directory so that we set directory perms correct on --include paths.
+  * Set pty for remote calls when sudo is required, to help systems with limits on sudo without pty
+
+ -- Miguel Jacq <mig@mig5.net>  Sat, 03 Jan 2026 09:56:00 +1100
+
+enroll (0.2.1) unstable; urgency=medium
+
+  * Don't accidentally add extra_paths role to usr_local_custom list, resulting in extra_paths appearing twice in manifested playbook
+  * Ensure directories in the tree of anything included with --include are defined in the state and manifest so we make dirs before we try to create files
+
+ -- Miguel Jacq <mig@mig5.net>  Fri, 02 Jan 2026 21:30:00 +1100
+
 enroll (0.2.0) unstable; urgency=medium
 
   * Add version CLI arg

debian/control

@@ -10,12 +10,13 @@ Build-Depends:
  python3-all,
  python3-yaml,
  python3-poetry-core,
- python3-paramiko
+ python3-paramiko,
+ python3-jsonschema
 Standards-Version: 4.6.2
 Homepage: https://git.mig5.net/mig5/enroll
 
 Package: enroll
 Architecture: all
-Depends: ${misc:Depends}, ${python3:Depends}, python3-yaml, python3-paramiko
+Depends: ${misc:Depends}, ${python3:Depends}, python3-yaml, python3-paramiko, python3-jsonschema
 Description: Harvest a host into Ansible roles
  A tool that inspects a system and emits Ansible roles/playbooks to reproduce it.

enroll/cli.py

@@ -2,6 +2,7 @@ from __future__ import annotations
 
 import argparse
 import configparser
+import json
 import os
 import sys
 import tarfile
@@ -10,11 +11,24 @@ from pathlib import Path
 from typing import Optional
 
 from .cache import new_harvest_cache_dir
-from .diff import compare_harvests, format_report, post_webhook, send_email
+from .diff import (
+    compare_harvests,
+    enforce_old_harvest,
+    format_report,
+    has_enforceable_drift,
+    post_webhook,
+    send_email,
+)
+from .explain import explain_state
 from .harvest import harvest
 from .manifest import manifest
-from .remote import remote_harvest
+from .remote import (
+    remote_harvest,
+    RemoteSudoPasswordRequired,
+    RemoteSSHKeyPassphraseRequired,
+)
 from .sopsutil import SopsError, encrypt_file_binary
+from .validate import validate_harvest
 from .version import get_enroll_version
 
 
@@ -340,16 +354,62 @@ def _add_remote_args(p: argparse.ArgumentParser) -> None:
         "--remote-host",
         help="SSH host to run harvesting on (if set, harvest runs remotely and is pulled locally).",
     )
+    p.add_argument(
+        "--remote-ssh-config",
+        nargs="?",
+        const=str(Path.home() / ".ssh" / "config"),
+        default=None,
+        help=(
+            "Use OpenSSH-style ssh_config settings for --remote-host. "
+            "If provided without a value, defaults to ~/.ssh/config. "
+            "(Applies HostName/User/Port/IdentityFile/ProxyCommand/HostKeyAlias when supported.)"
+        ),
+    )
     p.add_argument(
         "--remote-port",
         type=int,
-        default=22,
-        help="SSH port for --remote-host (default: 22).",
+        default=None,
+        help=(
+            "SSH port for --remote-host. If omitted, defaults to 22, or a value from ssh_config when "
+            "--remote-ssh-config is set."
+        ),
     )
     p.add_argument(
         "--remote-user",
-        default=os.environ.get("USER") or None,
-        help="SSH username for --remote-host (default: local $USER).",
+        default=None,
+        help=(
+            "SSH username for --remote-host. If omitted, defaults to local $USER, or a value from ssh_config when "
+            "--remote-ssh-config is set."
+        ),
+    )
+
+    # Align terminology with Ansible: "become" == sudo.
+    p.add_argument(
+        "--ask-become-pass",
+        "-K",
+        action="store_true",
+        help=(
+            "Prompt for the remote sudo (become) password when using --remote-host "
+            "(similar to ansible --ask-become-pass)."
+        ),
+    )
+
+    keyp = p.add_mutually_exclusive_group()
+    keyp.add_argument(
+        "--ask-key-passphrase",
+        action="store_true",
+        help=(
+            "Prompt for the SSH private key passphrase when using --remote-host. "
+            "If not set, enroll will still prompt on-demand if it detects an encrypted key in an interactive session."
+        ),
+    )
+    keyp.add_argument(
+        "--ssh-key-passphrase-env",
+        metavar="ENV_VAR",
+        help=(
+            "Read the SSH private key passphrase from environment variable ENV_VAR "
+            "(useful for non-interactive runs/CI)."
+        ),
     )
 
 
@@ -536,6 +596,33 @@ def main() -> None:
         default="text",
         help="Report output format (default: text).",
     )
+    d.add_argument(
+        "--exclude-path",
+        action="append",
+        default=[],
+        metavar="PATTERN",
+        help=(
+            "Exclude file paths from the diff report (repeatable). Supports globs (including '**') and regex via 're:<regex>'. "
+            "This affects file drift reporting only (added/removed/changed files), not package/service/user diffs."
+        ),
+    )
+    d.add_argument(
+        "--ignore-package-versions",
+        action="store_true",
+        help=(
+            "Ignore package version changes in the diff report and exit status. "
+            "Package additions/removals are still reported. Useful when routine upgrades would otherwise create noisy drift."
+        ),
+    )
+    d.add_argument(
+        "--enforce",
+        action="store_true",
+        help=(
+            "If differences are detected, attempt to enforce the old harvest state locally by generating a manifest and "
+            "running ansible-playbook. Requires ansible-playbook on PATH. "
+            "Enroll does not attempt to downgrade packages; if the only drift is package version upgrades (or newly installed packages), enforcement is skipped."
+        ),
+    )
     d.add_argument(
         "--out",
         help="Write the report to this file instead of stdout.",
@@ -594,6 +681,75 @@ def main() -> None:
         help="Environment variable containing SMTP password (optional).",
     )
 
+    e = sub.add_parser("explain", help="Explain a harvest state.json")
+    _add_config_args(e)
+    e.add_argument(
+        "harvest",
+        help=(
+            "Harvest input (directory, a path to state.json, a tarball, or a SOPS-encrypted bundle)."
+        ),
+    )
+    e.add_argument(
+        "--sops",
+        action="store_true",
+        help="Treat the input as a SOPS-encrypted bundle (auto-detected if the filename ends with .sops).",
+    )
+    e.add_argument(
+        "--format",
+        choices=["text", "json"],
+        default="text",
+        help="Output format.",
+    )
+    e.add_argument(
+        "--max-examples",
+        type=int,
+        default=3,
+        help="How many example paths/refs to show per reason.",
+    )
+
+    v = sub.add_parser(
+        "validate", help="Validate a harvest bundle (state.json + artifacts)"
+    )
+    _add_config_args(v)
+    v.add_argument(
+        "harvest",
+        help=(
+            "Harvest input (directory, a path to state.json, a tarball, or a SOPS-encrypted bundle)."
+        ),
+    )
+    v.add_argument(
+        "--sops",
+        action="store_true",
+        help="Treat the input as a SOPS-encrypted bundle (auto-detected if the filename ends with .sops).",
+    )
+    v.add_argument(
+        "--schema",
+        help=(
+            "Optional JSON schema source (file path or https:// URL). "
+            "If omitted, uses the schema vendored in the enroll codebase."
+        ),
+    )
+    v.add_argument(
+        "--no-schema",
+        action="store_true",
+        help="Skip JSON schema validation and only perform bundle consistency checks.",
+    )
+    v.add_argument(
+        "--fail-on-warnings",
+        action="store_true",
+        help="Exit non-zero if validation produces warnings.",
+    )
+    v.add_argument(
+        "--format",
+        choices=["text", "json"],
+        default="text",
+        help="Output format.",
+    )
+    v.add_argument(
+        "--out",
+        help="Write the report to this file instead of stdout.",
+    )
+
     argv = sys.argv[1:]
     cfg_path = _discover_config_path(argv)
     argv = _inject_config_argv(
@@ -605,10 +761,23 @@ def main() -> None:
             "manifest": m,
             "single-shot": s,
             "diff": d,
+            "explain": e,
+            "validate": v,
         },
     )
     args = ap.parse_args(argv)
 
+    # Preserve historical defaults for remote harvesting unless ssh_config lookup is enabled.
+    # This lets ssh_config values take effect when the user did not explicitly set
+    # --remote-user / --remote-port.
+    if hasattr(args, "remote_host"):
+        rsc = getattr(args, "remote_ssh_config", None)
+        if not rsc:
+            if getattr(args, "remote_port", None) is None:
+                setattr(args, "remote_port", 22)
+            if getattr(args, "remote_user", None) is None:
+                setattr(args, "remote_user", os.environ.get("USER") or None)
+
     try:
         if args.cmd == "harvest":
             sops_fps = getattr(args, "sops", None)
@@ -623,10 +792,16 @@ def main() -> None:
                         except OSError:
                             pass
                         remote_harvest(
+                            ask_become_pass=args.ask_become_pass,
+                            ask_key_passphrase=bool(args.ask_key_passphrase),
+                            ssh_key_passphrase_env=getattr(
+                                args, "ssh_key_passphrase_env", None
+                            ),
                             local_out_dir=tmp_bundle,
                             remote_host=args.remote_host,
-                            remote_port=int(args.remote_port),
+                            remote_port=args.remote_port,
                             remote_user=args.remote_user,
+                            remote_ssh_config=args.remote_ssh_config,
                             dangerous=bool(args.dangerous),
                             no_sudo=bool(args.no_sudo),
                             include_paths=list(getattr(args, "include_path", []) or []),
@@ -643,10 +818,16 @@ def main() -> None:
                         else new_harvest_cache_dir(hint=args.remote_host).dir
                     )
                     state = remote_harvest(
+                        ask_become_pass=args.ask_become_pass,
+                        ask_key_passphrase=bool(args.ask_key_passphrase),
+                        ssh_key_passphrase_env=getattr(
+                            args, "ssh_key_passphrase_env", None
+                        ),
                         local_out_dir=out_dir,
                         remote_host=args.remote_host,
-                        remote_port=int(args.remote_port),
+                        remote_port=args.remote_port,
                         remote_user=args.remote_user,
+                        remote_ssh_config=args.remote_ssh_config,
                         dangerous=bool(args.dangerous),
                         no_sudo=bool(args.no_sudo),
                         include_paths=list(getattr(args, "include_path", []) or []),
@@ -689,6 +870,42 @@ def main() -> None:
                         exclude_paths=list(getattr(args, "exclude_path", []) or []),
                     )
                     print(path)
+        elif args.cmd == "explain":
+            out = explain_state(
+                args.harvest,
+                sops_mode=bool(getattr(args, "sops", False)),
+                fmt=str(getattr(args, "format", "text")),
+                max_examples=int(getattr(args, "max_examples", 3)),
+            )
+            sys.stdout.write(out)
+
+        elif args.cmd == "validate":
+            res = validate_harvest(
+                args.harvest,
+                sops_mode=bool(getattr(args, "sops", False)),
+                schema=getattr(args, "schema", None),
+                no_schema=bool(getattr(args, "no_schema", False)),
+            )
+
+            fmt = str(getattr(args, "format", "text"))
+            if fmt == "json":
+                txt = json.dumps(res.to_dict(), indent=2, sort_keys=True) + "\n"
+            else:
+                txt = res.to_text()
+
+            out_path = getattr(args, "out", None)
+            if out_path:
+                p = Path(out_path).expanduser()
+                p.parent.mkdir(parents=True, exist_ok=True)
+                p.write_text(txt, encoding="utf-8")
+            else:
+                sys.stdout.write(txt)
+
+            if res.errors:
+                raise SystemExit(1)
+            if res.warnings and bool(getattr(args, "fail_on_warnings", False)):
+                raise SystemExit(1)
+
         elif args.cmd == "manifest":
             out_enc = manifest(
                 args.harvest,
@@ -704,8 +921,47 @@ def main() -> None:
                 args.old,
                 args.new,
                 sops_mode=bool(getattr(args, "sops", False)),
+                exclude_paths=list(getattr(args, "exclude_path", []) or []),
+                ignore_package_versions=bool(
+                    getattr(args, "ignore_package_versions", False)
+                ),
             )
 
+            # Optional enforcement: if drift is detected, attempt to restore the
+            # system to the *old* (baseline) state using ansible-playbook.
+            if bool(getattr(args, "enforce", False)):
+                if has_changes:
+                    if not has_enforceable_drift(report):
+                        report["enforcement"] = {
+                            "requested": True,
+                            "status": "skipped",
+                            "reason": (
+                                "no enforceable drift detected (only additions and/or package version changes); "
+                                "enroll does not attempt to downgrade packages"
+                            ),
+                        }
+                    else:
+                        try:
+                            info = enforce_old_harvest(
+                                args.old,
+                                sops_mode=bool(getattr(args, "sops", False)),
+                                report=report,
+                            )
+                        except Exception as e:
+                            raise SystemExit(
+                                f"error: could not enforce old harvest state: {e}"
+                            ) from e
+                        report["enforcement"] = {
+                            "requested": True,
+                            **(info or {}),
+                        }
+                else:
+                    report["enforcement"] = {
+                        "requested": True,
+                        "status": "skipped",
+                        "reason": "no differences detected",
+                    }
+
             txt = format_report(report, fmt=str(getattr(args, "format", "text")))
             out_path = getattr(args, "out", None)
             if out_path:
@@ -769,10 +1025,16 @@ def main() -> None:
                         except OSError:
                             pass
                         remote_harvest(
+                            ask_become_pass=args.ask_become_pass,
+                            ask_key_passphrase=bool(args.ask_key_passphrase),
+                            ssh_key_passphrase_env=getattr(
+                                args, "ssh_key_passphrase_env", None
+                            ),
                             local_out_dir=tmp_bundle,
                             remote_host=args.remote_host,
-                            remote_port=int(args.remote_port),
+                            remote_port=args.remote_port,
                             remote_user=args.remote_user,
+                            remote_ssh_config=args.remote_ssh_config,
                             dangerous=bool(args.dangerous),
                             no_sudo=bool(args.no_sudo),
                             include_paths=list(getattr(args, "include_path", []) or []),
@@ -798,10 +1060,16 @@ def main() -> None:
                         else new_harvest_cache_dir(hint=args.remote_host).dir
                     )
                     remote_harvest(
+                        ask_become_pass=args.ask_become_pass,
+                        ask_key_passphrase=bool(args.ask_key_passphrase),
+                        ssh_key_passphrase_env=getattr(
+                            args, "ssh_key_passphrase_env", None
+                        ),
                         local_out_dir=harvest_dir,
                         remote_host=args.remote_host,
-                        remote_port=int(args.remote_port),
+                        remote_port=args.remote_port,
                         remote_user=args.remote_user,
+                        remote_ssh_config=args.remote_ssh_config,
                         dangerous=bool(args.dangerous),
                         no_sudo=bool(args.no_sudo),
                         include_paths=list(getattr(args, "include_path", []) or []),
@@ -862,55 +1130,17 @@ def main() -> None:
                         fqdn=args.fqdn,
                         jinjaturtle=_jt_mode(args),
                     )
-        elif args.cmd == "diff":
-            report, has_changes = compare_harvests(
-                args.old, args.new, sops_mode=bool(getattr(args, "sops", False))
-            )
-
-            rendered = format_report(report, fmt=str(args.format))
-            if args.out:
-                Path(args.out).expanduser().write_text(rendered, encoding="utf-8")
-            else:
-                print(rendered, end="")
-
-            do_notify = bool(has_changes or getattr(args, "notify_always", False))
-
-            if do_notify and getattr(args, "webhook", None):
-                wf = str(getattr(args, "webhook_format", "json"))
-                body = format_report(report, fmt=wf).encode("utf-8")
-                headers = {"User-Agent": "enroll"}
-                if wf == "json":
-                    headers["Content-Type"] = "application/json"
-                else:
-                    headers["Content-Type"] = "text/plain; charset=utf-8"
-                for hv in getattr(args, "webhook_header", []) or []:
-                    if ":" not in hv:
-                        raise SystemExit(
-                            "error: --webhook-header must be in the form 'K:V'"
-                        )
-                    k, v = hv.split(":", 1)
-                    headers[k.strip()] = v.strip()
-                status, _ = post_webhook(str(args.webhook), body, headers=headers)
-                if status and status >= 400:
-                    raise SystemExit(f"error: webhook returned HTTP {status}")
-
-            if do_notify and (getattr(args, "email_to", []) or []):
-                subject = getattr(args, "email_subject", None) or "enroll diff report"
-                smtp_password = None
-                pw_env = getattr(args, "smtp_password_env", None)
-                if pw_env:
-                    smtp_password = os.environ.get(str(pw_env))
-                send_email(
-                    to_addrs=list(getattr(args, "email_to", []) or []),
-                    subject=str(subject),
-                    body=rendered,
-                    from_addr=getattr(args, "email_from", None),
-                    smtp=getattr(args, "smtp", None),
-                    smtp_user=getattr(args, "smtp_user", None),
-                    smtp_password=smtp_password,
-                )
-
-            if getattr(args, "exit_code", False) and has_changes:
-                raise SystemExit(2)
+    except RemoteSudoPasswordRequired:
+        raise SystemExit(
+            "error: remote sudo requires a password. Re-run with --ask-become-pass."
+        ) from None
+    except RemoteSSHKeyPassphraseRequired as e:
+        msg = str(e).strip() or (
+            "SSH private key passphrase is required. "
+            "Re-run with --ask-key-passphrase or --ssh-key-passphrase-env VAR."
+        )
+        raise SystemExit(f"error: {msg}") from None
+    except RuntimeError as e:
+        raise SystemExit(f"error: {e}") from None
     except SopsError as e:
-        raise SystemExit(f"error: {e}")
+        raise SystemExit(f"error: {e}") from None

enroll/diff.py

@@ -3,10 +3,15 @@ from __future__ import annotations
 import hashlib
 import json
 import os
+import re
 import shutil
 import subprocess  # nosec
 import tarfile
 import tempfile
+import sys
+import threading
+import time
+import itertools
 import urllib.request
 from contextlib import ExitStack
 from dataclasses import dataclass
@@ -16,9 +21,73 @@ from pathlib import Path
 from typing import Any, Dict, Iterable, List, Optional, Tuple
 
 from .remote import _safe_extract_tar
+from .pathfilter import PathFilter
 from .sopsutil import decrypt_file_binary_to, require_sops_cmd
 
 
+def _progress_enabled() -> bool:
+    """Return True if we should display interactive progress UI on the CLI.
+
+    We only emit progress when stderr is a TTY, so it won't pollute JSON/text reports
+    captured by systemd, CI, webhooks, etc. Users can also disable this explicitly via
+    ENROLL_NO_PROGRESS=1.
+    """
+    if os.environ.get("ENROLL_NO_PROGRESS", "").strip() in {"1", "true", "yes"}:
+        return False
+    try:
+        return sys.stderr.isatty()
+    except Exception:
+        return False
+
+
+class _Spinner:
+    """A tiny terminal spinner with an elapsed-time counter (stderr-only)."""
+
+    def __init__(self, message: str, *, interval: float = 0.12) -> None:
+        self.message = message.rstrip()
+        self.interval = interval
+        self._stop = threading.Event()
+        self._thread: Optional[threading.Thread] = None
+        self._last_len = 0
+        self._start = 0.0
+
+    def start(self) -> None:
+        if self._thread is not None:
+            return
+        self._start = time.monotonic()
+        self._thread = threading.Thread(
+            target=self._run, name="enroll-spinner", daemon=True
+        )
+        self._thread.start()
+
+    def stop(self, final_line: Optional[str] = None) -> None:
+        self._stop.set()
+        if self._thread is not None:
+            self._thread.join(timeout=1.0)
+
+        # Clear spinner line.
+        try:
+            sys.stderr.write("\r" + (" " * max(self._last_len, 0)) + "\r")
+            if final_line:
+                sys.stderr.write(final_line.rstrip() + "\n")
+            sys.stderr.flush()
+        except Exception:
+            pass  # nosec
+
+    def _run(self) -> None:
+        frames = itertools.cycle("|/-\\")
+        while not self._stop.is_set():
+            elapsed = time.monotonic() - self._start
+            line = f"{self.message} {next(frames)} {elapsed:0.1f}s"
+            try:
+                sys.stderr.write("\r" + line)
+                sys.stderr.flush()
+                self._last_len = max(self._last_len, len(line))
+            except Exception:
+                return
+            self._stop.wait(self.interval)
+
+
 def _utc_now_iso() -> str:
     return datetime.now(tz=timezone.utc).isoformat()
 
@@ -289,6 +358,8 @@ def compare_harvests(
     new_path: str,
     *,
     sops_mode: bool = False,
+    exclude_paths: Optional[List[str]] = None,
+    ignore_package_versions: bool = False,
 ) -> Tuple[Dict[str, Any], bool]:
     """Compare two harvests.
 
