diff --git a/CHANGELOG.md b/CHANGELOG.md
index a27c1c4..55af76b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,7 @@
  * Represent in the History diff pane when an image was the thing that changed
  * Support theme choice in settings (light/dark/system)
  * Add Checkboxes in the editor. Typing 'TODO' at the start of a line will auto-convert into a checkbox.
+ * Add option to automatically move yesterday's unchecked TODOs to today on startup
 
 # 0.1.9
 
diff --git a/bouquin/db.py b/bouquin/db.py
index e8c4903..20261eb 100644
--- a/bouquin/db.py
+++ b/bouquin/db.py
@@ -20,6 +20,7 @@ class DBConfig:
     key: str
     idle_minutes: int = 15  # 0 = never lock
     theme: str = "system"
+    move_todos: bool = False
 
 
 class DBManager:
diff --git a/bouquin/editor.py b/bouquin/editor.py
index 05ef128..5abf9b8 100644
--- a/bouquin/editor.py
+++ b/bouquin/editor.py
@@ -886,5 +886,12 @@ class Editor(QTextEdit):
 
     def setHtml(self, html: str) -> None:
         super().setHtml(html)
+
+        doc = self.document()
+        block = doc.firstBlock()
+