@@ -315,17 +386,21 @@ def compare_harvests(
         pkgs_removed = sorted(old_pkgs - new_pkgs)
 
         pkgs_version_changed: List[Dict[str, Any]] = []
+        pkgs_version_changed_ignored_count = 0
         for pkg in sorted(old_pkgs & new_pkgs):
             a = old_inv.get(pkg) or {}
             b = new_inv.get(pkg) or {}
             if _pkg_version_key(a) != _pkg_version_key(b):
-                pkgs_version_changed.append(
-                    {
-                        "package": pkg,
-                        "old": _pkg_version_display(a),
-                        "new": _pkg_version_display(b),
-                    }
-                )
+                if ignore_package_versions:
+                    pkgs_version_changed_ignored_count += 1
+                else:
+                    pkgs_version_changed.append(
+                        {
+                            "package": pkg,
+                            "old": _pkg_version_display(a),
+                            "new": _pkg_version_display(b),
+                        }
+                    )
 
         old_units = _service_units(old_state)
         new_units = _service_units(new_state)
@@ -387,6 +462,17 @@ def compare_harvests(
 
         old_files = _file_index(old_b.dir, old_state)
         new_files = _file_index(new_b.dir, new_state)
+
+        # Optional user-supplied path exclusions (same semantics as harvest --exclude-path),
+        # applied only to file drift reporting.
+        diff_filter = PathFilter(include=(), exclude=exclude_paths or ())
+        if exclude_paths:
+            old_files = {
+                p: r for p, r in old_files.items() if not diff_filter.is_excluded(p)
+            }
+            new_files = {
+                p: r for p, r in new_files.items() if not diff_filter.is_excluded(p)
+            }
         old_paths_set = set(old_files)
         new_paths_set = set(new_files)
 
@@ -462,6 +548,10 @@ def compare_harvests(
 
         report: Dict[str, Any] = {
             "generated_at": _utc_now_iso(),
+            "filters": {
+                "exclude_paths": list(exclude_paths or []),
+                "ignore_package_versions": bool(ignore_package_versions),
+            },
             "old": {
                 "input": old_path,
                 "bundle_dir": str(old_b.dir),
@@ -478,6 +568,9 @@ def compare_harvests(
                 "added": pkgs_added,
                 "removed": pkgs_removed,
                 "version_changed": pkgs_version_changed,
+                "version_changed_ignored_count": int(
+                    pkgs_version_changed_ignored_count
+                ),
             },
             "services": {
                 "enabled_added": units_added,
@@ -513,6 +606,302 @@ def compare_harvests(
         return report, has_changes
 
 
+def has_enforceable_drift(report: Dict[str, Any]) -> bool:
+    """Return True if the diff report contains drift that is safe/meaningful to enforce.
+
+    Enforce mode is intended to restore *state* (files/users/services) and to
+    reinstall packages that were removed.
+
+    It is deliberately conservative about package drift:
+      - Package *version* changes alone are not enforced (no downgrades).
+      - Newly installed packages are not removed.
+
+    This helper lets the CLI decide whether `--enforce` should actually run.
+    """
+
+    pk = report.get("packages", {}) or {}
+    if pk.get("removed"):
+        return True
+
+    sv = report.get("services", {}) or {}
+    # We do not try to disable newly-enabled services; we only restore units
+    # that were enabled in the baseline but are now missing.
+    if sv.get("enabled_removed") or []:
+        return True
+
+    for ch in sv.get("changed", []) or []:
+        changes = ch.get("changes") or {}
+        # Ignore package set drift for enforceability decisions; package
+        # enforcement is handled via reinstalling removed packages, and we
+        # avoid trying to "undo" upgrades/renames.
+        for k in changes.keys():
+            if k != "packages":
+                return True
+
+    us = report.get("users", {}) or {}
+    # We restore baseline users (missing/changed). We do not remove newly-added users.
+    if (us.get("removed") or []) or (us.get("changed") or []):
+        return True
+
+    fl = report.get("files", {}) or {}
+    # We restore baseline files (missing/changed). We do not delete newly-managed files.
+    if (fl.get("removed") or []) or (fl.get("changed") or []):
+        return True
+
+    return False
+
+
+def _role_tag(role: str) -> str:
+    """Return the Ansible tag name for a role (must match manifest generation)."""
+    r = str(role or "").strip()
+    safe = re.sub(r"[^A-Za-z0-9_-]+", "_", r).strip("_")
+    if not safe:
+        safe = "other"
+    return f"role_{safe}"
+
+
+def _enforcement_plan(
+    report: Dict[str, Any],
+    old_state: Dict[str, Any],
+    old_bundle_dir: Path,
+) -> Dict[str, Any]:
+    """Return a best-effort enforcement plan (roles/tags) for this diff report.
+
+    We only plan for drift that the baseline manifest can safely restore:
+      - packages that were removed (reinstall, no downgrades)
+      - baseline users that were removed/changed
+      - baseline files that were removed/changed
+      - baseline systemd units that were disabled/changed
+
+    We do NOT plan to remove newly-added packages/users/files/services.
+    """
+    roles: set[str] = set()
+
+    # --- Packages (only removals)
+    pk = report.get("packages", {}) or {}
+    removed_pkgs = set(pk.get("removed") or [])
+    if removed_pkgs:
+        pkg_to_roles: Dict[str, set[str]] = {}
+
+        for svc in _roles(old_state).get("services") or []:
+            r = str(svc.get("role_name") or "").strip()
+            for p in svc.get("packages", []) or []:
+                if p:
+                    pkg_to_roles.setdefault(str(p), set()).add(r)
+
+        for pr in _roles(old_state).get("packages") or []:
+            r = str(pr.get("role_name") or "").strip()
+            p = pr.get("package")
+            if p:
+                pkg_to_roles.setdefault(str(p), set()).add(r)
+
+        for p in removed_pkgs:
+            for r in pkg_to_roles.get(str(p), set()):
+                if r:
+                    roles.add(r)
+
+    # --- Users (removed/changed)
+    us = report.get("users", {}) or {}
+    if (us.get("removed") or []) or (us.get("changed") or []):
+        u = _roles(old_state).get("users") or {}
+        u_role = str(u.get("role_name") or "users")
+        if u_role:
+            roles.add(u_role)
+
+    # --- Files (removed/changed)
+    fl = report.get("files", {}) or {}
+    file_paths: List[str] = []
+    for e in fl.get("removed", []) or []:
+        if isinstance(e, dict):
+            p = e.get("path")
+        else:
+            p = e
+        if p:
+            file_paths.append(str(p))
+    for e in fl.get("changed", []) or []:
+        if isinstance(e, dict):
+            p = e.get("path")
+        else:
+            p = e
+        if p:
+            file_paths.append(str(p))
+
+    if file_paths:
+        idx = _file_index(old_bundle_dir, old_state)
+        for p in file_paths:
+            rec = idx.get(p)
+            if rec and rec.role:
+                roles.add(str(rec.role))
+
+    # --- Services (enabled_removed + meaningful changes)
+    sv = report.get("services", {}) or {}
+    units: List[str] = []
+    for u in sv.get("enabled_removed", []) or []:
+        if u:
+            units.append(str(u))
+    for ch in sv.get("changed", []) or []:
+        if not isinstance(ch, dict):
+            continue
+        unit = ch.get("unit")
+        changes = ch.get("changes") or {}
+        if unit and any(k != "packages" for k in changes.keys()):
+            units.append(str(unit))
+
+    if units:
+        old_units = _service_units(old_state)
+        for u in units:
+            snap = old_units.get(u)
+            if snap and snap.get("role_name"):
+                roles.add(str(snap.get("role_name")))
+
+    # Drop empty/unknown roles.
+    roles = {r for r in roles if r and str(r).strip() and str(r).strip() != "unknown"}
+
+    tags = sorted({_role_tag(r) for r in roles})
+    return {
+        "roles": sorted(roles),
+        "tags": tags,
+    }
+
+
+def enforce_old_harvest(
+    old_path: str,
+    *,
+    sops_mode: bool = False,
+    report: Optional[Dict[str, Any]] = None,
+) -> Dict[str, Any]:
+    """Enforce the *old* (baseline) harvest state on the current machine.
+
+    When Ansible is available, this:
+      1) renders a temporary manifest from the old harvest, and
+      2) runs ansible-playbook locally to apply it.
+
+    Returns a dict suitable for attaching to the diff report under
+    report['enforcement'].
+    """
+
+    ansible_playbook = shutil.which("ansible-playbook")
+    if not ansible_playbook:
+        raise RuntimeError(
+            "ansible-playbook not found on PATH (cannot enforce; install Ansible)"
+        )
+
+    # Import lazily to avoid heavy import cost and potential CLI cycles.
+    from .manifest import manifest
+
+    started_at = _utc_now_iso()
+
+    with ExitStack() as stack:
+        old_b = _bundle_from_input(old_path, sops_mode=sops_mode)
+        if old_b.tempdir:
+            stack.callback(old_b.tempdir.cleanup)
+
+        old_state = _load_state(old_b.dir)
+
+        plan: Optional[Dict[str, Any]] = None
+        tags: Optional[List[str]] = None
+        roles: List[str] = []
+        if report is not None:
+            plan = _enforcement_plan(report, old_state, old_b.dir)
+            roles = list(plan.get("roles") or [])
+            t = list(plan.get("tags") or [])
+            tags = t if t else None
+
+        with tempfile.TemporaryDirectory(prefix="enroll-enforce-") as td:
+            td_path = Path(td)
+            try:
+                os.chmod(td_path, 0o700)
+            except OSError:
+                pass
+
+            # 1) Generate a manifest in a temp directory.
+            manifest(str(old_b.dir), str(td_path))
+
+            playbook = td_path / "playbook.yml"
+            if not playbook.exists():
+                raise RuntimeError(
+                    f"manifest did not produce expected playbook.yml at {playbook}"
+                )
+
+            # 2) Apply it locally.
+            env = dict(os.environ)
+            cfg = td_path / "ansible.cfg"
+            if cfg.exists():
+                env["ANSIBLE_CONFIG"] = str(cfg)
+
+            cmd = [
+                ansible_playbook,
+                "-i",
+                "localhost,",
+                "-c",
+                "local",
+                str(playbook),
+            ]
+            if tags:
+                cmd.extend(["--tags", ",".join(tags)])
+
+            spinner: Optional[_Spinner] = None
+            p: Optional[subprocess.CompletedProcess[str]] = None
+            t0 = time.monotonic()
+            if _progress_enabled():
+                if tags:
+                    sys.stderr.write(
+                        f"Enforce: running ansible-playbook (tags: {','.join(tags)})\n",
+                    )
+                else:
+                    sys.stderr.write("Enforce: running ansible-playbook\n")
+                sys.stderr.flush()
+                spinner = _Spinner("  ansible-playbook")
+                spinner.start()
+
+            try:
+                p = subprocess.run(
+                    cmd,
+                    cwd=str(td_path),
+                    env=env,
+                    capture_output=True,
+                    text=True,
+                    check=False,
+                )  # nosec
+            finally:
+                if spinner:
+                    elapsed = time.monotonic() - t0
+                    rc = p.returncode if p is not None else None
+                    spinner.stop(
+                        final_line=(
+                            f"Enforce: ansible-playbook finished in {elapsed:0.1f}s"
+                            + (f" (rc={rc})" if rc is not None else ""),
+                        ),
+                    )
+
+            finished_at = _utc_now_iso()
+
+            info: Dict[str, Any] = {
+                "status": "applied" if p.returncode == 0 else "failed",
+                "started_at": started_at,
+                "finished_at": finished_at,
+                "ansible_playbook": ansible_playbook,
+                "command": cmd,
+                "returncode": int(p.returncode),
+            }
+
+            # Record tag selection (if we could attribute drift to specific roles).
+            info["roles"] = roles
+            info["tags"] = list(tags or [])
+            if not tags:
+                info["scope"] = "full_playbook"
+
+            if p.returncode != 0:
+                err = (p.stderr or p.stdout or "").strip()
+                raise RuntimeError(
+                    "ansible-playbook failed"
+                    + (f" (rc={p.returncode})" if p.returncode is not None else "")
+                    + (f": {err}" if err else "")
+                )
+
+            return info
+
+
 def format_report(report: Dict[str, Any], *, fmt: str = "text") -> str:
     fmt = (fmt or "text").lower()
     if fmt == "json":
@@ -532,11 +921,60 @@ def _report_text(report: Dict[str, Any]) -> str:
         f"new: {new.get('input')} (host={new.get('host')}, state_mtime={new.get('state_mtime')})"
     )
 
+    filt = report.get("filters", {}) or {}
+    ex_paths = filt.get("exclude_paths", []) or []
+    if ex_paths:
+        lines.append(f"file exclude patterns: {', '.join(str(p) for p in ex_paths)}")
+
+    if filt.get("ignore_package_versions"):
+        ignored = int(
+            (report.get("packages", {}) or {}).get("version_changed_ignored_count") or 0
+        )
+        msg = "package version drift: ignored (--ignore-package-versions)"
+        if ignored:
+            msg += f" (ignored {ignored} change{'s' if ignored != 1 else ''})"
+        lines.append(msg)
+
+    enf = report.get("enforcement") or {}
+    if enf:
+        lines.append("\nEnforcement")
+        status = str(enf.get("status") or "").strip().lower()
+        if status == "applied":
+            extra = ""
+            tags = enf.get("tags") or []
+            scope = enf.get("scope")
+            if tags:
+                extra = f" (tags={','.join(str(t) for t in tags)})"
+            elif scope:
+                extra = f" ({scope})"
+            lines.append(
+                f"  applied old harvest via ansible-playbook (rc={enf.get('returncode')})"
+                + extra
+                + (
+                    f" (finished {enf.get('finished_at')})"
+                    if enf.get("finished_at")
+                    else ""
+                )
+            )
+        elif status == "failed":
+            lines.append(
+                f"  attempted enforcement but ansible-playbook failed (rc={enf.get('returncode')})"
+            )
+        elif status == "skipped":
+            r = enf.get("reason")
+            lines.append("  skipped" + (f": {r}" if r else ""))
+        else:
+            # Best-effort formatting for future fields.
+            lines.append("  " + json.dumps(enf, sort_keys=True))
+
     pk = report.get("packages", {})
     lines.append("\nPackages")
     lines.append(f"  added:   {len(pk.get('added', []) or [])}")
     lines.append(f"  removed: {len(pk.get('removed', []) or [])}")
-    lines.append(f"  version_changed: {len(pk.get('version_changed', []) or [])}")
+    ignored_v = int(pk.get("version_changed_ignored_count") or 0)
+    vc = len(pk.get("version_changed", []) or [])
+    suffix = f" (ignored {ignored_v})" if ignored_v else ""
+    lines.append(f"  version_changed: {vc}{suffix}")
     for p in pk.get("added", []) or []:
         lines.append(f"    + {p}")
     for p in pk.get("removed", []) or []:
@@ -638,6 +1076,67 @@ def _report_markdown(report: Dict[str, Any]) -> str:
         f"- **New**: `{new.get('input')}` (host={new.get('host')}, state_mtime={new.get('state_mtime')})\n"
     )
 
+    filt = report.get("filters", {}) or {}
+    ex_paths = filt.get("exclude_paths", []) or []
+    if ex_paths:
+        out.append(
+            "- **File exclude patterns**: "
+            + ", ".join(f"`{p}`" for p in ex_paths)
+            + "\n"
+        )
+
+    if filt.get("ignore_package_versions"):
+        ignored = int(
+            (report.get("packages", {}) or {}).get("version_changed_ignored_count") or 0
+        )
+        msg = "- **Package version drift**: ignored (`--ignore-package-versions`)"
+        if ignored:
+            msg += f" (ignored {ignored} change{'s' if ignored != 1 else ''})"
+        out.append(msg + "\n")
+
+    enf = report.get("enforcement") or {}
+    if enf:
+        out.append("\n## Enforcement\n")
+        status = str(enf.get("status") or "").strip().lower()
+        if status == "applied":
+            extra = ""
+            tags = enf.get("tags") or []
+            scope = enf.get("scope")
+            if tags:
+                extra = " (tags=" + ",".join(str(t) for t in tags) + ")"
+            elif scope:
+                extra = f" ({scope})"
+            out.append(
+                "- ✅ Applied old harvest via ansible-playbook"
+                + extra
+                + (
+                    f" (rc={enf.get('returncode')})"
+                    if enf.get("returncode") is not None
+                    else ""
+                )
+                + (
+                    f" (finished `{enf.get('finished_at')}`)"
+                    if enf.get("finished_at")
+                    else ""
+                )
+                + "\n"
+            )
+        elif status == "failed":
+            out.append(
+                "- ⚠️ Attempted enforcement but ansible-playbook failed"
+                + (
+                    f" (rc={enf.get('returncode')})"
+                    if enf.get("returncode") is not None
+                    else ""
+                )
+                + "\n"
+            )
+        elif status == "skipped":
+            r = enf.get("reason")
+            out.append("- Skipped" + (f": {r}" if r else "") + "\n")
+        else:
+            out.append(f"- {json.dumps(enf, sort_keys=True)}\n")
+
     pk = report.get("packages", {})
     out.append("## Packages\n")
     out.append(f"- Added: {len(pk.get('added', []) or [])}\n")
@@ -647,7 +1146,10 @@ def _report_markdown(report: Dict[str, Any]) -> str:
     for p in pk.get("removed", []) or []:
         out.append(f"  - `- {p}`\n")
 
-    out.append(f"- Version changed: {len(pk.get('version_changed', []) or [])}\n")
+    ignored_v = int(pk.get("version_changed_ignored_count") or 0)
+    vc = len(pk.get("version_changed", []) or [])
+    suffix = f" (ignored {ignored_v})" if ignored_v else ""
+    out.append(f"- Version changed: {vc}{suffix}\n")
     for ch in pk.get("version_changed", []) or []:
         out.append(
             f"  - `~ {ch.get('package')}`: `{ch.get('old')}` → `{ch.get('new')}`\n"

enroll/explain.py

@@ -0,0 +1,578 @@
+from __future__ import annotations
+
+import json
+from collections import Counter, defaultdict
+from dataclasses import dataclass
+from typing import Any, Dict, Iterable, List, Tuple
+
+from .diff import _bundle_from_input, _load_state  # reuse existing bundle handling
+
+
+@dataclass(frozen=True)
+class ReasonInfo:
+    title: str
+    why: str
+
+
+_MANAGED_FILE_REASONS: Dict[str, ReasonInfo] = {
+    # Package manager / repo config
+    "apt_config": ReasonInfo(
+        "APT configuration",
+        "APT configuration affecting package installation and repository behavior.",
+    ),
+    "apt_source": ReasonInfo(
+        "APT repository source",
+        "APT source list entries (e.g. sources.list or sources.list.d).",
+    ),
+    "apt_keyring": ReasonInfo(
+        "APT keyring",
+        "Repository signing key material used by APT.",
+    ),
+    "apt_signed_by_keyring": ReasonInfo(
+        "APT Signed-By keyring",
+        "Keyring referenced via a Signed-By directive in an APT source.",
+    ),
+    "yum_conf": ReasonInfo(
+        "YUM/DNF main config",
+        "Primary YUM configuration (often /etc/yum.conf).",
+    ),
+    "yum_config": ReasonInfo(
+        "YUM/DNF config",
+        "YUM/DNF configuration files (including conf.d).",
+    ),
+    "yum_repo": ReasonInfo(
+        "YUM/DNF repository",
+        "YUM/DNF repository definitions (e.g. yum.repos.d).",
+    ),
+    "dnf_config": ReasonInfo(
+        "DNF configuration",
+        "DNF configuration affecting package installation and repositories.",
+    ),
+    "rpm_gpg_key": ReasonInfo(
+        "RPM GPG key",
+        "Repository signing keys used by RPM/YUM/DNF.",
+    ),
+    # SSH
+    "authorized_keys": ReasonInfo(
+        "SSH authorized keys",
+        "User authorized_keys files (controls who can log in with SSH keys).",
+    ),
+    "ssh_public_key": ReasonInfo(
+        "SSH public key",
+        "SSH host/user public keys relevant to authentication.",
+    ),
+    # System config / security
+    "system_security": ReasonInfo(
+        "Security configuration",
+        "Security-sensitive configuration (SSH, sudoers, PAM, auth, etc.).",
+    ),
+    "system_network": ReasonInfo(
+        "Network configuration",
+        "Network configuration (interfaces, resolv.conf, network managers, etc.).",
+    ),
+    "system_firewall": ReasonInfo(
+        "Firewall configuration",
+        "Firewall rules/configuration (ufw, nftables, iptables, etc.).",
+    ),
+    "system_sysctl": ReasonInfo(
+        "sysctl configuration",
+        "Kernel sysctl tuning (sysctl.conf / sysctl.d).",
+    ),
+    "system_modprobe": ReasonInfo(
+        "modprobe configuration",
+        "Kernel module configuration (modprobe.d).",
+    ),
+    "system_mounts": ReasonInfo(
+        "Mount configuration",
+        "Mount configuration (e.g. /etc/fstab and related).",
+    ),
+    "system_rc": ReasonInfo(
+        "Startup/rc configuration",
+        "Startup scripts / rc configuration that can affect boot behavior.",
+    ),
+    # systemd + timers
+    "systemd_dropin": ReasonInfo(
+        "systemd drop-in",
+        "systemd override/drop-in files that modify a unit's behavior.",
+    ),
+    "systemd_envfile": ReasonInfo(
+        "systemd EnvironmentFile",
+        "Files referenced by systemd units via EnvironmentFile.",
+    ),
+    "related_timer": ReasonInfo(
+        "Related systemd timer",
+        "A systemd timer captured because it is related to a unit/service.",
+    ),
+    # cron / logrotate
+    "system_cron": ReasonInfo(
+        "System cron",
+        "System cron configuration (crontab, cron.d, etc.).",
+    ),
+    "cron_snippet": ReasonInfo(
+        "Cron snippet",
+        "Cron snippets referenced/used by harvested services or configs.",
+    ),
+    "system_logrotate": ReasonInfo(
+        "System logrotate",
+        "System logrotate configuration.",
+    ),
+    "logrotate_snippet": ReasonInfo(
+        "logrotate snippet",
+        "logrotate snippets/configs referenced in system configuration.",
+    ),
+    # Custom paths / drift signals
+    "modified_conffile": ReasonInfo(
+        "Modified package conffile",
+        "A package-managed conffile differs from the packaged/default version.",
+    ),
+    "modified_packaged_file": ReasonInfo(
+        "Modified packaged file",
+        "A file owned by a package differs from the packaged version.",
+    ),
+    "custom_unowned": ReasonInfo(
+        "Unowned custom file",
+        "A file not owned by any package (often custom/operator-managed).",
+    ),
+    "custom_specific_path": ReasonInfo(
+        "Custom specific path",
+        "A specific path included by a custom rule or snapshot.",
+    ),
+    "usr_local_bin_script": ReasonInfo(
+        "/usr/local/bin script",
+        "Executable scripts under /usr/local/bin (often operator-installed).",
+    ),
+    "usr_local_etc_custom": ReasonInfo(
+        "/usr/local/etc custom",
+        "Custom configuration under /usr/local/etc.",
+    ),
+    # User includes
+    "user_include": ReasonInfo(
+        "User-included path",
+        "Included because you specified it via --include-path / include patterns.",
+    ),
+}
+
+_MANAGED_DIR_REASONS: Dict[str, ReasonInfo] = {
+    "parent_of_managed_file": ReasonInfo(
+        "Parent directory",
+        "Included so permissions/ownership can be recreated for managed files.",
+    ),
+    "user_include_dir": ReasonInfo(
+        "User-included directory",
+        "Included because you specified it via --include-path / include patterns.",
+    ),
+}
+
+_EXCLUDED_REASONS: Dict[str, ReasonInfo] = {
+    "user_excluded": ReasonInfo(
+        "User excluded",
+        "Excluded because you explicitly excluded it (e.g. --exclude-path / patterns).",
+    ),
+    "unreadable": ReasonInfo(
+        "Unreadable",
+        "Enroll could not read this path with the permissions it had.",
+    ),
+    "log_file": ReasonInfo(
+        "Log file",
+        "Excluded because it appears to be a log file (usually noisy/large).",
+    ),
+    "denied_path": ReasonInfo(
+        "Denied path",
+        "Excluded because the path is in a denylist for safety.",
+    ),
+    "too_large": ReasonInfo(
+        "Too large",
+        "Excluded because it exceeded the size limit for harvested files.",
+    ),
+    "not_regular_file": ReasonInfo(
+        "Not a regular file",
+        "Excluded because it was not a regular file (device, socket, etc.).",
+    ),
+    "binary_like": ReasonInfo(
+        "Binary-like",
+        "Excluded because it looked like binary content (not useful for config management).",
+    ),
+    "sensitive_content": ReasonInfo(
+        "Sensitive content",
+        "Excluded because it likely contains secrets (e.g. shadow, private keys).",
+    ),
+}
+
+_OBSERVED_VIA: Dict[str, ReasonInfo] = {
+    "user_installed": ReasonInfo(
+        "User-installed",
+        "Package appears explicitly installed (as opposed to only pulled in as a dependency).",
+    ),
+    "systemd_unit": ReasonInfo(
+        "Referenced by systemd unit",
+        "Package is associated with a systemd unit that was harvested.",
+    ),
+    "package_role": ReasonInfo(
+        "Referenced by package role",
+        "Package was referenced by an enroll packages snapshot/role.",
+    ),
+}
+
+
+def _ri(mapping: Dict[str, ReasonInfo], key: str) -> ReasonInfo:
+    return mapping.get(key) or ReasonInfo(key, f"Captured with reason '{key}'")
+
+
+def _role_common_counts(role_obj: Dict[str, Any]) -> Tuple[int, int, int, int]:
+    """Return (managed_files, managed_dirs, excluded, notes) counts for a RoleCommon object."""
+    mf = len(role_obj.get("managed_files") or [])
+    md = len(role_obj.get("managed_dirs") or [])
+    ex = len(role_obj.get("excluded") or [])
+    nt = len(role_obj.get("notes") or [])
+    return mf, md, ex, nt
+
+
+def _summarize_reasons(
+    items: Iterable[Dict[str, Any]],
+    reason_key: str,
+    *,
+    mapping: Dict[str, ReasonInfo],
+    max_examples: int,
+) -> List[Dict[str, Any]]:
+    by_reason: Dict[str, List[str]] = defaultdict(list)
+    counts: Counter[str] = Counter()
+
+    for it in items:
+        if not isinstance(it, dict):
+            continue
+        r = it.get(reason_key)
+        if not r:
+            continue
+        r = str(r)
+        counts[r] += 1
+        p = it.get("path")
+        if (
+            max_examples > 0
+            and isinstance(p, str)
+            and p
+            and len(by_reason[r]) < max_examples
+        ):
+            by_reason[r].append(p)
+
+    out: List[Dict[str, Any]] = []
+    for reason, count in counts.most_common():
+        info = _ri(mapping, reason)
+        out.append(
+            {
+                "reason": reason,
+                "count": count,
+                "title": info.title,
+                "why": info.why,
+                "examples": by_reason.get(reason, []),
+            }
+        )
+    return out
+
+
+def explain_state(
+    harvest: str,
+    *,
+    sops_mode: bool = False,
+    fmt: str = "text",
+    max_examples: int = 3,
+) -> str:
+    """Explain a harvest bundle's state.json.
+
+    `harvest` may be:
+      - a bundle directory
+      - a path to state.json
+      - a tarball (.tar.gz/.tgz)
+      - a SOPS-encrypted bundle (.sops)
+    """
+    bundle = _bundle_from_input(harvest, sops_mode=sops_mode)
+    state = _load_state(bundle.dir)
+
+    host = state.get("host") or {}
+    enroll = state.get("enroll") or {}
+    roles = state.get("roles") or {}
+    inv = state.get("inventory") or {}
+    inv_pkgs = (inv.get("packages") or {}) if isinstance(inv, dict) else {}
+
+    role_summaries: List[Dict[str, Any]] = []
+
+    # Users
+    users_obj = roles.get("users") or {}
+    user_entries = users_obj.get("users") or []
+    mf, md, ex, _nt = (
+        _role_common_counts(users_obj) if isinstance(users_obj, dict) else (0, 0, 0, 0)
+    )
+    role_summaries.append(
+        {
+            "role": "users",
+            "summary": f"{len(user_entries)} user(s), {mf} file(s), {ex} excluded",
+            "notes": users_obj.get("notes") or [],
+        }
+    )
+
+    # Services
+    services_list = roles.get("services") or []
+    if isinstance(services_list, list):
+        total_mf = sum(
+            len((s.get("managed_files") or []))
+            for s in services_list
+            if isinstance(s, dict)
+        )
+        total_ex = sum(
+            len((s.get("excluded") or [])) for s in services_list if isinstance(s, dict)
+        )
+        role_summaries.append(
+            {
+                "role": "services",
+                "summary": f"{len(services_list)} unit(s), {total_mf} file(s), {total_ex} excluded",
+                "units": [
+                    {
+                        "unit": s.get("unit"),
+                        "active_state": s.get("active_state"),
+                        "sub_state": s.get("sub_state"),
+                        "unit_file_state": s.get("unit_file_state"),
+                        "condition_result": s.get("condition_result"),
+                    }
+                    for s in services_list
+                    if isinstance(s, dict)
+                ],
+            }
+        )
+
+    # Package snapshots
+    pkgs_list = roles.get("packages") or []
+    if isinstance(pkgs_list, list):
+        total_mf = sum(
+            len((p.get("managed_files") or []))
+            for p in pkgs_list
+            if isinstance(p, dict)
+        )
+        total_ex = sum(
+            len((p.get("excluded") or [])) for p in pkgs_list if isinstance(p, dict)
+        )
+        role_summaries.append(
+            {
+                "role": "packages",
+                "summary": f"{len(pkgs_list)} package snapshot(s), {total_mf} file(s), {total_ex} excluded",
+                "packages": [
+                    p.get("package") for p in pkgs_list if isinstance(p, dict)
+                ],
+            }
+        )
+
+    # Single snapshots
+    for rname in [
+        "apt_config",
+        "dnf_config",
+        "etc_custom",
+        "usr_local_custom",
+        "extra_paths",
+    ]:
+        robj = roles.get(rname) or {}
+        if not isinstance(robj, dict):
+            continue
+        mf, md, ex, _nt = _role_common_counts(robj)
+        extra: Dict[str, Any] = {}
+        if rname == "extra_paths":
+            extra = {
+                "include_patterns": robj.get("include_patterns") or [],
+                "exclude_patterns": robj.get("exclude_patterns") or [],
+            }
+        role_summaries.append(
+            {
+                "role": rname,
+                "summary": f"{mf} file(s), {md} dir(s), {ex} excluded",
+                "notes": robj.get("notes") or [],
+                **extra,
+            }
+        )
+
+    # Flatten managed/excluded across roles
+    all_managed_files: List[Dict[str, Any]] = []
+    all_managed_dirs: List[Dict[str, Any]] = []
+    all_excluded: List[Dict[str, Any]] = []
+
+    def _consume_role(role_obj: Dict[str, Any]) -> None:
+        for f in role_obj.get("managed_files") or []:
+            if isinstance(f, dict):
+                all_managed_files.append(f)
+        for d in role_obj.get("managed_dirs") or []:
+            if isinstance(d, dict):
+                all_managed_dirs.append(d)
+        for e in role_obj.get("excluded") or []:
+            if isinstance(e, dict):
+                all_excluded.append(e)
+
+    if isinstance(users_obj, dict):
+        _consume_role(users_obj)
+    if isinstance(services_list, list):
+        for s in services_list:
+            if isinstance(s, dict):
+                _consume_role(s)
+    if isinstance(pkgs_list, list):
+        for p in pkgs_list:
+            if isinstance(p, dict):
+                _consume_role(p)
+    for rname in [
+        "apt_config",
+        "dnf_config",
+        "etc_custom",
+        "usr_local_custom",
+        "extra_paths",
+    ]:
+        robj = roles.get(rname)
+        if isinstance(robj, dict):
+            _consume_role(robj)
+
+    managed_file_reasons = _summarize_reasons(
+        all_managed_files,
+        "reason",
+        mapping=_MANAGED_FILE_REASONS,
+        max_examples=max_examples,
+    )
+    managed_dir_reasons = _summarize_reasons(
+        all_managed_dirs,
+        "reason",
+        mapping=_MANAGED_DIR_REASONS,
+        max_examples=max_examples,
+    )
+    excluded_reasons = _summarize_reasons(
+        all_excluded,
+        "reason",
+        mapping=_EXCLUDED_REASONS,
+        max_examples=max_examples,
+    )
+
+    # Inventory observed_via breakdown (count packages that contain at least one entry for that kind)
+    observed_kinds: Counter[str] = Counter()
+    observed_refs: Dict[str, Counter[str]] = defaultdict(Counter)
+    for _pkg, entry in inv_pkgs.items():
+        if not isinstance(entry, dict):
+            continue
+        seen_kinds = set()
+        for ov in entry.get("observed_via") or []:
+            if not isinstance(ov, dict):
+                continue
+            kind = ov.get("kind")
+            if not kind:
+                continue
+            kind = str(kind)
+            seen_kinds.add(kind)
+            ref = ov.get("ref")
+            if isinstance(ref, str) and ref:
+                observed_refs[kind][ref] += 1
+        for k in seen_kinds:
+            observed_kinds[k] += 1
+
+    observed_via_summary: List[Dict[str, Any]] = []
+    for kind, cnt in observed_kinds.most_common():
+        info = _ri(_OBSERVED_VIA, kind)
+        top_refs = [
+            r for r, _ in observed_refs.get(kind, Counter()).most_common(max_examples)
+        ]
+        observed_via_summary.append(
+            {
+                "kind": kind,
+                "count": cnt,
+                "title": info.title,
+                "why": info.why,
+                "top_refs": top_refs,
+            }
+        )
+
+    report: Dict[str, Any] = {
+        "bundle_dir": str(bundle.dir),
+        "host": host,
+        "enroll": enroll,
+        "inventory": {
+            "package_count": len(inv_pkgs),
+            "observed_via": observed_via_summary,
+        },
+        "roles": role_summaries,
+        "reasons": {
+            "managed_files": managed_file_reasons,
+            "managed_dirs": managed_dir_reasons,
+            "excluded": excluded_reasons,
+        },
+    }
+
+    if fmt == "json":
+        return json.dumps(report, indent=2, sort_keys=True)
+
+    # Text rendering
+    out: List[str] = []
+    out.append(f"Enroll explained: {harvest}")
+    hn = host.get("hostname") or "(unknown host)"
+    os_family = host.get("os") or "unknown"
+    pkg_backend = host.get("pkg_backend") or "?"
+    ver = enroll.get("version") or "?"
+    out.append(f"Host: {hn} (os: {os_family}, pkg: {pkg_backend})")
+    out.append(f"Enroll: {ver}")
+    out.append("")
+
+    out.append("Inventory")
+    out.append(f"- Packages: {len(inv_pkgs)}")
+    if observed_via_summary:
+        out.append("- Why packages were included (observed_via):")
+        for ov in observed_via_summary:
+            extra = ""
+            if ov.get("top_refs"):
+                extra = f" (e.g. {', '.join(ov['top_refs'])})"
+            out.append(f"  - {ov['kind']}: {ov['count']} – {ov['why']}{extra}")
+    out.append("")
+
+    out.append("Roles collected")
+    for rs in role_summaries:
+        out.append(f"- {rs['role']}: {rs['summary']}")
+        if rs["role"] == "extra_paths":
+            inc = rs.get("include_patterns") or []
+            exc = rs.get("exclude_patterns") or []
+            if inc:
+                suffix = "…" if len(inc) > max_examples else ""
+                out.append(
+                    f"    include_patterns: {', '.join(map(str, inc[:max_examples]))}{suffix}"
+                )
+            if exc:
+                suffix = "…" if len(exc) > max_examples else ""
+                out.append(
+                    f"    exclude_patterns: {', '.join(map(str, exc[:max_examples]))}{suffix}"
+                )
+        notes = rs.get("notes") or []
+        if notes:
+            for n in notes[:max_examples]:
+                out.append(f"    note: {n}")
+            if len(notes) > max_examples:
+                out.append(
+                    f"    note: (+{len(notes) - max_examples} more. Use --format json to see them all)"
+                )
+    out.append("")
+
+    out.append("Why files were included (managed_files.reason)")
+    if managed_file_reasons:
+        for r in managed_file_reasons[:15]:
+            exs = r.get("examples") or []
+            ex_txt = f" Examples: {', '.join(exs)}" if exs else ""
+            out.append(f"- {r['reason']} ({r['count']}): {r['why']}.{ex_txt}")
+        if len(managed_file_reasons) > 15:
+            out.append(
+                f"- (+{len(managed_file_reasons) - 15} more reasons. Use --format json to see them all)"
+            )
+    else:
+        out.append("- (no managed files)")
+
+    if managed_dir_reasons:
+        out.append("")
+        out.append("Why directories were included (managed_dirs.reason)")
+        for r in managed_dir_reasons:
+            out.append(f"- {r['reason']} ({r['count']}): {r['why']}")
+
+    out.append("")
+    out.append("Why paths were excluded")
+    if excluded_reasons:
+        for r in excluded_reasons:
+            exs = r.get("examples") or []
+            ex_txt = f" Examples: {', '.join(exs)}" if exs else ""
+            out.append(f"- {r['reason']} ({r['count']}): {r['why']}.{ex_txt}")
+    else:
+        out.append("- (no excluded paths)")
+
+    return "\n".join(out) + "\n"

enroll/fsutil.py

@@ -24,7 +24,7 @@ def stat_triplet(path: str) -> Tuple[str, str, str]:
     mode is a zero-padded octal string (e.g. "0644").
     """
     st = os.stat(path, follow_symlinks=True)
-    mode = oct(st.st_mode & 0o777)[2:].zfill(4)
+    mode = oct(st.st_mode & 0o7777)[2:].zfill(4)
 
     import grp
     import pwd

enroll/harvest.py

@@ -5,8 +5,9 @@ import json
 import os
 import re
 import shutil
+import stat
 import time
-from dataclasses import dataclass, asdict
+from dataclasses import dataclass, asdict, field
 from typing import Dict, List, Optional, Set
 
 from .systemd import (
@@ -34,6 +35,28 @@ class ManagedFile:
     reason: str
 
 
+@dataclass
+class ManagedLink:
+    """A symlink we want to materialise on the target host.
+
+    For configuration enablement patterns (e.g. sites-enabled), the symlink is
+    meaningful state even when the link target is captured elsewhere.
+    """
+
+    path: str
+    target: str
+    reason: str
+
+
+@dataclass
+class ManagedDir:
+    path: str
+    owner: str
+    group: str
+    mode: str
+    reason: str
+
+
 @dataclass
 class ExcludedFile:
     path: str
@@ -49,69 +72,80 @@ class ServiceSnapshot:
     sub_state: Optional[str]
     unit_file_state: Optional[str]
     condition_result: Optional[str]
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    managed_links: List[ManagedLink] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class PackageSnapshot:
     package: str
     role_name: str
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    managed_links: List[ManagedLink] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class UsersSnapshot:
     role_name: str
     users: List[dict]
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class AptConfigSnapshot:
     role_name: str
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class DnfConfigSnapshot:
     role_name: str
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class EtcCustomSnapshot:
     role_name: str
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class UsrLocalCustomSnapshot:
     role_name: str
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 @dataclass
 class ExtraPathsSnapshot:
     role_name: str
-    include_patterns: List[str]
-    exclude_patterns: List[str]
-    managed_files: List[ManagedFile]
-    excluded: List[ExcludedFile]
-    notes: List[str]
+    include_patterns: List[str] = field(default_factory=list)
+    exclude_patterns: List[str] = field(default_factory=list)
+    managed_dirs: List[ManagedDir] = field(default_factory=list)
+    managed_files: List[ManagedFile] = field(default_factory=list)
+    managed_links: List[ManagedLink] = field(default_factory=list)
+    excluded: List[ExcludedFile] = field(default_factory=list)
+    notes: List[str] = field(default_factory=list)
 
 
 ALLOWED_UNOWNED_EXTS = {
@@ -139,6 +173,130 @@ ALLOWED_UNOWNED_EXTS = {
 MAX_FILES_CAP = 4000
 MAX_UNOWNED_FILES_PER_ROLE = 500
 
+
+def _files_differ(a: str, b: str, *, max_bytes: int = 2_000_000) -> bool:
+    """Return True if file `a` differs from file `b`.
+
+    Best-effort and conservative:
+      - If `b` (baseline) does not exist or is not a regular file, treat as
+        "different" so we err on the side of capturing user state.
+      - If we can't stat/read either file, treat as "different" (capture will
+        later be filtered via IgnorePolicy).
+      - If files are large, avoid reading them fully.
+    """
+
+    try:
+        st_a = os.stat(a, follow_symlinks=True)
+    except OSError:
+        return True
+
+    # Refuse to do content comparisons on non-regular files.
+    if not stat.S_ISREG(st_a.st_mode):
+        return True
+
+    try:
+        st_b = os.stat(b, follow_symlinks=True)
+    except OSError:
+        return True
+
+    if not stat.S_ISREG(st_b.st_mode):
+        return True
+
+    if st_a.st_size != st_b.st_size:
+        return True
+
+    # If it's unexpectedly big, treat as different to avoid expensive reads.
+    if st_a.st_size > max_bytes:
+        return True
+
+    try:
+        with open(a, "rb") as fa, open(b, "rb") as fb:
+            while True:
+                ca = fa.read(1024 * 64)
+                cb = fb.read(1024 * 64)
+                if ca != cb:
+                    return True
+                if not ca:  # EOF on both
+                    return False
+    except OSError:
+        return True
+
+
+def _merge_parent_dirs(
+    existing_dirs: List[ManagedDir],
+    managed_files: List[ManagedFile],
+    *,
+    policy: IgnorePolicy,
+    extra_paths: Optional[List[str]] = None,
+) -> List[ManagedDir]:
+    """Ensure parent directories for managed_files are present in managed_dirs.
+
+    This is used so the Ansible manifest can create destination directories with
+    explicit owner/group/mode (ansible-lint friendly) without needing a separate
+    "mkdir without perms" task.
+
+    We only add the immediate parent directory for each managed file. For
+    explicit directory includes (extra_paths), existing_dirs will already
+    contain the walked directory tree.
+    """
+    by_path: Dict[str, ManagedDir] = {
+        d.path: d for d in (existing_dirs or []) if d.path
+    }
+
+    def _iter_paths() -> List[str]:
+        paths: List[str] = []
+        for mf in managed_files or []:
+            if mf and mf.path:
+                paths.append(str(mf.path))
+        for p in extra_paths or []:
+            if p:
+                paths.append(str(p))
+        return paths
+
+    for p0 in _iter_paths():
+        p = str(p0 or "").rstrip("/")
+        if not p:
+            continue
+        dpath = os.path.dirname(p)
+        if not dpath or dpath == "/":
+            continue
+        if dpath in by_path:
+            continue
+
+        # Directory-deny logic: newer IgnorePolicy implementations provide
+        # deny_reason_dir(). Older/simple policies (including unit tests) may
+        # only implement deny_reason(), which is file-oriented and may return
+        # "not_regular_file" for directories.
+        deny = None
+        deny_dir = getattr(policy, "deny_reason_dir", None)
+        if callable(deny_dir):
+            deny = deny_dir(dpath)
+        else:
+            deny = policy.deny_reason(dpath)
+            if deny in ("not_regular_file", "not_file", "not_regular"):
+                deny = None
+        if deny:
+            # If the file itself was captured, its parent directory is likely safe,
+            # but still respect deny globs for directories to avoid managing
+            # sensitive/forbidden trees.
+            continue
+
+        try:
+            owner, group, mode = stat_triplet(dpath)
+        except OSError:
+            continue
+
+        by_path[dpath] = ManagedDir(
+            path=dpath,
+            owner=owner,
+            group=group,
+            mode=mode,
+            reason="parent_of_managed_file",
+        )
+
+    return [by_path[k] for k in sorted(by_path)]
+
+
 # Directories that are shared across many packages.
 # Never attribute all unowned files in these trees
 # to one single package.
@@ -283,6 +441,72 @@ def _capture_file(
     return True
 
 
+def _capture_link(
+    *,
+    role_name: str,
+    abs_path: str,
+    reason: str,
+    policy: IgnorePolicy,
+    path_filter: PathFilter,
+    managed_out: List[ManagedLink],
+    excluded_out: List[ExcludedFile],
+    seen_role: Optional[Set[str]] = None,
+    seen_global: Optional[Set[str]] = None,
+) -> bool:
+    """Try to capture a symlink into the manifest.
+
+    NOTE: Symlinks are *not* copied into artifacts; we record their link target
+    and materialise them via ansible.builtin.file state=link.
+    """
+
+    if seen_global is not None and abs_path in seen_global:
+        return False
+    if seen_role is not None and abs_path in seen_role:
+        return False
+
+    def _mark_seen() -> None:
+        if seen_role is not None:
+            seen_role.add(abs_path)
+        if seen_global is not None:
+            seen_global.add(abs_path)
+
+    if path_filter.is_excluded(abs_path):
+        excluded_out.append(ExcludedFile(path=abs_path, reason="user_excluded"))
+        _mark_seen()
+        return False
+
+    deny_link = getattr(policy, "deny_reason_link", None)
+    if callable(deny_link):
+        deny = deny_link(abs_path)
+    else:
+        # Fallback: apply deny_reason() but treat "not_regular_file" as acceptable
+        # for symlinks.
+        deny = policy.deny_reason(abs_path)
+        if deny in ("not_regular_file", "not_file", "not_regular"):
+            deny = None
+
+    if deny:
+        excluded_out.append(ExcludedFile(path=abs_path, reason=deny))
+        _mark_seen()
+        return False
+
+    if not os.path.islink(abs_path):
+        excluded_out.append(ExcludedFile(path=abs_path, reason="not_symlink"))
+        _mark_seen()
+        return False
+
+    try:
+        target = os.readlink(abs_path)
+    except OSError:
+        excluded_out.append(ExcludedFile(path=abs_path, reason="unreadable"))
+        _mark_seen()
+        return False
+
+    managed_out.append(ManagedLink(path=abs_path, target=target, reason=reason))
+    _mark_seen()
+    return True
+
+
 def _is_confish(path: str) -> bool:
     base = os.path.basename(path)
     _, ext = os.path.splitext(base)
@@ -408,23 +632,12 @@ _SYSTEM_CAPTURE_GLOBS: List[tuple[str, str]] = [
     # mounts
     ("/etc/fstab", "system_mounts"),
     ("/etc/crypttab", "system_mounts"),
-    # logrotate
-    ("/etc/logrotate.conf", "system_logrotate"),
-    ("/etc/logrotate.d/*", "system_logrotate"),
     # sysctl / modules
     ("/etc/sysctl.conf", "system_sysctl"),
     ("/etc/sysctl.d/*", "system_sysctl"),
     ("/etc/modprobe.d/*", "system_modprobe"),
     ("/etc/modules", "system_modprobe"),
     ("/etc/modules-load.d/*", "system_modprobe"),
-    # cron
-    ("/etc/crontab", "system_cron"),
-    ("/etc/cron.d/*", "system_cron"),
-    ("/etc/anacrontab", "system_cron"),
-    ("/etc/anacron/*", "system_cron"),
-    ("/var/spool/cron/crontabs/*", "system_cron"),
-    ("/var/spool/crontabs/*", "system_cron"),
-    ("/var/spool/cron/*", "system_cron"),
     # network
     ("/etc/netplan/*", "system_network"),
     ("/etc/systemd/network/*", "system_network"),
@@ -680,6 +893,135 @@ def harvest(
     # This avoids multiple Ansible roles managing the same destination file.
     captured_global: Set[str] = set()
 
+    # -------------------------
+    # Cron / logrotate unification
+    #
+    # If cron/logrotate are installed, capture all related configuration/state into
+    # dedicated package roles ("cron" and "logrotate") so the same destination path
+    # is never managed by unrelated roles.
+    #
+    # This includes user-specific crontabs under /var/spool, which means the cron role
+    # should be applied after users have been created (handled in manifest ordering).
+    # -------------------------
+
+    installed_pkgs = backend.installed_packages() or {}
+    installed_names: Set[str] = set(installed_pkgs.keys())
+
+    def _pick_installed(cands: List[str]) -> Optional[str]:
+        for c in cands:
+            if c in installed_names:
+                return c
+        return None
+
+    cron_pkg = _pick_installed(
+        ["cron", "cronie", "cronie-anacron", "vixie-cron", "fcron"]
+    )
+    logrotate_pkg = _pick_installed(["logrotate"])
+
+    cron_role_name = "cron"
+    logrotate_role_name = "logrotate"
+
+    def _is_cron_path(p: str) -> bool:
+        return (
+            p == "/etc/crontab"
+            or p == "/etc/anacrontab"
+            or p in ("/etc/cron.allow", "/etc/cron.deny")
+            or p.startswith("/etc/cron.")
+            or p.startswith("/etc/cron.d/")
+            or p.startswith("/etc/anacron/")
+            or p.startswith("/var/spool/cron/")
+            or p.startswith("/var/spool/crontabs/")
+            or p.startswith("/var/spool/anacron/")
+        )
+
+    def _is_logrotate_path(p: str) -> bool:
+        return p == "/etc/logrotate.conf" or p.startswith("/etc/logrotate.d/")
+
+    cron_snapshot: Optional[PackageSnapshot] = None
+    logrotate_snapshot: Optional[PackageSnapshot] = None
+
+    if cron_pkg:
+        cron_managed: List[ManagedFile] = []
+        cron_excluded: List[ExcludedFile] = []
+        cron_notes: List[str] = []
+        cron_seen: Set[str] = set()
+
+        cron_globs = [
+            "/etc/crontab",
+            "/etc/cron.d/*",
+            "/etc/cron.hourly/*",
+            "/etc/cron.daily/*",
+            "/etc/cron.weekly/*",
+            "/etc/cron.monthly/*",
+            "/etc/cron.allow",
+            "/etc/cron.deny",
+            "/etc/anacrontab",
+            "/etc/anacron/*",
+            # user crontabs / spool state
+            "/var/spool/cron/*",
+            "/var/spool/cron/crontabs/*",
+            "/var/spool/crontabs/*",
+            "/var/spool/anacron/*",
+        ]
+        for spec in cron_globs:
+            for path in _iter_matching_files(spec):
+                if not os.path.isfile(path) or os.path.islink(path):
+                    continue
+                _capture_file(
+                    bundle_dir=bundle_dir,
+                    role_name=cron_role_name,
+                    abs_path=path,
+                    reason="system_cron",
+                    policy=policy,
+                    path_filter=path_filter,
+                    managed_out=cron_managed,
+                    excluded_out=cron_excluded,
+                    seen_role=cron_seen,
+                    seen_global=captured_global,
+                )
+
+        cron_snapshot = PackageSnapshot(
+            package=cron_pkg,
+            role_name=cron_role_name,
+            managed_files=cron_managed,
+            excluded=cron_excluded,
+            notes=cron_notes,
+        )
+
+    if logrotate_pkg:
+        lr_managed: List[ManagedFile] = []
+        lr_excluded: List[ExcludedFile] = []
+        lr_notes: List[str] = []
+        lr_seen: Set[str] = set()
+
+        lr_globs = [
+            "/etc/logrotate.conf",
+            "/etc/logrotate.d/*",
+        ]
+        for spec in lr_globs:
+            for path in _iter_matching_files(spec):
+                if not os.path.isfile(path) or os.path.islink(path):
+                    continue
+                _capture_file(
+                    bundle_dir=bundle_dir,
+                    role_name=logrotate_role_name,
+                    abs_path=path,
+                    reason="system_logrotate",
+                    policy=policy,
+                    path_filter=path_filter,
+                    managed_out=lr_managed,
+                    excluded_out=lr_excluded,
+                    seen_role=lr_seen,
+                    seen_global=captured_global,
+                )
+
+        logrotate_snapshot = PackageSnapshot(
+            package=logrotate_pkg,
+            role_name=logrotate_role_name,
+            managed_files=lr_managed,
+            excluded=lr_excluded,
+            notes=lr_notes,
+        )
     # -------------------------
     # Service roles
     # -------------------------
@@ -695,6 +1037,17 @@ def harvest(
     excluded_by_role: Dict[str, List[ExcludedFile]] = {}
 
     enabled_services = list_enabled_services()
+
+    # Avoid role-name collisions with dedicated cron/logrotate package roles.
+    if cron_snapshot is not None or logrotate_snapshot is not None:
+        blocked_roles = set()
+        if cron_snapshot is not None:
+            blocked_roles.add(cron_role_name)
+        if logrotate_snapshot is not None:
+            blocked_roles.add(logrotate_role_name)
+        enabled_services = [
+            u for u in enabled_services if _role_name_from_unit(u) not in blocked_roles
+        ]
     enabled_set = set(enabled_services)
 
     def _service_sort_key(unit: str) -> tuple[int, str, str]:
@@ -804,6 +1157,10 @@ def harvest(
             for path, reason in backend.modified_paths(pkg, etc_paths).items():
                 if not os.path.isfile(path) or os.path.islink(path):
                     continue
+                if cron_snapshot is not None and _is_cron_path(path):
+                    continue
+                if logrotate_snapshot is not None and _is_logrotate_path(path):
+                    continue
                 if backend.is_pkg_config_path(path):
                     continue
                 candidates.setdefault(path, reason)
@@ -992,7 +1349,20 @@ def harvest(
     manual_pkgs_skipped: List[str] = []
     pkg_snaps: List[PackageSnapshot] = []
 
+    # Add dedicated cron/logrotate roles (if detected) as package roles.
+    # These roles centralise all cron/logrotate managed files so they aren't scattered
+    # across unrelated roles.
+    if cron_snapshot is not None:
+        pkg_snaps.append(cron_snapshot)
+    if logrotate_snapshot is not None:
+        pkg_snaps.append(logrotate_snapshot)
     for pkg in sorted(manual_pkgs):
+        if cron_snapshot is not None and pkg == cron_pkg:
+            manual_pkgs_skipped.append(pkg)
+            continue
+        if logrotate_snapshot is not None and pkg == logrotate_pkg:
+            manual_pkgs_skipped.append(pkg)
+            continue
         if pkg in covered_by_services:
             manual_pkgs_skipped.append(pkg)
             continue
@@ -1009,6 +1379,10 @@ def harvest(
         for path, reason in backend.modified_paths(pkg, etc_paths).items():
             if not os.path.isfile(path) or os.path.islink(path):
                 continue
+            if cron_snapshot is not None and _is_cron_path(path):
+                continue
+            if logrotate_snapshot is not None and _is_logrotate_path(path):
+                continue
             if backend.is_pkg_config_path(path):
                 continue
             candidates.setdefault(path, reason)
@@ -1065,11 +1439,72 @@ def harvest(
                 package=pkg,
                 role_name=role,
                 managed_files=managed,
+                managed_links=[],
                 excluded=excluded,
                 notes=notes,
             )
         )
 
+    # -------------------------
+    # Web server enablement symlinks (nginx/apache2)
+    #
+    # Debian-style nginx/apache2 configurations often use *-enabled directories
+    # populated with symlinks pointing back into *-available. The symlinks
+    # represent the enablement state and are important to reproduce.
+    #
+    # We only harvest these when the relevant service/package has already been
+    # detected in this run (i.e. we have a role that will manage nginx/apache2).
+    # -------------------------
+
+    def _find_role_snapshot(role_name: str):
+        for s in service_snaps:
+            if s.role_name == role_name:
+                return s
+        for p in pkg_snaps:
+            if p.role_name == role_name:
+                return p
+        return None
+
+    def _capture_enabled_symlinks(role_name: str, dirs: List[str]) -> None:
+        snap = _find_role_snapshot(role_name)
+        if snap is None:
+            return
+
+        role_seen = seen_by_role.setdefault(role_name, set())
+        for d in dirs:
+            if not os.path.isdir(d):
+                continue
+            for pth in sorted(glob.glob(os.path.join(d, "*"))):
+                if not os.path.islink(pth):
+                    continue
+                _capture_link(
+                    role_name=role_name,
+                    abs_path=pth,
+                    reason="enabled_symlink",
+                    policy=policy,
+                    path_filter=path_filter,
+                    managed_out=snap.managed_links,
+                    excluded_out=snap.excluded,
+                    seen_role=role_seen,
+                    seen_global=captured_global,
+                )
+
+    _capture_enabled_symlinks(
+        "nginx",
+        [
+            "/etc/nginx/modules-enabled",
+            "/etc/nginx/sites-enabled",
+        ],
+    )
+    _capture_enabled_symlinks(
+        "apache2",
+        [
+            "/etc/apache2/conf-enabled",
+            "/etc/apache2/mods-enabled",
+            "/etc/apache2/sites-enabled",
+        ],
+    )
+
     # -------------------------
     # Users role (non-system users)
     # -------------------------
@@ -1087,6 +1522,18 @@ def harvest(
     users_role_name = "users"
     users_role_seen = seen_by_role.setdefault(users_role_name, set())
 
+    skel_dir = "/etc/skel"
+    # Dotfiles to harvest for non-system users. For the common "skeleton"
+    # files, only capture if the user's copy differs from /etc/skel.
+    skel_dotfiles = [
+        (".bashrc", "user_shell_rc"),
+        (".profile", "user_profile"),
+        (".bash_logout", "user_shell_logout"),
+    ]
+    extra_dotfiles = [
+        (".bash_aliases", "user_shell_aliases"),
+    ]
+
     for u in user_records:
         users_list.append(
             {
@@ -1121,6 +1568,48 @@ def harvest(
                 seen_global=captured_global,
             )
 
+        # Capture common per-user shell dotfiles when they differ from /etc/skel.
+        # These still go through IgnorePolicy and user path filters.
+        home = (u.home or "").rstrip("/")
+        if home and home.startswith("/"):
+            for rel, reason in skel_dotfiles:
+                upath = os.path.join(home, rel)
+                if not os.path.exists(upath):
+                    continue
+                skel_path = os.path.join(skel_dir, rel)
+                if not _files_differ(upath, skel_path, max_bytes=policy.max_file_bytes):
+                    continue
+                _capture_file(
+                    bundle_dir=bundle_dir,
+                    role_name=users_role_name,
+                    abs_path=upath,
+                    reason=reason,
+                    policy=policy,
+                    path_filter=path_filter,
+                    managed_out=users_managed,
+                    excluded_out=users_excluded,
+                    seen_role=users_role_seen,
+                    seen_global=captured_global,
+                )
+
+            # Capture other common per-user shell files unconditionally if present.
+            for rel, reason in extra_dotfiles:
+                upath = os.path.join(home, rel)
+                if not os.path.exists(upath):
+                    continue
+                _capture_file(
+                    bundle_dir=bundle_dir,
+                    role_name=users_role_name,
+                    abs_path=upath,
+                    reason=reason,
+                    policy=policy,
+                    path_filter=path_filter,
+                    managed_out=users_managed,
+                    excluded_out=users_excluded,
+                    seen_role=users_role_seen,
+                    seen_global=captured_global,
+                )
+
     users_snapshot = UsersSnapshot(
         role_name=users_role_name,
         users=users_list,
@@ -1484,12 +1973,85 @@ def harvest(
     extra_notes: List[str] = []
     extra_excluded: List[ExcludedFile] = []
     extra_managed: List[ManagedFile] = []
+    extra_managed_dirs: List[ManagedDir] = []
+    extra_dir_seen: Set[str] = set()
+
+    def _walk_and_capture_dirs(root: str) -> None:
+        root = os.path.normpath(root)
+        if not root.startswith("/"):
+            root = "/" + root
+        if not os.path.isdir(root) or os.path.islink(root):
+            return
+        for dirpath, dirnames, _ in os.walk(root, followlinks=False):
+            if len(extra_managed_dirs) >= MAX_FILES_CAP:
+                extra_notes.append(
+                    f"Reached directory cap ({MAX_FILES_CAP}) while scanning {root}."
+                )
+                return
+            dirpath = os.path.normpath(dirpath)
+            if not dirpath.startswith("/"):
+                dirpath = "/" + dirpath
+            if path_filter.is_excluded(dirpath):
+                # Prune excluded subtrees.
+                dirnames[:] = []
+                continue
+            if os.path.islink(dirpath) or not os.path.isdir(dirpath):
+                dirnames[:] = []
+                continue
+
+            if dirpath not in extra_dir_seen:
+                deny = None
+                deny_dir = getattr(policy, "deny_reason_dir", None)
+                if callable(deny_dir):
+                    deny = deny_dir(dirpath)
+                else:
+                    deny = policy.deny_reason(dirpath)
+                    if deny in ("not_regular_file", "not_file", "not_regular"):
+                        deny = None
+                if not deny:
+                    try:
+                        owner, group, mode = stat_triplet(dirpath)
+                        extra_managed_dirs.append(
+                            ManagedDir(
+                                path=dirpath,
+                                owner=owner,
+                                group=group,
+                                mode=mode,
+                                reason="user_include_dir",
+                            )
+                        )
+                    except OSError:
+                        pass
+                extra_dir_seen.add(dirpath)
+
+            # Prune excluded dirs and symlinks early.
+            pruned: List[str] = []
+            for d in dirnames:
+                p = os.path.join(dirpath, d)
+                if os.path.islink(p) or path_filter.is_excluded(p):
+                    continue
+                pruned.append(d)
+            dirnames[:] = pruned
+
     extra_role_name = "extra_paths"
     extra_role_seen = seen_by_role.setdefault(extra_role_name, set())
 
     include_specs = list(include_paths or [])
     exclude_specs = list(exclude_paths or [])
 
+    # If any include pattern points at a directory, capture that directory tree's
+    # ownership/mode so the manifest can recreate it accurately.
+    include_pats = path_filter.iter_include_patterns()
+    for pat in include_pats:
+        if pat.kind == "prefix":
+            p = pat.value
+            if os.path.isdir(p) and not os.path.islink(p):
+                _walk_and_capture_dirs(p)
+        elif pat.kind == "glob":
+            for h in glob.glob(pat.value, recursive=True):
+                if os.path.isdir(h) and not os.path.islink(h):
+                    _walk_and_capture_dirs(h)
+
     if include_specs:
         extra_notes.append("User include patterns:")
         extra_notes.extend([f"- {p}" for p in include_specs])
@@ -1529,6 +2091,7 @@ def harvest(
         role_name=extra_role_name,
         include_patterns=include_specs,
         exclude_patterns=exclude_specs,
+        managed_dirs=extra_managed_dirs,
         managed_files=extra_managed,
         excluded=extra_excluded,
         notes=extra_notes,
@@ -1537,7 +2100,7 @@ def harvest(
     # -------------------------
     # Inventory: packages (SBOM-ish)
     # -------------------------
-    installed = backend.installed_packages() or {}
+    installed = installed_pkgs
 
     manual_set: Set[str] = set(manual_pkgs or [])
 
@@ -1584,6 +2147,58 @@ def harvest(
             "roles": roles,
         }
 
+    # Ensure every role has explicit managed_dirs for parent directories of managed files.
+    # This lets the manifest create directories with owner/group/mode (ansible-lint friendly)
+    # without a separate "mkdir without perms" task.
+    users_snapshot.managed_dirs = _merge_parent_dirs(
+        users_snapshot.managed_dirs, users_snapshot.managed_files, policy=policy
+    )
+    for s in service_snaps:
+        s.managed_dirs = _merge_parent_dirs(
+            s.managed_dirs,
+            s.managed_files,
+            policy=policy,
+            extra_paths=[ml.path for ml in (s.managed_links or [])],
+        )
+    for p in pkg_snaps:
+        p.managed_dirs = _merge_parent_dirs(
+            p.managed_dirs,
+            p.managed_files,
+            policy=policy,
+            extra_paths=[ml.path for ml in (p.managed_links or [])],
+        )
+
+    if apt_config_snapshot:
+        apt_config_snapshot.managed_dirs = _merge_parent_dirs(
+            apt_config_snapshot.managed_dirs,
+            apt_config_snapshot.managed_files,
+            policy=policy,
+        )
+    if dnf_config_snapshot:
+        dnf_config_snapshot.managed_dirs = _merge_parent_dirs(
+            dnf_config_snapshot.managed_dirs,
+            dnf_config_snapshot.managed_files,
+            policy=policy,
+        )
+    if etc_custom_snapshot:
+        etc_custom_snapshot.managed_dirs = _merge_parent_dirs(
+            etc_custom_snapshot.managed_dirs,
+            etc_custom_snapshot.managed_files,
+            policy=policy,
+        )
+    if usr_local_custom_snapshot:
+        usr_local_custom_snapshot.managed_dirs = _merge_parent_dirs(
+            usr_local_custom_snapshot.managed_dirs,
+            usr_local_custom_snapshot.managed_files,
+            policy=policy,
+        )
+    if extra_paths_snapshot:
+        extra_paths_snapshot.managed_dirs = _merge_parent_dirs(
+            extra_paths_snapshot.managed_dirs,
+            extra_paths_snapshot.managed_files,
+            policy=policy,
+        )
+
     state = {
         "enroll": {
             "version": get_enroll_version(),

enroll/ignore.py

@@ -100,6 +100,12 @@ class IgnorePolicy:
         # Always ignore plain *.log files (rarely useful as config, often noisy).
         if path.endswith(".log"):
             return "log_file"
+        # Ignore editor/backup files that end with a trailing tilde.
+        if path.endswith("~"):
+            return "backup_file"
+        # Ignore backup shadow files
+        if path.startswith("/etc/") and path.endswith("-"):
+            return "backup_file"
 
         if not self.dangerous:
             for g in self.deny_globs or []:
@@ -137,3 +143,75 @@ class IgnorePolicy:
                         return "sensitive_content"
 
         return None
+
+    def deny_reason_dir(self, path: str) -> Optional[str]:
+        """Directory-specific deny logic.
+
+        deny_reason() is file-oriented (it rejects directories as "not_regular_file").
+        For directory metadata capture (so roles can recreate directory trees), we need
+        a lighter-weight check:
+          - apply deny_globs (unless dangerous)
+          - require the path to be a real directory (no symlink)
+          - ensure it's stat'able/readable
+
+        No size checks or content scanning are performed for directories.
+        """
+        if not self.dangerous:
+            for g in self.deny_globs or []:
+                if fnmatch.fnmatch(path, g):
+                    return "denied_path"
+
+        try:
+            os.stat(path, follow_symlinks=True)
+        except OSError:
+            return "unreadable"
+
+        if os.path.islink(path):
+            return "symlink"
+
+        if not os.path.isdir(path):
+            return "not_directory"
+
+        return None
+
+    def deny_reason_link(self, path: str) -> Optional[str]:
+        """Symlink-specific deny logic.
+
+        Symlinks are meaningful configuration state (e.g. Debian-style
+        *-enabled directories). deny_reason() is file-oriented and rejects
+        symlinks as "not_regular_file".
+
+        For symlinks we:
+          - apply the usual deny_globs (unless dangerous)
+          - ensure the path is a symlink and we can readlink() it
+
+        No size checks or content scanning are performed for symlinks.
+        """
+
+        # Keep the same fast-path filename ignores as deny_reason().
+        if path.endswith(".log"):
+            return "log_file"
+        if path.endswith("~"):
+            return "backup_file"
+        if path.startswith("/etc/") and path.endswith("-"):
+            return "backup_file"
+
+        if not self.dangerous:
+            for g in self.deny_globs or []:
+                if fnmatch.fnmatch(path, g):
+                    return "denied_path"
+
+        try:
+            os.lstat(path)
+        except OSError:
+            return "unreadable"
+
+        if not os.path.islink(path):
+            return "not_symlink"
+
+        try:
+            os.readlink(path)
+        except OSError:
+            return "unreadable"
+
+        return None

enroll/jinjaturtle.py

@@ -8,7 +8,45 @@ from pathlib import Path
 from typing import Optional
 
 
-SUPPORTED_EXTS = {".ini", ".json", ".toml", ".yaml", ".yml", ".xml"}
+SYSTEMD_SUFFIXES = {
+    ".service",
+    ".socket",
+    ".target",
+    ".timer",
+    ".path",
+    ".mount",
+    ".automount",
+    ".slice",
+    ".swap",
+    ".scope",
+    ".link",
+    ".netdev",
+    ".network",
+}
+
+SUPPORTED_SUFFIXES = {
+    ".ini",
+    ".cfg",
+    ".json",
+    ".toml",
+    ".yaml",
+    ".yml",
+    ".xml",
+    ".repo",
+} | SYSTEMD_SUFFIXES
+
+
+def infer_other_formats(dest_path: str) -> Optional[str]:
+    p = Path(dest_path)
+    name = p.name.lower()
+    suffix = p.suffix.lower()
+    # postfix
+    if name == "main.cf":
+        return "postfix"
+    # systemd units
+    if suffix in SYSTEMD_SUFFIXES:
+        return "systemd"
+    return None
 
 
 @dataclass(frozen=True)
@@ -22,9 +60,15 @@ def find_jinjaturtle_cmd() -> Optional[str]:
     return shutil.which("jinjaturtle")
 
 
-def can_jinjify_path(path: str) -> bool:
-    p = Path(path)
-    return p.suffix.lower() in SUPPORTED_EXTS
+def can_jinjify_path(dest_path: str) -> bool:
+    p = Path(dest_path)
+    suffix = p.suffix.lower()
+    if infer_other_formats(dest_path):
+        return True
+    # allow unambiguous structured formats
+    if suffix in SUPPORTED_SUFFIXES:
+        return True
+    return False
 
 
 def run_jinjaturtle(

enroll/manifest.py

@@ -11,8 +11,9 @@ from pathlib import Path
 from typing import Any, Dict, List, Optional, Set, Tuple
 
 from .jinjaturtle import (
-    find_jinjaturtle_cmd,
     can_jinjify_path,
+    find_jinjaturtle_cmd,
+    infer_other_formats,
     run_jinjaturtle,
 )
 
@@ -162,6 +163,19 @@ def _write_role_scaffold(role_dir: str) -> None:
     os.makedirs(os.path.join(role_dir, "templates"), exist_ok=True)
 
 
+def _role_tag(role: str) -> str:
+    """Return a stable Ansible tag name for a role.
+
+    Used by `enroll diff --enforce` to run only the roles needed to repair drift.
+    """
+    r = str(role or "").strip()
+    # Ansible tag charset is fairly permissive, but keep it portable and consistent.
+    safe = re.sub(r"[^A-Za-z0-9_-]+", "_", r).strip("_")
+    if not safe:
+        safe = "other"
+    return f"role_{safe}"
+
+
 def _write_playbook_all(path: str, roles: List[str]) -> None:
     pb_lines = [
         "---",
@@ -172,7 +186,8 @@ def _write_playbook_all(path: str, roles: List[str]) -> None:
         "  roles:",
     ]
     for r in roles:
-        pb_lines.append(f"    - {r}")
+        pb_lines.append(f"    - role: {r}")
+        pb_lines.append(f"      tags: [{_role_tag(r)}]")
     with open(path, "w", encoding="utf-8") as f:
         f.write("\n".join(pb_lines) + "\n")
 
@@ -187,7 +202,8 @@ def _write_playbook_host(path: str, fqdn: str, roles: List[str]) -> None:
         "  roles:",
     ]
     for r in roles:
-        pb_lines.append(f"    - {r}")
+        pb_lines.append(f"    - role: {r}")
+        pb_lines.append(f"      tags: [{_role_tag(r)}]")
     with open(path, "w", encoding="utf-8") as f:
         f.write("\n".join(pb_lines) + "\n")
 
@@ -309,7 +325,10 @@ def _jinjify_managed_files(
             continue
 
         try:
-            res = run_jinjaturtle(jt_exe, artifact_path, role_name=role)
+            force_fmt = infer_other_formats(dest_path)
+            res = run_jinjaturtle(
+                jt_exe, artifact_path, role_name=role, force_format=force_fmt
+            )
         except Exception:
             # If jinjaturtle cannot process a file for any reason, skip silently.
             # (Enroll's core promise is to be optimistic and non-interactive.)
@@ -344,6 +363,29 @@ def _write_role_defaults(role_dir: str, mapping: Dict[str, Any]) -> None:
         f.write(out)
 
 
+def _build_managed_dirs_var(
+    managed_dirs: List[Dict[str, Any]],
+) -> List[Dict[str, Any]]:
+    """Convert enroll managed_dirs into an Ansible-friendly list of dicts.
+
+    Each dict drives a role task loop and is safe across hosts.
+    """
+    out: List[Dict[str, Any]] = []
+    for d in managed_dirs:
+        dest = d.get("path") or ""
+        if not dest:
+            continue
+        out.append(
+            {
+                "dest": dest,
+                "owner": d.get("owner") or "root",
+                "group": d.get("group") or "root",
+                "mode": d.get("mode") or "0755",
+            }
+        )
+    return out
+
+
 def _build_managed_files_var(
     managed_files: List[Dict[str, Any]],
     templated_src_rels: Set[str],
@@ -383,6 +425,20 @@ def _build_managed_files_var(
     return out
 
 
+def _build_managed_links_var(
+    managed_links: List[Dict[str, Any]],
+) -> List[Dict[str, Any]]:
+    """Convert enroll managed_links into an Ansible-friendly list of dicts."""
+    out: List[Dict[str, Any]] = []
+    for ml in managed_links or []:
+        dest = ml.get("path") or ""
+        src = ml.get("target") or ""
+        if not dest or not src:
+            continue
+        out.append({"dest": dest, "src": src})
+    return out
+
+
 def _render_generic_files_tasks(
     var_prefix: str, *, include_restart_notify: bool
 ) -> str:
@@ -390,7 +446,16 @@ def _render_generic_files_tasks(
     # Using first_found makes roles work in both modes:
     # - site-mode: inventory/host_vars/<host>/<role>/.files/...
     # - non-site: roles/<role>/files/...
-    return f"""- name: Deploy any systemd unit files (templates)
+    return f"""- name: Ensure managed directories exist (preserve owner/group/mode)
+  ansible.builtin.file:
+    path: "{{{{ item.dest }}}}"
+    state: directory
+    owner: "{{{{ item.owner }}}}"
+    group: "{{{{ item.group }}}}"
+    mode: "{{{{ item.mode }}}}"
+  loop: "{{{{ {var_prefix}_managed_dirs | default([]) }}}}"
+
+- name: Deploy any systemd unit files (templates)
   ansible.builtin.template:
     src: "{{{{ item.src_rel }}}}.j2"
     dest: "{{{{ item.dest }}}}"
@@ -463,6 +528,14 @@ def _render_generic_files_tasks(
       | selectattr('kind', 'equalto', 'copy')
       | list }}}}
   notify: "{{{{ item.notify | default([]) }}}}"
+
+- name: Ensure managed symlinks exist
+  ansible.builtin.file:
+    src: "{{{{ item.src }}}}"
+    dest: "{{{{ item.dest }}}}"
+    state: link
+    force: true
+  loop: "{{{{ {var_prefix}_managed_links | default([]) }}}}"
 """
 
 
@@ -787,7 +860,12 @@ def _manifest_from_bundle_dir(
                     group = str(u.get("primary_group") or owner)
                     break
 
-            mode = "0600" if mf.get("reason") == "authorized_keys" else "0644"
+            # Prefer the harvested file mode so we preserve any deliberate
+            # permissions (e.g. 0600 for certain dotfiles). For authorized_keys,
+            # enforce 0600 regardless.
+            mode = mf.get("mode") or "0644"
+            if mf.get("reason") == "authorized_keys":
+                mode = "0600"
             ssh_files.append(
                 {
                     "dest": dest,
@@ -945,6 +1023,7 @@ Generated non-system user accounts and SSH public material.
         var_prefix = role
 
         managed_files = apt_config_snapshot.get("managed_files", [])
+        managed_dirs = apt_config_snapshot.get("managed_dirs", []) or []
         excluded = apt_config_snapshot.get("excluded", [])
         notes = apt_config_snapshot.get("notes", [])
 
@@ -981,12 +1060,20 @@ Generated non-system user accounts and SSH public material.
             notify_systemd=None,
         )
 
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
-        vars_map: Dict[str, Any] = {f"{var_prefix}_managed_files": files_var}
+        vars_map: Dict[str, Any] = {
+            f"{var_prefix}_managed_files": files_var,
+            f"{var_prefix}_managed_dirs": dirs_var,
+        }
         vars_map = _merge_mappings_overwrite(vars_map, jt_map)
 
         if site_mode:
-            _write_role_defaults(role_dir, {f"{var_prefix}_managed_files": []})
+            _write_role_defaults(
+                role_dir,
+                {f"{var_prefix}_managed_files": [], f"{var_prefix}_managed_dirs": []},
+            )
             _write_hostvars(out_dir, fqdn or "", role, vars_map)
         else:
             _write_role_defaults(role_dir, vars_map)
@@ -1096,6 +1183,7 @@ APT configuration harvested from the system (sources, pinning, and keyrings).
         var_prefix = role
 
         managed_files = dnf_config_snapshot.get("managed_files", [])
+        managed_dirs = dnf_config_snapshot.get("managed_dirs", []) or []
         excluded = dnf_config_snapshot.get("excluded", [])
         notes = dnf_config_snapshot.get("notes", [])
 
@@ -1131,12 +1219,20 @@ APT configuration harvested from the system (sources, pinning, and keyrings).
             notify_systemd=None,
         )
 
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
-        vars_map: Dict[str, Any] = {f"{var_prefix}_managed_files": files_var}
+        vars_map: Dict[str, Any] = {
+            f"{var_prefix}_managed_files": files_var,
+            f"{var_prefix}_managed_dirs": dirs_var,
+        }
         vars_map = _merge_mappings_overwrite(vars_map, jt_map)
 
         if site_mode:
-            _write_role_defaults(role_dir, {f"{var_prefix}_managed_files": []})
+            _write_role_defaults(
+                role_dir,
+                {f"{var_prefix}_managed_files": [], f"{var_prefix}_managed_dirs": []},
+            )
             _write_hostvars(out_dir, fqdn or "", role, vars_map)
         else:
             _write_role_defaults(role_dir, vars_map)
@@ -1247,6 +1343,7 @@ DNF/YUM configuration harvested from the system (repos, config files, and RPM GP
         var_prefix = role
 
         managed_files = etc_custom_snapshot.get("managed_files", [])
+        managed_dirs = etc_custom_snapshot.get("managed_dirs", []) or []
         excluded = etc_custom_snapshot.get("excluded", [])
         notes = etc_custom_snapshot.get("notes", [])
 
@@ -1283,12 +1380,20 @@ DNF/YUM configuration harvested from the system (repos, config files, and RPM GP
             notify_systemd="Run systemd daemon-reload",
         )
 
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
-        vars_map: Dict[str, Any] = {f"{var_prefix}_managed_files": files_var}
+        vars_map: Dict[str, Any] = {
+            f"{var_prefix}_managed_files": files_var,
+            f"{var_prefix}_managed_dirs": dirs_var,
+        }
         vars_map = _merge_mappings_overwrite(vars_map, jt_map)
 
         if site_mode:
-            _write_role_defaults(role_dir, {f"{var_prefix}_managed_files": []})
+            _write_role_defaults(
+                role_dir,
+                {f"{var_prefix}_managed_files": [], f"{var_prefix}_managed_dirs": []},
+            )
             _write_hostvars(out_dir, fqdn or "", role, vars_map)
         else:
             _write_role_defaults(role_dir, vars_map)
@@ -1357,6 +1462,7 @@ Unowned /etc config files not attributed to packages or services.
         var_prefix = role
 
         managed_files = usr_local_custom_snapshot.get("managed_files", [])
+        managed_dirs = usr_local_custom_snapshot.get("managed_dirs", []) or []
         excluded = usr_local_custom_snapshot.get("excluded", [])
         notes = usr_local_custom_snapshot.get("notes", [])
 
@@ -1393,12 +1499,20 @@ Unowned /etc config files not attributed to packages or services.
             notify_systemd=None,
         )
 
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
-        vars_map: Dict[str, Any] = {f"{var_prefix}_managed_files": files_var}
+        vars_map: Dict[str, Any] = {
+            f"{var_prefix}_managed_files": files_var,
+            f"{var_prefix}_managed_dirs": dirs_var,
+        }
         vars_map = _merge_mappings_overwrite(vars_map, jt_map)
 
         if site_mode:
-            _write_role_defaults(role_dir, {f"{var_prefix}_managed_files": []})
+            _write_role_defaults(
+                role_dir,
+                {f"{var_prefix}_managed_files": [], f"{var_prefix}_managed_dirs": []},
+            )
             _write_hostvars(out_dir, fqdn or "", role, vars_map)
         else:
             _write_role_defaults(role_dir, vars_map)
@@ -1444,13 +1558,17 @@ Unowned /etc config files not attributed to packages or services.
     # -------------------------
     # extra_paths role (user-requested includes)
     # -------------------------
-    if extra_paths_snapshot and extra_paths_snapshot.get("managed_files"):
+    if extra_paths_snapshot and (
+        extra_paths_snapshot.get("managed_files")
+        or extra_paths_snapshot.get("managed_dirs")
+    ):
         role = extra_paths_snapshot.get("role_name", "extra_paths")
         role_dir = os.path.join(roles_root, role)
         _write_role_scaffold(role_dir)
 
         var_prefix = role
 
+        managed_dirs = extra_paths_snapshot.get("managed_dirs", []) or []
         managed_files = extra_paths_snapshot.get("managed_files", [])
         excluded = extra_paths_snapshot.get("excluded", [])
         notes = extra_paths_snapshot.get("notes", [])
@@ -1489,12 +1607,23 @@ Unowned /etc config files not attributed to packages or services.
             notify_systemd=None,
         )
 
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
-        vars_map: Dict[str, Any] = {f"{var_prefix}_managed_files": files_var}
+        vars_map: Dict[str, Any] = {
+            f"{var_prefix}_managed_dirs": dirs_var,
+            f"{var_prefix}_managed_files": files_var,
+        }
         vars_map = _merge_mappings_overwrite(vars_map, jt_map)
 
         if site_mode:
-            _write_role_defaults(role_dir, {f"{var_prefix}_managed_files": []})
+            _write_role_defaults(
+                role_dir,
+                {
+                    f"{var_prefix}_managed_dirs": [],
+                    f"{var_prefix}_managed_files": [],
+                },
+            )
             _write_hostvars(out_dir, fqdn or "", role, vars_map)
         else:
             _write_role_defaults(role_dir, vars_map)
@@ -1530,6 +1659,10 @@ User-requested extra file harvesting.
 """
             + ("\n".join([f"- {p}" for p in exclude_pats]) or "- (none)")
             + """\n
+## Managed directories
+"""
+            + ("\n".join([f"- {d.get('path')}" for d in managed_dirs]) or "- (none)")
+            + """\n
 ## Managed files
 """
             + ("\n".join([f"- {mf.get('path')}" for mf in managed_files]) or "- (none)")
@@ -1551,8 +1684,6 @@ User-requested extra file harvesting.
 
         manifested_extra_paths_roles.append(role)
 
-        manifested_usr_local_custom_roles.append(role)
-
     # -------------------------
     # Service roles
     # -------------------------
@@ -1561,6 +1692,8 @@ User-requested extra file harvesting.
         unit = svc["unit"]
         pkgs = svc.get("packages", []) or []
         managed_files = svc.get("managed_files", []) or []
+        managed_dirs = svc.get("managed_dirs", []) or []
+        managed_links = svc.get("managed_links", []) or []
 
         role_dir = os.path.join(roles_root, role)
         _write_role_scaffold(role_dir)
@@ -1605,11 +1738,17 @@ User-requested extra file harvesting.
             notify_systemd="Run systemd daemon-reload",
         )
 
+        links_var = _build_managed_links_var(managed_links)
+
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
         base_vars: Dict[str, Any] = {
             f"{var_prefix}_unit_name": unit,
             f"{var_prefix}_packages": pkgs,
             f"{var_prefix}_managed_files": files_var,
+            f"{var_prefix}_managed_dirs": dirs_var,
+            f"{var_prefix}_managed_links": links_var,
             f"{var_prefix}_manage_unit": True,
             f"{var_prefix}_systemd_enabled": bool(enabled_at_harvest),
             f"{var_prefix}_systemd_state": desired_state,
@@ -1624,6 +1763,8 @@ User-requested extra file harvesting.
                     f"{var_prefix}_unit_name": unit,
                     f"{var_prefix}_packages": [],
                     f"{var_prefix}_managed_files": [],
+                    f"{var_prefix}_managed_dirs": [],
+                    f"{var_prefix}_managed_links": [],
                     f"{var_prefix}_manage_unit": False,
                     f"{var_prefix}_systemd_enabled": False,
                     f"{var_prefix}_systemd_state": "stopped",
@@ -1709,6 +1850,9 @@ Generated from `{unit}`.
 ## Managed files
 {os.linesep.join("- " + mf["path"] + " (" + mf["reason"] + ")" for mf in managed_files) or "- (none)"}
 
+## Managed symlinks
+{os.linesep.join("- " + ml["path"] + " -> " + ml["target"] + " (" + ml.get("reason", "") + ")" for ml in managed_links) or "- (none)"}
+
 ## Excluded (possible secrets / unsafe)
 {os.linesep.join("- " + e["path"] + " (" + e["reason"] + ")" for e in excluded) or "- (none)"}
 
@@ -1727,6 +1871,8 @@ Generated from `{unit}`.
         role = pr["role_name"]
         pkg = pr.get("package") or ""
         managed_files = pr.get("managed_files", []) or []
+        managed_dirs = pr.get("managed_dirs", []) or []
+        managed_links = pr.get("managed_links", []) or []
 
         role_dir = os.path.join(roles_root, role)
         _write_role_scaffold(role_dir)
@@ -1768,10 +1914,16 @@ Generated from `{unit}`.
             notify_systemd="Run systemd daemon-reload",
         )
 
+        links_var = _build_managed_links_var(managed_links)
+
+        dirs_var = _build_managed_dirs_var(managed_dirs)
+
         jt_map = _yaml_load_mapping(jt_vars) if jt_vars.strip() else {}
         base_vars: Dict[str, Any] = {
             f"{var_prefix}_packages": pkgs,
             f"{var_prefix}_managed_files": files_var,
+            f"{var_prefix}_managed_dirs": dirs_var,
+            f"{var_prefix}_managed_links": links_var,
         }
         base_vars = _merge_mappings_overwrite(base_vars, jt_map)
 
@@ -1781,6 +1933,8 @@ Generated from `{unit}`.
                 {
                     f"{var_prefix}_packages": [],
                     f"{var_prefix}_managed_files": [],
+                    f"{var_prefix}_managed_dirs": [],
+                    f"{var_prefix}_managed_links": [],
                 },
             )
             _write_hostvars(out_dir, fqdn or "", role, base_vars)
@@ -1823,6 +1977,9 @@ Generated for package `{pkg}`.
 ## Managed files
 {os.linesep.join("- " + mf["path"] + " (" + mf["reason"] + ")" for mf in managed_files) or "- (none)"}
 
+## Managed symlinks
+{os.linesep.join("- " + ml["path"] + " -> " + ml["target"] + " (" + ml.get("reason", "") + ")" for ml in managed_links) or "- (none)"}
+
 ## Excluded (possible secrets / unsafe)
 {os.linesep.join("- " + e["path"] + " (" + e["reason"] + ")" for e in excluded) or "- (none)"}
 
@@ -1835,15 +1992,26 @@ Generated for package `{pkg}`.
             f.write(readme)
 
         manifested_pkg_roles.append(role)
+    # Place cron/logrotate at the end of the playbook so:
+    #   - users exist before we restore per-user crontabs in /var/spool
+    #   - most packages/services are installed/configured first
+    tail_roles: List[str] = []
+    for r in ("cron", "logrotate"):
+        if r in manifested_pkg_roles:
+            tail_roles.append(r)
+
+    main_pkg_roles = [r for r in manifested_pkg_roles if r not in set(tail_roles)]
+
     all_roles = (
         manifested_apt_config_roles
         + manifested_dnf_config_roles
-        + manifested_pkg_roles
+        + main_pkg_roles
         + manifested_service_roles
         + manifested_etc_custom_roles
         + manifested_usr_local_custom_roles
         + manifested_extra_paths_roles
         + manifested_users_roles
+        + tail_roles
     )
 
     if site_mode:

enroll/remote.py

@@ -1,14 +1,183 @@
 from __future__ import annotations
 
+import getpass
 import os
 import shlex
 import shutil
+import sys
+import time
 import tarfile
 import tempfile
 import zipapp
 from pathlib import Path
 from pathlib import PurePosixPath
-from typing import Optional
+from typing import Optional, Callable, TextIO
+
+
+class RemoteSudoPasswordRequired(RuntimeError):
+    """Raised when sudo requires a password but none was provided."""
+
+
+class RemoteSSHKeyPassphraseRequired(RuntimeError):
+    """Raised when SSH private key decryption needs a passphrase."""
+
+
+def _sudo_password_required(out: str, err: str) -> bool:
+    """Return True if sudo output indicates it needs a password/TTY."""
+    blob = (out + "\n" + err).lower()
+    patterns = (
+        "a password is required",
+        "password is required",
+        "a terminal is required to read the password",
+        "no tty present and no askpass program specified",
+        "must have a tty to run sudo",
+        "sudo: sorry, you must have a tty",
+        "askpass",
+    )
+    return any(p in blob for p in patterns)
+
+
+def _sudo_not_permitted(out: str, err: str) -> bool:
+    """Return True if sudo output indicates the user cannot sudo at all."""
+    blob = (out + "\n" + err).lower()
+    patterns = (
+        "is not in the sudoers file",
+        "not allowed to execute",
+        "may not run sudo",
+        "sorry, user",
+    )
+    return any(p in blob for p in patterns)
+
+
+def _sudo_tty_required(out: str, err: str) -> bool:
+    """Return True if sudo output indicates it requires a TTY (sudoers requiretty)."""
+    blob = (out + "\n" + err).lower()
+    patterns = (
+        "must have a tty",
+        "sorry, you must have a tty",
+        "sudo: sorry, you must have a tty",
+        "must have a tty to run sudo",
+    )
+    return any(p in blob for p in patterns)
+
+
+def _resolve_become_password(
+    ask_become_pass: bool,
+    *,
+    prompt: str = "sudo password: ",
+    getpass_fn: Callable[[str], str] = getpass.getpass,
+) -> Optional[str]:
+    if ask_become_pass:
+        return getpass_fn(prompt)
+    return None
+
+
+def _resolve_ssh_key_passphrase(
+    ask_key_passphrase: bool,
+    *,
+    env_var: Optional[str] = None,
+    prompt: str = "SSH key passphrase: ",
+    getpass_fn: Callable[[str], str] = getpass.getpass,
+) -> Optional[str]:
+    """Resolve SSH private-key passphrase from env and/or prompt.
+
+    Precedence:
+      1) --ssh-key-passphrase-env style input (env_var)
+      2) --ask-key-passphrase style interactive prompt
+      3) None
+    """
+    if env_var:
+        val = os.environ.get(str(env_var))
+        if val is None:
+            raise RuntimeError(
+                "SSH key passphrase environment variable is not set: " f"{env_var}"
+            )
+        return val
+
+    if ask_key_passphrase:
+        return getpass_fn(prompt)
+
+    return None
+
+
+def remote_harvest(
+    *,
+    ask_become_pass: bool = False,
+    ask_key_passphrase: bool = False,
+    ssh_key_passphrase_env: Optional[str] = None,
+    no_sudo: bool = False,
+    prompt: str = "sudo password: ",
+    key_prompt: str = "SSH key passphrase: ",
+    getpass_fn: Optional[Callable[[str], str]] = None,
+    stdin: Optional[TextIO] = None,
+    **kwargs,
+):
+    """Call _remote_harvest, with a safe sudo password fallback.
+
+    Behavior:
+      - Run without a password unless --ask-become-pass is set.
+      - If the remote sudo policy requires a password and none was provided,
+        prompt and retry when running interactively.
+    """
+
+    # Resolve defaults at call time (easier to test/monkeypatch, and avoids capturing
+    # sys.stdin / getpass.getpass at import time).
+    if getpass_fn is None:
+        getpass_fn = getpass.getpass
+    if stdin is None:
+        stdin = sys.stdin
+
+    sudo_password = _resolve_become_password(
+        ask_become_pass and not no_sudo,
+        prompt=prompt,
+        getpass_fn=getpass_fn,
+    )
+    ssh_key_passphrase = _resolve_ssh_key_passphrase(
+        ask_key_passphrase,
+        env_var=ssh_key_passphrase_env,
+        prompt=key_prompt,
+        getpass_fn=getpass_fn,
+    )
+
+    while True:
+        try:
+            return _remote_harvest(
+                sudo_password=sudo_password,
+                no_sudo=no_sudo,
+                ssh_key_passphrase=ssh_key_passphrase,
+                **kwargs,
+            )
+        except RemoteSSHKeyPassphraseRequired:
+            # Already tried a passphrase and still failed.
+            if ssh_key_passphrase is not None:
+                raise RemoteSSHKeyPassphraseRequired(
+                    "SSH private key could not be decrypted with the supplied "
+                    "passphrase."
+                ) from None
+
+            # Fallback prompt if interactive.
+            if stdin is not None and getattr(stdin, "isatty", lambda: False)():
+                ssh_key_passphrase = getpass_fn(key_prompt)
+                continue
+
+            raise RemoteSSHKeyPassphraseRequired(
+                "SSH private key is encrypted and needs a passphrase. "
+                "Re-run with --ask-key-passphrase or "
+                "--ssh-key-passphrase-env VAR."
+            )
+
+        except RemoteSudoPasswordRequired:
+            if sudo_password is not None:
+                raise
+
+            # Fallback prompt if interactive.
+            if stdin is not None and getattr(stdin, "isatty", lambda: False)():
+                sudo_password = getpass_fn(prompt)
+                continue
+
+            raise RemoteSudoPasswordRequired(
+                "Remote sudo requires a password. Re-run with --ask-become-pass."
+            )
 
 
 def _safe_extract_tar(tar: tarfile.TarFile, dest: Path) -> None:
@@ -16,7 +185,6 @@ def _safe_extract_tar(tar: tarfile.TarFile, dest: Path) -> None:
 
     Protects against path traversal (e.g. entries containing ../).
     """
-
     # Note: tar member names use POSIX separators regardless of platform.
     dest = dest.resolve()
 
@@ -80,24 +248,162 @@ def _build_enroll_pyz(tmpdir: Path) -> Path:
     return pyz_path
 
 
-def _ssh_run(ssh, cmd: str) -> tuple[int, str, str]:
-    """Run a command over a Paramiko SSHClient."""
-    _stdin, stdout, stderr = ssh.exec_command(cmd)
-    out = stdout.read().decode("utf-8", errors="replace")
-    err = stderr.read().decode("utf-8", errors="replace")
-    rc = stdout.channel.recv_exit_status()
+def _ssh_run(
+    ssh,
+    cmd: str,
+    *,
+    get_pty: bool = False,
+    stdin_text: Optional[str] = None,
+    close_stdin: bool = False,
+) -> tuple[int, str, str]:
+    """Run a command over a Paramiko SSHClient.
+
+    Paramiko's exec_command runs commands without a TTY by default.
+    Some hosts have sudoers "requiretty" enabled, which causes sudo to
+    fail even when passwordless sudo is configured. For those commands,
+    request a PTY.
+
+    We do not request a PTY for commands that stream binary data
+    (e.g. tar/gzip output), as a PTY can corrupt the byte stream.
+    """
+    stdin, stdout, stderr = ssh.exec_command(cmd, get_pty=get_pty)
+    # All three file-like objects share the same underlying Channel.
+    chan = stdout.channel
+
+    if stdin_text is not None and stdin is not None:
+        try:
+            stdin.write(stdin_text)
+            stdin.flush()
+        except Exception:
+            # If the remote side closed stdin early, ignore.
+            pass  # nosec
+        finally:
+            if close_stdin:
+                # For sudo -S, a wrong password causes sudo to re-prompt and wait
+                # forever for more input. We try hard to deliver EOF so sudo can
+                # fail fast.
+                try:
+                    chan.shutdown_write()  # sends EOF to the remote process
+                except Exception:
+                    pass  # nosec
+                try:
+                    stdin.close()
+                except Exception:
+                    pass  # nosec
+
+    # Read incrementally to avoid blocking forever on stdout.read()/stderr.read()
+    # if the remote process is waiting for more input (e.g. sudo password retry).
+    out_chunks: list[bytes] = []
+    err_chunks: list[bytes] = []
+    # Keep a small tail of stderr to detect sudo retry messages without
+    # repeatedly joining potentially large buffers.
+    err_tail = b""
+
+    while True:
+        progressed = False
+        if chan.recv_ready():
+            out_chunks.append(chan.recv(1024 * 64))
+            progressed = True
+        if chan.recv_stderr_ready():
+            chunk = chan.recv_stderr(1024 * 64)
+            err_chunks.append(chunk)
+            err_tail = (err_tail + chunk)[-4096:]
+            progressed = True
+
+        # If we just attempted sudo -S with a single password line and sudo is
+        # asking again, detect it and stop waiting.
+        if close_stdin and stdin_text is not None:
+            blob = err_tail.lower()
+            if b"sorry, try again" in blob or b"incorrect password" in blob:
+                try:
+                    chan.close()
+                except Exception:
+                    pass  # nosec
+                break
+
+        # Exit once the process has exited and we have drained the buffers.
+        if (
+            chan.exit_status_ready()
+            and not chan.recv_ready()
+            and not chan.recv_stderr_ready()
+        ):
+            break
+
+        if not progressed:
+            time.sleep(0.05)
+
+    out = b"".join(out_chunks).decode("utf-8", errors="replace")
+    err = b"".join(err_chunks).decode("utf-8", errors="replace")
+    rc = chan.recv_exit_status() if chan.exit_status_ready() else 1
     return rc, out, err
 
 
-def remote_harvest(
+def _ssh_run_sudo(
+    ssh,
+    cmd: str,
+    *,
+    sudo_password: Optional[str] = None,
+    get_pty: bool = True,
+) -> tuple[int, str, str]:
+    """Run cmd via sudo with a safe non-interactive-first strategy.
+
+    Strategy:
+      1) Try `sudo -n`.
+      2) If sudo reports a password is required and we have one, retry with
+         `sudo -S` and feed it via stdin.
+      3) If sudo reports a password is required and we *don't* have one, raise
+         RemoteSudoPasswordRequired.
+
+    We avoid requesting a PTY unless the remote sudo policy requires it.
+    This makes sudo -S behavior more reliable (wrong passwords fail fast
+    instead of blocking on a PTY).
+    """
+    cmd_n = f"sudo -n -p '' -- {cmd}"
+
+    # First try: never prompt, and prefer no PTY.
+    rc, out, err = _ssh_run(ssh, cmd_n, get_pty=False)
+    need_pty = False
+
+    # Some sudoers configurations require a TTY even for passwordless sudo.
+    if get_pty and rc != 0 and _sudo_tty_required(out, err):
+        need_pty = True
+        rc, out, err = _ssh_run(ssh, cmd_n, get_pty=True)
+
+    if rc == 0:
+        return rc, out, err
+
+    if _sudo_not_permitted(out, err):
+        return rc, out, err
+
+    if _sudo_password_required(out, err):
+        if sudo_password is None:
+            raise RemoteSudoPasswordRequired(
+                "Remote sudo requires a password, but none was provided."
+            )
+        cmd_s = f"sudo -S -p '' -- {cmd}"
+        return _ssh_run(
+            ssh,
+            cmd_s,
+            get_pty=need_pty,
+            stdin_text=str(sudo_password) + "\n",
+            close_stdin=True,
+        )
+
+    return rc, out, err
+
+
+def _remote_harvest(
     *,
     local_out_dir: Path,
     remote_host: str,
-    remote_port: int = 22,
+    remote_port: Optional[int] = None,
     remote_user: Optional[str] = None,
+    remote_ssh_config: Optional[str] = None,
     remote_python: str = "python3",
     dangerous: bool = False,
     no_sudo: bool = False,
+    sudo_password: Optional[str] = None,
+    ssh_key_passphrase: Optional[str] = None,
     include_paths: Optional[list[str]] = None,
     exclude_paths: Optional[list[str]] = None,
 ) -> Path:
@@ -105,7 +411,6 @@ def remote_harvest(
 
     Returns the local path to state.json inside local_out_dir.
     """
-
     try:
         import paramiko  # type: ignore
     except Exception as e:
@@ -133,13 +438,120 @@ def remote_harvest(
         # Users should add the key to known_hosts.
         ssh.set_missing_host_key_policy(paramiko.RejectPolicy())
 
-        ssh.connect(
-            hostname=remote_host,
-            port=int(remote_port),
-            username=remote_user,
-            allow_agent=True,
-            look_for_keys=True,
-        )
+        # Resolve SSH connection parameters.
+        connect_host = remote_host
+        connect_port = int(remote_port) if remote_port is not None else 22
+        connect_user = remote_user
+        key_filename = None
+        sock = None
+        hostkey_name = connect_host
+
+        # Timeouts derived from ssh_config if set (ConnectTimeout).
+        # Used both for socket connect (when we create one) and Paramiko handshake/auth.
+        connect_timeout: Optional[float] = None
+
+        if remote_ssh_config:
+            from paramiko.config import SSHConfig  # type: ignore
+            from paramiko.proxy import ProxyCommand  # type: ignore
+            import socket as _socket
+
+            cfg_path = Path(str(remote_ssh_config)).expanduser()
+            if not cfg_path.exists():
+                raise RuntimeError(f"SSH config file not found: {cfg_path}")
+
+            cfg = SSHConfig()
+            with cfg_path.open("r", encoding="utf-8") as _fp:
+                cfg.parse(_fp)
+            hcfg = cfg.lookup(remote_host)
+
+            connect_host = str(hcfg.get("hostname") or remote_host)
+            hostkey_name = str(hcfg.get("hostkeyalias") or connect_host)
+
+            if remote_port is None and hcfg.get("port"):
+                try:
+                    connect_port = int(str(hcfg.get("port")))
+                except ValueError:
+                    pass
+            if connect_user is None and hcfg.get("user"):
+                connect_user = str(hcfg.get("user"))
+
+            ident = hcfg.get("identityfile")
+            if ident:
+                if isinstance(ident, (list, tuple)):
+                    key_filename = [str(Path(p).expanduser()) for p in ident]
+                else:
+                    key_filename = str(Path(str(ident)).expanduser())
+
+            # Honour OpenSSH ConnectTimeout (seconds) if present.
+            if hcfg.get("connecttimeout"):
+                try:
+                    connect_timeout = float(str(hcfg.get("connecttimeout")))
+                except (TypeError, ValueError):
+                    connect_timeout = None
+
+            proxycmd = hcfg.get("proxycommand")
+
+            # AddressFamily support: inet (IPv4 only), inet6 (IPv6 only), any (default).
+            addrfam = str(hcfg.get("addressfamily") or "any").strip().lower()
+            family: Optional[int] = None
+            if addrfam == "inet":
+                family = _socket.AF_INET
+            elif addrfam == "inet6":
+                family = _socket.AF_INET6
+
+            if proxycmd:
+                # ProxyCommand provides the transport; AddressFamily doesn't apply here.
+                sock = ProxyCommand(str(proxycmd))
+            elif family is not None:
+                # Enforce the requested address family by pre-connecting the socket and
+                # passing it into Paramiko via sock=.
+                last_err: Optional[OSError] = None
+                infos = _socket.getaddrinfo(
+                    connect_host, connect_port, family, _socket.SOCK_STREAM
+                )
+                for af, socktype, proto, _, sa in infos:
+                    s = _socket.socket(af, socktype, proto)
+                    if connect_timeout is not None:
+                        s.settimeout(connect_timeout)
+                    try:
+                        s.connect(sa)
+                        sock = s
+                        break
+                    except OSError as e:
+                        last_err = e
+                        try:
+                            s.close()
+                        except Exception:
+                            pass  # nosec
+                if sock is None and last_err is not None:
+                    raise last_err
+            elif hostkey_name != connect_host:
+                # If HostKeyAlias is used, connect to HostName via a socket but
+                # use HostKeyAlias for known_hosts lookups.
+                sock = _socket.create_connection(
+                    (connect_host, connect_port), timeout=connect_timeout
+                )
+
+        # If we created a socket (sock!=None), pass hostkey_name as hostname so
+        # known_hosts lookup uses HostKeyAlias (or whatever hostkey_name resolved to).
+        try:
+            ssh.connect(
+                hostname=hostkey_name if sock is not None else connect_host,
+                port=connect_port,
+                username=connect_user,
+                key_filename=key_filename,
+                sock=sock,
+                allow_agent=True,
+                look_for_keys=True,
+                timeout=connect_timeout,
+                banner_timeout=connect_timeout,
+                auth_timeout=connect_timeout,
+                passphrase=ssh_key_passphrase,
+            )
+        except paramiko.PasswordRequiredException as e:  # type: ignore[attr-defined]
+            raise RemoteSSHKeyPassphraseRequired(
+                "SSH private key is encrypted and no passphrase was provided."
+            ) from e
 
         # If no username was explicitly provided, SSH may have selected a default.
         # We need a concrete username for the (sudo) chown step below.
@@ -182,34 +594,45 @@ def remote_harvest(
             for p in exclude_paths or []:
                 argv.extend(["--exclude-path", str(p)])
 
-            _cmd = " ".join(shlex.quote(a) for a in argv)
+            _cmd = " ".join(map(shlex.quote, argv))
             if not no_sudo:
+                # Prefer non-interactive sudo first; retry with -S only when needed.
+                rc, out, err = _ssh_run_sudo(
+                    ssh, _cmd, sudo_password=sudo_password, get_pty=True
+                )
                 cmd = f"sudo {_cmd}"
             else:
                 cmd = _cmd
-            rc, out, err = _ssh_run(ssh, cmd)
+                rc, out, err = _ssh_run(ssh, cmd, get_pty=False)
             if rc != 0:
                 raise RuntimeError(
                     "Remote harvest failed.\n"
                     f"Command: {cmd}\n"
                     f"Exit code: {rc}\n"
+                    f"Stdout: {out.strip()}\n"
                     f"Stderr: {err.strip()}"
                 )
 
             if not no_sudo:
-                # Ensure user can read the files, before we tar it
+                # Ensure user can read the files, before we tar it.
                 if not resolved_user:
                     raise RuntimeError(
                         "Unable to determine remote username for chown. "
                         "Pass --remote-user explicitly or use --no-sudo."
                     )
-                cmd = f"sudo chown -R {resolved_user} {rbundle}"
-                rc, out, err = _ssh_run(ssh, cmd)
+                chown_cmd = f"chown -R {resolved_user} {rbundle}"
+                rc, out, err = _ssh_run_sudo(
+                    ssh,
+                    chown_cmd,
+                    sudo_password=sudo_password,
+                    get_pty=True,
+                )
                 if rc != 0:
                     raise RuntimeError(
                         "chown of harvest failed.\n"
-                        f"Command: {cmd}\n"
+                        f"Command: sudo {chown_cmd}\n"
                         f"Exit code: {rc}\n"
+                        f"Stdout: {out.strip()}\n"
                         f"Stderr: {err.strip()}"
                     )
 

enroll/schema/__init__.py

@@ -0,0 +1,4 @@
+"""Vendored JSON schemas.
+
+These are used by `enroll validate` so validation can run offline.
+"""

enroll/schema/state.schema.json

@@ -0,0 +1,712 @@
+{
+  "$defs": {
+    "AptConfigSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "role_name": {
+              "const": "apt_config"
+            }
+          },
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "DnfConfigSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "role_name": {
+              "const": "dnf_config"
+            }
+          },
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "EtcCustomSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "role_name": {
+              "const": "etc_custom"
+            }
+          },
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "ExcludedFile": {
+      "additionalProperties": false,
+      "properties": {
+        "path": {
+          "minLength": 1,
+          "pattern": "^/.*",
+          "type": "string"
+        },
+        "reason": {
+          "enum": [
+            "user_excluded",
+            "unreadable",
+	    "backup_file",
+            "log_file",
+            "denied_path",
+            "too_large",
+            "not_regular_file",
+            "not_symlink",
+            "binary_like",
+            "sensitive_content"
+          ],
+          "type": "string"
+        }
+      },
+      "required": [
+        "path",
+        "reason"
+      ],
+      "type": "object"
+    },
+    "ExtraPathsSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "exclude_patterns": {
+              "items": {
+                "type": "string"
+              },
+              "type": "array"
+            },
+            "include_patterns": {
+              "items": {
+                "type": "string"
+              },
+              "type": "array"
+            },
+            "role_name": {
+              "const": "extra_paths"
+            }
+          },
+          "required": [
+            "include_patterns",
+            "exclude_patterns"
+          ],
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "InstalledPackageInstance": {
+      "additionalProperties": false,
+      "properties": {
+        "arch": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "version": {
+          "minLength": 1,
+          "type": "string"
+        }
+      },
+      "required": [
+        "version",
+        "arch"
+      ],
+      "type": "object"
+    },
+    "ManagedDir": {
+      "additionalProperties": false,
+      "properties": {
+        "group": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "mode": {
+          "pattern": "^[0-7]{4}$",
+          "type": "string"
+        },
+        "owner": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "path": {
+          "minLength": 1,
+          "pattern": "^/.*",
+          "type": "string"
+        },
+        "reason": {
+          "enum": [
+            "parent_of_managed_file",
+            "user_include_dir"
+          ],
+          "type": "string"
+        }
+      },
+      "required": [
+        "path",
+        "owner",
+        "group",
+        "mode",
+        "reason"
+      ],
+      "type": "object"
+    },
+    "ManagedFile": {
+      "additionalProperties": false,
+      "properties": {
+        "group": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "mode": {
+          "pattern": "^[0-7]{4}$",
+          "type": "string"
+        },
+        "owner": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "path": {
+          "minLength": 1,
+          "pattern": "^/.*",
+          "type": "string"
+        },
+        "reason": {
+          "enum": [
+            "apt_config",
+            "apt_keyring",
+            "apt_signed_by_keyring",
+            "apt_source",
+            "authorized_keys",
+            "cron_snippet",
+            "custom_specific_path",
+            "custom_unowned",
+            "dnf_config",
+            "logrotate_snippet",
+            "modified_conffile",
+            "modified_packaged_file",
+            "related_timer",
+            "rpm_gpg_key",
+            "ssh_public_key",
+            "system_cron",
+            "system_firewall",
+            "system_logrotate",
+            "system_modprobe",
+            "system_mounts",
+            "system_network",
+            "system_rc",
+            "system_security",
+            "system_sysctl",
+            "systemd_dropin",
+            "systemd_envfile",
+            "user_include",
+            "user_profile",
+            "user_shell_aliases",
+            "user_shell_logout",
+            "user_shell_rc",
+            "usr_local_bin_script",
+            "usr_local_etc_custom",
+            "yum_conf",
+            "yum_config",
+            "yum_repo"
+          ],
+          "type": "string"
+        },
+        "src_rel": {
+          "minLength": 1,
+          "pattern": "^[^/].*",
+          "type": "string"
+        }
+      },
+      "required": [
+        "path",
+        "src_rel",
+        "owner",
+        "group",
+        "mode",
+        "reason"
+      ],
+      "type": "object"
+    },
+    "ManagedLink": {
+      "additionalProperties": false,
+      "type": "object",
+      "properties": {
+        "path": {
+          "type": "string",
+          "minLength": 1,
+          "pattern": "^/.*"
+        },
+        "target": {
+          "type": "string",
+          "minLength": 1
+        },
+        "reason": {
+          "type": "string",
+          "enum": [
+            "enabled_symlink"
+          ]
+        }
+      },
+      "required": [
+        "path",
+        "target",
+        "reason"
+      ]
+    },
+    "ObservedVia": {
+      "oneOf": [
+        {
+          "additionalProperties": false,
+          "properties": {
+            "kind": {
+              "const": "user_installed"
+            }
+          },
+          "required": [
+            "kind"
+          ],
+          "type": "object"
+        },
+        {
+          "additionalProperties": false,
+          "properties": {
+            "kind": {
+              "const": "systemd_unit"
+            },
+            "ref": {
+              "minLength": 1,
+              "type": "string"
+            }
+          },
+          "required": [
+            "kind",
+            "ref"
+          ],
+          "type": "object"
+        },
+        {
+          "additionalProperties": false,
+          "properties": {
+            "kind": {
+              "const": "package_role"
+            },
+            "ref": {
+              "minLength": 1,
+              "type": "string"
+            }
+          },
+          "required": [
+            "kind",
+            "ref"
+          ],
+          "type": "object"
+        }
+      ]
+    },
+    "PackageInventoryEntry": {
+      "additionalProperties": false,
+      "properties": {
+        "arches": {
+          "items": {
+            "minLength": 1,
+            "type": "string"
+          },
+          "type": "array"
+        },
+        "installations": {
+          "items": {
+            "$ref": "#/$defs/InstalledPackageInstance"
+          },
+          "type": "array"
+        },
+        "observed_via": {
+          "items": {
+            "$ref": "#/$defs/ObservedVia"
+          },
+          "type": "array"
+        },
+        "roles": {
+          "items": {
+            "minLength": 1,
+            "type": "string"
+          },
+          "type": "array"
+        },
+        "version": {
+          "type": [
+            "string",
+            "null"
+          ]
+        }
+      },
+      "required": [
+        "version",
+        "arches",
+        "installations",
+        "observed_via",
+        "roles"
+      ],
+      "type": "object"
+    },
+    "PackageSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "package": {
+              "minLength": 1,
+              "type": "string"
+            }
+          },
+          "required": [
+            "package"
+          ],
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "RoleCommon": {
+      "properties": {
+        "excluded": {
+          "items": {
+            "$ref": "#/$defs/ExcludedFile"
+          },
+          "type": "array"
+        },
+        "managed_dirs": {
+          "items": {
+            "$ref": "#/$defs/ManagedDir"
+          },
+          "type": "array"
+        },
+        "managed_files": {
+          "items": {
+            "$ref": "#/$defs/ManagedFile"
+          },
+          "type": "array"
+        },
+        "managed_links": {
+          "items": {
+            "$ref": "#/$defs/ManagedLink"
+          },
+          "type": "array"
+        },
+        "notes": {
+          "items": {
+            "type": "string"
+          },
+          "type": "array"
+        },
+        "role_name": {
+          "minLength": 1,
+          "pattern": "^[A-Za-z0-9_]+$",
+          "type": "string"
+        }
+      },
+      "required": [
+        "role_name",
+        "managed_dirs",
+        "managed_files",
+        "excluded",
+        "notes"
+      ],
+      "type": "object"
+    },
+    "ServiceSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "active_state": {
+              "type": [
+                "string",
+                "null"
+              ]
+            },
+            "condition_result": {
+              "type": [
+                "string",
+                "null"
+              ]
+            },
+            "packages": {
+              "items": {
+                "minLength": 1,
+                "type": "string"
+              },
+              "type": "array"
+            },
+            "role_name": {
+              "minLength": 1,
+              "pattern": "^[a-z_][a-z0-9_]*$",
+              "type": "string"
+            },
+            "sub_state": {
+              "type": [
+                "string",
+                "null"
+              ]
+            },
+            "unit": {
+              "minLength": 1,
+              "type": "string"
+            },
+            "unit_file_state": {
+              "type": [
+                "string",
+                "null"
+              ]
+            }
+          },
+          "required": [
+            "unit",
+            "packages",
+            "active_state",
+            "sub_state",
+            "unit_file_state",
+            "condition_result"
+          ],
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "UserEntry": {
+      "additionalProperties": false,
+      "properties": {
+        "gecos": {
+          "type": "string"
+        },
+        "gid": {
+          "minimum": 0,
+          "type": "integer"
+        },
+        "home": {
+          "type": "string"
+        },
+        "name": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "primary_group": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "shell": {
+          "type": "string"
+        },
+        "supplementary_groups": {
+          "items": {
+            "minLength": 1,
+            "type": "string"
+          },
+          "type": "array"
+        },
+        "uid": {
+          "minimum": 0,
+          "type": "integer"
+        }
+      },
+      "required": [
+        "name",
+        "uid",
+        "gid",
+        "gecos",
+        "home",
+        "shell",
+        "primary_group",
+        "supplementary_groups"
+      ],
+      "type": "object"
+    },
+    "UsersSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "role_name": {
+              "const": "users"
+            },
+            "users": {
+              "items": {
+                "$ref": "#/$defs/UserEntry"
+              },
+              "type": "array"
+            }
+          },
+          "required": [
+            "users"
+          ],
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    },
+    "UsrLocalCustomSnapshot": {
+      "allOf": [
+        {
+          "$ref": "#/$defs/RoleCommon"
+        },
+        {
+          "properties": {
+            "role_name": {
+              "const": "usr_local_custom"
+            }
+          },
+          "type": "object"
+        }
+      ],
+      "unevaluatedProperties": false
+    }
+  },
+  "$id": "https://enroll.sh/schema/state.schema.json",
+  "$schema": "https://json-schema.org/draft/2020-12/schema",
+  "additionalProperties": false,
+  "properties": {
+    "enroll": {
+      "additionalProperties": false,
+      "properties": {
+        "harvest_time": {
+          "minimum": 0,
+          "type": "integer"
+        },
+        "version": {
+          "type": "string"
+        }
+      },
+      "required": [
+        "version",
+        "harvest_time"
+      ],
+      "type": "object"
+    },
+    "host": {
+      "additionalProperties": false,
+      "properties": {
+        "hostname": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "os": {
+          "enum": [
+            "debian",
+            "redhat",
+            "unknown"
+          ],
+          "type": "string"
+        },
+        "os_release": {
+          "additionalProperties": {
+            "type": "string"
+          },
+          "type": "object"
+        },
+        "pkg_backend": {
+          "enum": [
+            "dpkg",
+            "rpm"
+          ],
+          "type": "string"
+        }
+      },
+      "required": [
+        "hostname",
+        "os",
+        "pkg_backend",
+        "os_release"
+      ],
+      "type": "object"
+    },
+    "inventory": {
+      "additionalProperties": false,
+      "properties": {
+        "packages": {
+          "additionalProperties": {
+            "$ref": "#/$defs/PackageInventoryEntry"
+          },
+          "type": "object"
+        }
+      },
+      "required": [
+        "packages"
+      ],
+      "type": "object"
+    },
+    "roles": {
+      "additionalProperties": false,
+      "properties": {
+        "apt_config": {
+          "$ref": "#/$defs/AptConfigSnapshot"
+        },
+        "dnf_config": {
+          "$ref": "#/$defs/DnfConfigSnapshot"
+        },
+        "etc_custom": {
+          "$ref": "#/$defs/EtcCustomSnapshot"
+        },
+        "extra_paths": {
+          "$ref": "#/$defs/ExtraPathsSnapshot"
+        },
+        "packages": {
+          "items": {
+            "$ref": "#/$defs/PackageSnapshot"
+          },
+          "type": "array"
+        },
+        "services": {
+          "items": {
+            "$ref": "#/$defs/ServiceSnapshot"
+          },
+          "type": "array"
+        },
+        "users": {
+          "$ref": "#/$defs/UsersSnapshot"
+        },
+        "usr_local_custom": {
+          "$ref": "#/$defs/UsrLocalCustomSnapshot"
+        }
+      },
+      "required": [
+        "users",
+        "services",
+        "packages",
+        "apt_config",
+        "dnf_config",
+        "etc_custom",
+        "usr_local_custom",
+        "extra_paths"
+      ],
+      "type": "object"
+    }
+  },
+  "required": [
+    "enroll",
+    "host",
+    "inventory",
+    "roles"
+  ],
+  "title": "Enroll harvest state.json schema (latest)",
+  "type": "object"
+}

enroll/validate.py

@@ -0,0 +1,223 @@
+from __future__ import annotations
+
+import json
+import urllib.request
+from dataclasses import dataclass
+from pathlib import Path
+from typing import Any, Dict, List, Optional, Set, Tuple
+
+import jsonschema
+
+from .diff import BundleRef, _bundle_from_input
+
+
+@dataclass
+class ValidationResult:
+    errors: List[str]
+    warnings: List[str]
+
+    @property
+    def ok(self) -> bool:
+        return not self.errors
+
+    def to_dict(self) -> Dict[str, Any]:
+        return {
+            "ok": self.ok,
+            "errors": list(self.errors),
+            "warnings": list(self.warnings),
+        }
+
+    def to_text(self) -> str:
+        lines: List[str] = []
+        if not self.errors and not self.warnings:
+            lines.append("OK: harvest bundle validated")
+        elif not self.errors and self.warnings:
+            lines.append(f"WARN: {len(self.warnings)} warning(s)")
+        else:
+            lines.append(f"ERROR: {len(self.errors)} validation error(s)")
+
+        if self.errors:
+            lines.append("")
+            lines.append("Errors:")
+            for e in self.errors:
+                lines.append(f"- {e}")
+        if self.warnings:
+            lines.append("")
+            lines.append("Warnings:")
+            for w in self.warnings:
+                lines.append(f"- {w}")
+        return "\n".join(lines) + "\n"
+
+
+def _default_schema_path() -> Path:
+    # Keep the schema vendored with the codebase so enroll can validate offline.
+    return Path(__file__).resolve().parent / "schema" / "state.schema.json"
+
+
+def _load_schema(schema: Optional[str]) -> Dict[str, Any]:
+    """Load a JSON schema.
+
+    If schema is None, load the vendored schema.
+    If schema begins with http(s)://, fetch it.
+    Otherwise, treat it as a local file path.
+    """
+
+    if not schema:
+        p = _default_schema_path()
+        with open(p, "r", encoding="utf-8") as f:
+            return json.load(f)
+
+    if schema.startswith("http://") or schema.startswith("https://"):
+        with urllib.request.urlopen(schema, timeout=10) as resp:  # nosec
+            data = resp.read()
+        return json.loads(data.decode("utf-8"))
+
+    p = Path(schema).expanduser()
+    with open(p, "r", encoding="utf-8") as f:
+        return json.load(f)
+
+
+def _json_pointer(err: jsonschema.ValidationError) -> str:
+    # Build a JSON pointer-ish path that is easy to read.
+    if err.absolute_path:
+        parts = [str(p) for p in err.absolute_path]
+        return "/" + "/".join(parts)
+    return "/"
+
+
+def _iter_managed_files(state: Dict[str, Any]) -> List[Tuple[str, Dict[str, Any]]]:
+    """Return (role_name, managed_file_dict) tuples across all roles."""
+
+    roles = state.get("roles") or {}
+    out: List[Tuple[str, Dict[str, Any]]] = []
+
+    # Singleton roles
+    for rn in [
+        "users",
+        "apt_config",
+        "dnf_config",
+        "etc_custom",
+        "usr_local_custom",
+        "extra_paths",
+    ]:
+        snap = roles.get(rn) or {}
+        for mf in snap.get("managed_files") or []:
+            if isinstance(mf, dict):
+                out.append((rn, mf))
+
+    # Array roles
+    for s in roles.get("services") or []:
+        if not isinstance(s, dict):
+            continue
+        role_name = str(s.get("role_name") or "unknown")
+        for mf in s.get("managed_files") or []:
+            if isinstance(mf, dict):
+                out.append((role_name, mf))
+
+    for p in roles.get("packages") or []:
+        if not isinstance(p, dict):
+            continue
+        role_name = str(p.get("role_name") or "unknown")
+        for mf in p.get("managed_files") or []:
+            if isinstance(mf, dict):
+                out.append((role_name, mf))
+
+    return out
+
+
+def validate_harvest(
+    harvest_input: str,
+    *,
+    sops_mode: bool = False,
+    schema: Optional[str] = None,
+    no_schema: bool = False,
+) -> ValidationResult:
+    """Validate an enroll harvest bundle.
+
+    Checks:
+      - state.json parses
+      - state.json validates against the schema (unless no_schema)
+      - every managed_file src_rel exists in artifacts/<role>/<src_rel>
+    """
+
+    errors: List[str] = []
+    warnings: List[str] = []
+
+    bundle: BundleRef = _bundle_from_input(harvest_input, sops_mode=sops_mode)
+    try:
+        state_path = bundle.state_path
+        if not state_path.exists():
+            return ValidationResult(
+                errors=[f"missing state.json at {state_path}"], warnings=[]
+            )
+
+        try:
+            state = json.loads(state_path.read_text(encoding="utf-8"))
+        except Exception as e:  # noqa: BLE001
+            return ValidationResult(
+                errors=[f"failed to parse state.json: {e!r}"], warnings=[]
+            )
+
+        if not no_schema:
+            try:
+                sch = _load_schema(schema)
+                validator = jsonschema.Draft202012Validator(sch)
+                for err in sorted(validator.iter_errors(state), key=str):
+                    ptr = _json_pointer(err)
+                    msg = err.message
+                    errors.append(f"schema {ptr}: {msg}")
+            except Exception as e:  # noqa: BLE001
+                errors.append(f"failed to load/validate schema: {e!r}")
+
+        # Artifact existence checks
+        artifacts_dir = bundle.dir / "artifacts"
+        referenced: Set[Tuple[str, str]] = set()
+        for role_name, mf in _iter_managed_files(state):
+            src_rel = str(mf.get("src_rel") or "")
+            if not src_rel:
+                errors.append(
+                    f"managed_file missing src_rel for role {role_name} (path={mf.get('path')!r})"
+                )
+                continue
+            if src_rel.startswith("/") or ".." in src_rel.split("/"):
+                errors.append(
+                    f"managed_file has suspicious src_rel for role {role_name}: {src_rel!r}"
+                )
+                continue
+
+            referenced.add((role_name, src_rel))
+            p = artifacts_dir / role_name / src_rel
+            if not p.exists():
+                errors.append(
+                    f"missing artifact for role {role_name}: artifacts/{role_name}/{src_rel}"
+                )
+                continue
+            if not p.is_file():
+                errors.append(
+                    f"artifact is not a file for role {role_name}: artifacts/{role_name}/{src_rel}"
+                )
+
+        # Warn if there are extra files in artifacts not referenced.
+        if artifacts_dir.exists() and artifacts_dir.is_dir():
+            for fp in artifacts_dir.rglob("*"):
+                if not fp.is_file():
+                    continue
+                try:
+                    rel = fp.relative_to(artifacts_dir)
+                except ValueError:
+                    continue
+                parts = rel.parts
+                if len(parts) < 2:
+                    continue
+                role_name = parts[0]
+                src_rel = "/".join(parts[1:])
+                if (role_name, src_rel) not in referenced:
+                    warnings.append(
+                        f"unreferenced artifact present: artifacts/{role_name}/{src_rel}"
+                    )
+
+        return ValidationResult(errors=errors, warnings=warnings)
+    finally:
+        # Ensure any temp extraction dirs are cleaned up.
+        if bundle.tempdir is not None:
+            bundle.tempdir.cleanup()

poetry.lock

@@ -1,5 +1,16 @@
 # This file is automatically @generated by Poetry 1.8.3 and should not be changed by hand.
 
+[[package]]
+name = "attrs"
+version = "25.4.0"
+description = "Classes Without Boilerplate"
+optional = false
+python-versions = ">=3.9"
+files = [
+    {file = "attrs-25.4.0-py3-none-any.whl", hash = "sha256:adcf7e2a1fb3b36ac48d97835bb6d8ade15b8dcce26aba8bf1d14847b57a3373"},
+    {file = "attrs-25.4.0.tar.gz", hash = "sha256:16d5969b87f0859ef33a48b35d55ac1be6e42ae49d5e853b597db70c35c57e11"},
+]
+
 [[package]]
 name = "bcrypt"
 version = "5.0.0"
@@ -78,13 +89,13 @@ typecheck = ["mypy"]
 
 [[package]]
 name = "certifi"
-version = "2025.11.12"
+version = "2026.1.4"
 description = "Python package for providing Mozilla's CA Bundle."
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "certifi-2025.11.12-py3-none-any.whl", hash = "sha256:97de8790030bbd5c2d96b7ec782fc2f7820ef8dba6db909ccf95449f2d062d4b"},
-    {file = "certifi-2025.11.12.tar.gz", hash = "sha256:d8ab5478f2ecd78af242878415affce761ca6bc54a22a27e026d7c25357c3316"},
+    {file = "certifi-2026.1.4-py3-none-any.whl", hash = "sha256:9943707519e4add1115f44c2bc244f782c0249876bf51b6599fee1ffbedd685c"},
+    {file = "certifi-2026.1.4.tar.gz", hash = "sha256:ac726dd470482006e014ad384921ed6438c457018f4b3d204aea4281258b2120"},
 ]
 
 [[package]]
@@ -318,103 +329,103 @@ files = [
 
 [[package]]
 name = "coverage"
-version = "7.13.0"
+version = "7.13.1"
 description = "Code coverage measurement for Python"
 optional = false
 python-versions = ">=3.10"
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 [package.dependencies]
@@ -425,65 +436,60 @@ toml = ["tomli"]
 
 [[package]]
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 optional = false
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 test-randomorder = ["pytest-randomly"]
 
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 ]
 
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+
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+referencing = ">=0.28.4"
+rpds-py = ">=0.25.0"
+
+[package.extras]
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+
+[[package]]
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+version = "2025.9.1"
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+python-versions = ">=3.9"
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+
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 name = "packaging"
 version = "25.0"
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+version = "1.6.2"
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 [package.dependencies]
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 ]
 
+[[package]]
+name = "referencing"
+version = "0.37.0"
+description = "JSON Referencing + Python"
+optional = false
+python-versions = ">=3.10"
+files = [
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+
+[package.dependencies]
+attrs = ">=22.2.0"
+rpds-py = ">=0.7.0"
+typing-extensions = {version = ">=4.4.0", markers = "python_version < \"3.13\""}
+
 [[package]]
 name = "requests"
 version = "2.32.5"
@@ -841,55 +896,184 @@ urllib3 = ">=1.21.1,<3"
 socks = ["PySocks (>=1.5.6,!=1.5.7)"]
 use-chardet-on-py3 = ["chardet (>=3.0.2,<6)"]
 
+[[package]]
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+optional = false
+python-versions = ">=3.10"
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 ]
 
 [[package]]
@@ -905,13 +1089,13 @@ files = [
 
 [[package]]
 name = "urllib3"
-version = "2.6.2"
+version = "2.6.3"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 optional = false
 python-versions = ">=3.9"
 files = [
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+    {file = "urllib3-2.6.3.tar.gz", hash = "sha256:1b62b6884944a57dbe321509ab94fd4d3b307075e0c2eae991ac71ee15ad38ed"},
 ]
 
 [package.extras]
@@ -923,4 +1107,4 @@ zstd = ["backports-zstd (>=1.0.0)"]
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.10"
-content-hash = "20623104a1a5f4c6d4aaa759f25b2591d5de345d1464e727eb4140a6ef9a5b6e"
+content-hash = "30e16396439f2cdd69005a5b7bdf8144aac33422a77a63accbc9eaa74151d851"

pyproject.toml

@@ -1,17 +1,21 @@
 [tool.poetry]
 name = "enroll"
-version = "0.2.0"
+version = "0.4.4"
 description = "Enroll a server's running state retrospectively into Ansible"
 authors = ["Miguel Jacq <mig@mig5.net>"]
 license = "GPL-3.0-or-later"
 readme = "README.md"
 packages = [{ include = "enroll" }]
 repository = "https://git.mig5.net/mig5/enroll"
+include = [
+  { path = "enroll/schema/state.schema.json", format = ["sdist", "wheel"] }
+]
 
 [tool.poetry.dependencies]
 python = "^3.10"
 pyyaml = "^6"
 paramiko = ">=3.5"
+jsonschema = "^4.23.0"
 
 [tool.poetry.scripts]
 enroll = "enroll.cli:main"

release.sh

@@ -45,30 +45,48 @@ done
 
 # RPM
 sudo apt-get -y install createrepo-c rpm
-docker build -f Dockerfile.rpmbuild -t enroll:f42 --progress=plain .
-docker run --rm -v "$PWD":/src -v "$PWD/dist/rpm":/out -v "$HOME/git/jinjaturtle/dist/rpm":/deps:ro enroll:f42
-sudo chown -R "${USER}" "$PWD/dist"
-
-REPO_ROOT="${HOME}/git/repo_rpm"
-RPM_REPO="${REPO_ROOT}/rpm/x86_64"
 BUILD_OUTPUT="${HOME}/git/enroll/dist"
-REMOTE="letessier.mig5.net:/opt/repo_rpm"
 KEYID="00AE817C24A10C2540461A9C1D7CDE0234DB458D"
+REPO_ROOT="${HOME}/git/repo_rpm"
+REMOTE="letessier.mig5.net:/opt/repo_rpm"
 
-echo "==> Updating RPM repo..."
-mkdir -p "$RPM_REPO"
+DISTS=(
+  fedora:43
+  fedora:42
+)
 
-for file in `ls -1 "${BUILD_OUTPUT}/rpm"`; do
-  rpmsign --addsign "${BUILD_OUTPUT}/rpm/$file"
+for dist in ${DISTS[@]}; do
+  release=$(echo ${dist} | cut -d: -f2)
+  REPO_RELEASE_ROOT="${REPO_ROOT}/${release}"
+  RPM_REPO="${REPO_RELEASE_ROOT}/rpm/x86_64"
+  mkdir -p "$RPM_REPO"
+
+  docker build \
+    --no-cache \
+    -f Dockerfile.rpmbuild \
+    -t enroll-rpm:${release} \
+    --progress=plain \
+    --build-arg BASE_IMAGE=${dist} \
+    .
+
+  rm -rf "$PWD/dist/rpm"/*
+  mkdir -p "$PWD/dist/rpm"
+
+  docker run --rm -v "$PWD":/src -v "$PWD/dist/rpm":/out enroll-rpm:${release}
+  sudo chown -R "${USER}" "$PWD/dist"
+
+  for file in `ls -1 "${BUILD_OUTPUT}/rpm"`; do
+    rpmsign --addsign "${BUILD_OUTPUT}/rpm/$file"
+  done
+
+  cp "${BUILD_OUTPUT}/rpm/"*.rpm "$RPM_REPO/"
+
+  createrepo_c "$RPM_REPO"
+
+  echo "==> Signing repomd.xml..."
+  qubes-gpg-client --local-user "$KEYID" --detach-sign --armor "$RPM_REPO/repodata/repomd.xml" > "$RPM_REPO/repodata/repomd.xml.asc"
 done
 
-cp "${BUILD_OUTPUT}/rpm/"*.rpm "$RPM_REPO/"
-
-createrepo_c "$RPM_REPO"
-
-echo "==> Signing repomd.xml..."
-qubes-gpg-client --local-user "$KEYID" --detach-sign --armor "$RPM_REPO/repodata/repomd.xml" > "$RPM_REPO/repodata/repomd.xml.asc"
-
 echo "==> Syncing repo to server..."
 rsync -aHPvz --exclude=.git --delete "$REPO_ROOT/" "$REMOTE/"
 

rpm/enroll.spec

@@ -1,4 +1,4 @@
-%global upstream_version 0.2.0
+%global upstream_version 0.4.4
 
 Name:           enroll
 Version:        %{upstream_version}
@@ -17,8 +17,8 @@ BuildRequires:  python3-poetry-core
 
 Requires: python3-yaml
 Requires: python3-paramiko
+Requires: python3-jsonschema
 
-# Make sure private repo dependency is pulled in by package name as well.
 Recommends:       jinjaturtle
 
 %description
@@ -43,6 +43,38 @@ Enroll a server's running state retrospectively into Ansible.
 %{_bindir}/enroll
 
 %changelog
+* Tue Feb 16 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Add capability to handle passphrases on encrypted SSH private keys. Prompting can be forced with `--ask-key-passphrase` or automated (e.g for CI) with `--ssh-key-passphrase env SOMEVAR`
+* Fri Jan 16 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Add support for AddressFamily and ConnectTimeout in the .ssh/config when using `--remote-ssh-config`.
+* Tue Jan 13 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Support `--remote-ssh-config [path-to-ssh-config]` as an argument in case extra params are required beyond `--remote-port` or `--remote-user`. Note: `--remote-host` must still be s
+et, but it can be an 'alias' represented by the 'Host' value in the ssh config.
+* Sun Jan 11 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Add interactive output when 'enroll diff --enforce' is invoking Ansible.
+* Sat Jan 10 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Introduce `enroll validate` - a tool to validate a harvest against the state schema, or check for missing or orphaned obsolete artifacts in a harvest.
+- Attempt to generate Jinja2 templates of systemd unit files and Postfix main.cf (now that JinjaTurtle supports it)
+- Update pynacl dependency to resolve CVE-2025-69277
+- Add `--exclude-path` to `enroll diff` command, so that you can ignore certain churn from the diff (stuff you still wanted to harvest as a baseline but don't care if it changes day to day)
+- Add `--ignore-package-versions` to `enroll diff` command, to optionally ignore package upgrades (e.g due to patching) from the diff.
+- Add tags to the playbook for each role, to allow easier targeting of specific roles during play later.
+- Add `--enforce` mode to `enroll diff`. If there is diff detected between the two harvests, and it can enforce restoring the state from the older harvest, it will manifest the state and apply it with ansible.
+Only the specific roles that had diffed will be applied (via the new tags capability)
+* Mon Jan 05 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Introduce `enroll explain` - a tool to analyze and explain what's in (or not in) a harvest and why.
+- Centralise the cron and logrotate stuff into their respective roles, we had a bit of duplication between roles based on harvest discovery.
+- Capture other files in the user's home directory such as `.bashrc`, `.bash_aliases`, `.profile`, if these files differ from the `/etc/skel` defaults
+- Ignore files that end with a tilde or - (probably backup files generated by editors or shadow file changes)
+- Manage certain symlinks e.g for apache2/nginx sites-enabled and so on
+* Sun Jan 04 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Introduce --ask-become-pass or -K to support password-required sudo on remote hosts, just like Ansible. It will also fall back to this prompt if a password is required but the arg wasn't passed in.
+* Sat Jan 03 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Fix stat() of parent directory so that we set directory perms correct on --include paths.
+- Set pty for remote calls when sudo is required, to help systems with limits on sudo without pty
+* Fri Jan 02 2026 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
+- Don't accidentally add extra_paths role to usr_local_custom list, resulting in extra_paths appearing twice in manifested playbook
+- Ensure directories in the tree of anything included with --include are defined in the state and manifest so we make dirs before we try to create files
 * Mon Dec 29 2025 Miguel Jacq <mig@mig5.net> - %{version}-%{release}
 - Add version CLI arg
 - Add ability to enroll RH-style systems (DNF5/DNF/RPM)

tests.sh

@@ -9,14 +9,43 @@ BUNDLE_DIR="/tmp/bundle"
 ANSIBLE_DIR="/tmp/ansible"
 rm -rf "${BUNDLE_DIR}" "${ANSIBLE_DIR}"
 
+# Install something that has symlinks like apache2,
+# to extend the manifests that will be linted later
+DEBIAN_FRONTEND=noninteractive apt-get install -y --no-install-recommends apache2
+
 # Generate data
 poetry run \
 	enroll single-shot \
 	  --harvest "${BUNDLE_DIR}" \
 	  --out "${ANSIBLE_DIR}"
 
-builtin cd "${ANSIBLE_DIR}"
+# Analyse
+poetry run \
+	enroll explain "${BUNDLE_DIR}"
+poetry run \
+        enroll explain "${BUNDLE_DIR}" --format json | jq
 
+# Validate
+poetry run \
+	enroll validate --fail-on-warnings "${BUNDLE_DIR}"
+
+# Install/remove something, harvest again and diff the harvests
+DEBIAN_FRONTEND=noninteractive apt-get install -y --no-install-recommends cowsay
+poetry run \
+	enroll harvest --out "${BUNDLE_DIR}2"
+# Validate
+poetry run \
+	enroll validate --fail-on-warnings "${BUNDLE_DIR}2"
+# Diff
+poetry run \
+	enroll diff \
+	  --old "${BUNDLE_DIR}" \
+	  --new "${BUNDLE_DIR}2" \
+	  --format json | jq
+DEBIAN_FRONTEND=noninteractive apt-get remove -y --purge cowsay
+
+# Ansible test
+builtin cd "${ANSIBLE_DIR}"
 # Lint
 ansible-lint "${ANSIBLE_DIR}"
 

tests/test_cache_security.py

@@ -0,0 +1,33 @@
+from __future__ import annotations
+
+import os
+from pathlib import Path
+
+import pytest
+
+
+def test_ensure_dir_secure_refuses_symlink(tmp_path: Path):
+    from enroll.cache import _ensure_dir_secure
+
+    target = tmp_path / "target"
+    target.mkdir()
+    link = tmp_path / "link"
+    link.symlink_to(target, target_is_directory=True)
+
+    with pytest.raises(RuntimeError):
+        _ensure_dir_secure(link)
+
+
+def test_ensure_dir_secure_ignores_chmod_failures(tmp_path: Path, monkeypatch):
+    from enroll.cache import _ensure_dir_secure
+
+    d = tmp_path / "d"
+
+    def boom(_path: str, _mode: int):
+        raise OSError("no")
+
+    monkeypatch.setattr(os, "chmod", boom)
+
+    # Should not raise.
+    _ensure_dir_secure(d)
+    assert d.exists() and d.is_dir()

tests/test_cli.py

@@ -1,7 +1,14 @@
+from __future__ import annotations
 import sys
 
+import pytest
 import enroll.cli as cli
 
+from pathlib import Path
+
+from enroll.remote import RemoteSudoPasswordRequired
+from enroll.sopsutil import SopsError
+
 
 def test_cli_harvest_subcommand_calls_harvest(monkeypatch, capsys, tmp_path):
     called = {}
@@ -258,6 +265,113 @@ def test_cli_single_shot_remote_without_harvest_prints_state_path(
     assert ("manifest", str(cache_dir), str(ansible_dir), "example.test") in calls
 
 
+def test_cli_harvest_remote_ask_become_pass_prompts_and_passes_password(
+    monkeypatch, tmp_path
+):
+    from enroll.cache import HarvestCache
+    import enroll.remote as r
+
+    cache_dir = tmp_path / "cache"
+    cache_dir.mkdir()
+
+    called = {}
+
+    def fake_cache_dir(*, hint=None):
+        return HarvestCache(dir=cache_dir)
+
+    def fake__remote_harvest(*, sudo_password=None, **kwargs):
+        called["sudo_password"] = sudo_password
+        return cache_dir / "state.json"
+
+    monkeypatch.setattr(cli, "new_harvest_cache_dir", fake_cache_dir)
+    monkeypatch.setattr(r, "_remote_harvest", fake__remote_harvest)
+    monkeypatch.setattr(r.getpass, "getpass", lambda _prompt="": "pw123")
+
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "harvest",
+            "--remote-host",
+            "example.test",
+            "--ask-become-pass",
+        ],
+    )
+
+    cli.main()
+    assert called["sudo_password"] == "pw123"
+
+
+def test_cli_harvest_remote_password_required_fallback_prompts_and_retries(
+    monkeypatch, tmp_path
+):
+    from enroll.cache import HarvestCache
+    import enroll.remote as r
+
+    cache_dir = tmp_path / "cache"
+    cache_dir.mkdir()
+
+    def fake_cache_dir(*, hint=None):
+        return HarvestCache(dir=cache_dir)
+
+    calls = []
+
+    def fake__remote_harvest(*, sudo_password=None, **kwargs):
+        calls.append(sudo_password)
+        if sudo_password is None:
+            raise r.RemoteSudoPasswordRequired("pw required")
+        return cache_dir / "state.json"
+
+    class _TTYStdin:
+        def isatty(self):
+            return True
+
+    monkeypatch.setattr(cli, "new_harvest_cache_dir", fake_cache_dir)
+    monkeypatch.setattr(r, "_remote_harvest", fake__remote_harvest)
+    monkeypatch.setattr(r.getpass, "getpass", lambda _prompt="": "pw456")
+    monkeypatch.setattr(sys, "stdin", _TTYStdin())
+
+    monkeypatch.setattr(
+        sys, "argv", ["enroll", "harvest", "--remote-host", "example.test"]
+    )
+
+    cli.main()
+    assert calls == [None, "pw456"]
+
+
+def test_cli_harvest_remote_password_required_noninteractive_errors(
+    monkeypatch, tmp_path
+):
+    from enroll.cache import HarvestCache
+    import enroll.remote as r
+
+    cache_dir = tmp_path / "cache"
+    cache_dir.mkdir()
+
+    def fake_cache_dir(*, hint=None):
+        return HarvestCache(dir=cache_dir)
+
+    def fake__remote_harvest(*, sudo_password=None, **kwargs):
+        raise r.RemoteSudoPasswordRequired("pw required")
+
+    class _NoTTYStdin:
+        def isatty(self):
+            return False
+
+    monkeypatch.setattr(cli, "new_harvest_cache_dir", fake_cache_dir)
+    monkeypatch.setattr(r, "_remote_harvest", fake__remote_harvest)
+    monkeypatch.setattr(sys, "stdin", _NoTTYStdin())
+
+    monkeypatch.setattr(
+        sys, "argv", ["enroll", "harvest", "--remote-host", "example.test"]
+    )
+
+    with pytest.raises(SystemExit) as e:
+        cli.main()
+    assert "--ask-become-pass" in str(e.value)
+
+
 def test_cli_manifest_common_args(monkeypatch, tmp_path):
     """Ensure --fqdn and jinjaturtle mode flags are forwarded correctly."""
 
@@ -289,3 +403,286 @@ def test_cli_manifest_common_args(monkeypatch, tmp_path):
     cli.main()
     assert called["fqdn"] == "example.test"
     assert called["jinjaturtle"] == "off"
+
+
+def test_cli_explain_passes_args_and_writes_stdout(monkeypatch, capsys, tmp_path):
+    called = {}
+
+    def fake_explain_state(
+        harvest: str,
+        *,
+        sops_mode: bool = False,
+        fmt: str = "text",
+        max_examples: int = 3,
+    ):
+        called["harvest"] = harvest
+        called["sops_mode"] = sops_mode
+        called["fmt"] = fmt
+        called["max_examples"] = max_examples
+        return "EXPLAINED\n"
+
+    monkeypatch.setattr(cli, "explain_state", fake_explain_state)
+
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "explain",
+            "--sops",
+            "--format",
+            "json",
+            "--max-examples",
+            "7",
+            str(tmp_path / "bundle" / "state.json"),
+        ],
+    )
+
+    cli.main()
+    out = capsys.readouterr().out
+    assert out == "EXPLAINED\n"
+    assert called["sops_mode"] is True
+    assert called["fmt"] == "json"
+    assert called["max_examples"] == 7
+
+
+def test_discover_config_path_missing_config_value_returns_none(monkeypatch):
+    # Covers the "--config" flag present with no value.
+    monkeypatch.delenv("ENROLL_CONFIG", raising=False)
+    monkeypatch.delenv("XDG_CONFIG_HOME", raising=False)
+    assert cli._discover_config_path(["--config"]) is None
+
+
+def test_discover_config_path_defaults_to_home_config(monkeypatch, tmp_path: Path):
+    # Covers the Path.home() / ".config" fallback.
+    monkeypatch.delenv("ENROLL_CONFIG", raising=False)
+    monkeypatch.delenv("XDG_CONFIG_HOME", raising=False)
+    monkeypatch.setattr(cli.Path, "home", lambda: tmp_path)
+    monkeypatch.setattr(cli.Path, "cwd", lambda: tmp_path)
+
+    cp = tmp_path / ".config" / "enroll" / "enroll.ini"
+    cp.parent.mkdir(parents=True)
+    cp.write_text("[enroll]\n", encoding="utf-8")
+
+    assert cli._discover_config_path(["harvest"]) == cp
+
+
+def test_cli_harvest_local_sops_encrypts_and_prints_path(
+    monkeypatch, tmp_path: Path, capsys
+):
+    out_dir = tmp_path / "out"
+    out_dir.mkdir()
+    calls: dict[str, object] = {}
+
+    def fake_harvest(bundle_dir: str, **kwargs):
+        calls["bundle"] = bundle_dir
+        # Create a minimal state.json so tooling that expects it won't break.
+        Path(bundle_dir).mkdir(parents=True, exist_ok=True)
+        (Path(bundle_dir) / "state.json").write_text("{}", encoding="utf-8")
+        return str(Path(bundle_dir) / "state.json")
+
+    def fake_encrypt(bundle_dir: Path, out_file: Path, fps: list[str]):
+        calls["encrypt"] = (bundle_dir, out_file, fps)
+        out_file.write_text("encrypted", encoding="utf-8")
+        return out_file
+
+    monkeypatch.setattr(cli, "harvest", fake_harvest)
+    monkeypatch.setattr(cli, "_encrypt_harvest_dir_to_sops", fake_encrypt)
+
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "harvest",
+            "--sops",
+            "ABCDEF",
+            "--out",
+            str(out_dir),
+        ],
+    )
+    cli.main()
+
+    printed = capsys.readouterr().out.strip()
+    assert printed.endswith("harvest.tar.gz.sops")
+    assert Path(printed).exists()
+    assert calls.get("encrypt")
+
+
+def test_cli_harvest_remote_sops_encrypts_and_prints_path(
+    monkeypatch, tmp_path: Path, capsys
+):
+    out_dir = tmp_path / "out"
+    out_dir.mkdir()
+    calls: dict[str, object] = {}
+
+    def fake_remote_harvest(**kwargs):
+        calls["remote"] = kwargs
+        # Create a minimal state.json in the temp bundle.
+        out = Path(kwargs["local_out_dir"]) / "state.json"
+        out.write_text("{}", encoding="utf-8")
+        return out
+
+    def fake_encrypt(bundle_dir: Path, out_file: Path, fps: list[str]):
+        calls["encrypt"] = (bundle_dir, out_file, fps)
+        out_file.write_text("encrypted", encoding="utf-8")
+        return out_file
+
+    monkeypatch.setattr(cli, "remote_harvest", fake_remote_harvest)
+    monkeypatch.setattr(cli, "_encrypt_harvest_dir_to_sops", fake_encrypt)
+
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "harvest",
+            "--remote-host",
+            "example.com",
+            "--remote-user",
+            "root",
+            "--sops",
+            "ABCDEF",
+            "--out",
+            str(out_dir),
+        ],
+    )
+    cli.main()
+
+    printed = capsys.readouterr().out.strip()
+    assert printed.endswith("harvest.tar.gz.sops")
+    assert Path(printed).exists()
+    assert calls.get("remote")
+    assert calls.get("encrypt")
+
+
+def test_cli_harvest_remote_password_required_exits_cleanly(monkeypatch):
+    def boom(**kwargs):
+        raise RemoteSudoPasswordRequired("pw required")
+
+    monkeypatch.setattr(cli, "remote_harvest", boom)
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "harvest",
+            "--remote-host",
+            "example.com",
+            "--remote-user",
+            "root",
+        ],
+    )
+    with pytest.raises(SystemExit) as e:
+        cli.main()
+    assert "--ask-become-pass" in str(e.value)
+
+
+def test_cli_runtime_error_is_wrapped_as_user_friendly_system_exit(monkeypatch):
+    def boom(*args, **kwargs):
+        raise RuntimeError("nope")
+
+    monkeypatch.setattr(cli, "harvest", boom)
+    monkeypatch.setattr(sys, "argv", ["enroll", "harvest", "--out", "/tmp/x"])
+    with pytest.raises(SystemExit) as e:
+        cli.main()
+    assert str(e.value) == "error: nope"
+
+
+def test_cli_sops_error_is_wrapped_as_user_friendly_system_exit(monkeypatch):
+    def boom(*args, **kwargs):
+        raise SopsError("sops broke")
+
+    monkeypatch.setattr(cli, "manifest", boom)
+    monkeypatch.setattr(
+        sys, "argv", ["enroll", "manifest", "--harvest", "/tmp/x", "--out", "/tmp/y"]
+    )
+    with pytest.raises(SystemExit) as e:
+        cli.main()
+    assert str(e.value) == "error: sops broke"
+
+
+def test_cli_diff_notifies_webhook_and_email_and_respects_exit_code(
+    monkeypatch, capsys
+):
+    calls: dict[str, object] = {}
+
+    def fake_compare(old, new, sops_mode=False, **kwargs):
+        calls["compare"] = (old, new, sops_mode)
+        return {"dummy": True}, True
+
+    def fake_format(report, fmt="text"):
+        calls.setdefault("format", []).append((report, fmt))
+        return "REPORT\n"
+
+    def fake_post(url, body, headers=None):
+        calls["webhook"] = (url, body, headers)
+        return 200, b"ok"
+
+    def fake_email(**kwargs):
+        calls["email"] = kwargs
+
+    monkeypatch.setattr(cli, "compare_harvests", fake_compare)
+    monkeypatch.setattr(cli, "format_report", fake_format)
+    monkeypatch.setattr(cli, "post_webhook", fake_post)
+    monkeypatch.setattr(cli, "send_email", fake_email)
+    monkeypatch.setenv("SMTPPW", "secret")
+
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "diff",
+            "--old",
+            "/tmp/old",
+            "--new",
+            "/tmp/new",
+            "--webhook",
+            "https://example.invalid/h",
+            "--webhook-header",
+            "X-Test: ok",
+            "--email-to",
+            "a@example.com",
+            "--smtp-password-env",
+            "SMTPPW",
+            "--exit-code",
+        ],
+    )
+
+    with pytest.raises(SystemExit) as e:
+        cli.main()
+    assert e.value.code == 2
+
+    assert calls.get("compare")
+    assert calls.get("webhook")
+    assert calls.get("email")
+    # No report printed when exiting via --exit-code? (we still render and print).
+    _ = capsys.readouterr()
+
+
+def test_cli_diff_webhook_http_error_raises_system_exit(monkeypatch):
+    def fake_compare(old, new, sops_mode=False, **kwargs):
+        return {"dummy": True}, True
+
+    monkeypatch.setattr(cli, "compare_harvests", fake_compare)
+    monkeypatch.setattr(cli, "format_report", lambda report, fmt="text": "R\n")
+    monkeypatch.setattr(cli, "post_webhook", lambda url, body, headers=None: (500, b""))
+
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        [
+            "enroll",
+            "diff",
+            "--old",
+            "/tmp/old",
+            "--new",
+            "/tmp/new",
+            "--webhook",
+            "https://example.invalid/h",
+        ],
+    )
+    with pytest.raises(SystemExit) as e:
+        cli.main()
+    assert "HTTP 500" in str(e.value)

tests/test_cli_config_and_sops.py

@@ -0,0 +1,189 @@
+from __future__ import annotations
+
+import argparse
+import configparser
+import tarfile
+from pathlib import Path
+
+
+def test_discover_config_path_precedence(monkeypatch, tmp_path: Path):
+    from enroll.cli import _discover_config_path
+
+    cfg = tmp_path / "cfg.ini"
+    cfg.write_text("[enroll]\n", encoding="utf-8")
+
+    # --no-config always wins
+    monkeypatch.setenv("ENROLL_CONFIG", str(cfg))
+    assert _discover_config_path(["--no-config", "harvest"]) is None
+
+    # explicit --config wins
+    assert _discover_config_path(["--config", str(cfg), "harvest"]) == cfg
+
+    # env var used when present
+    assert _discover_config_path(["harvest"]) == cfg
+
+
+def test_discover_config_path_finds_local_and_xdg(monkeypatch, tmp_path: Path):
+    from enroll.cli import _discover_config_path
+
+    # local file in cwd
+    cwd = tmp_path / "cwd"
+    cwd.mkdir()
+    local = cwd / "enroll.ini"
+    local.write_text("[enroll]\n", encoding="utf-8")
+
+    monkeypatch.chdir(cwd)
+    monkeypatch.delenv("ENROLL_CONFIG", raising=False)
+    monkeypatch.delenv("XDG_CONFIG_HOME", raising=False)
+    assert _discover_config_path(["harvest"]) == local
+
+    # xdg config fallback
+    monkeypatch.chdir(tmp_path)
+    xdg = tmp_path / "xdg"
+    (xdg / "enroll").mkdir(parents=True)
+    xcfg = xdg / "enroll" / "enroll.ini"
+    xcfg.write_text("[enroll]\n", encoding="utf-8")
+    monkeypatch.setenv("XDG_CONFIG_HOME", str(xdg))
+    assert _discover_config_path(["harvest"]) == xcfg
+
+
+def test_section_to_argv_supports_bool_append_count_and_unknown(monkeypatch, capsys):
+    from enroll.cli import _section_to_argv
+
+    ap = argparse.ArgumentParser(add_help=False)
+    ap.add_argument("--flag", action="store_true")
+    ap</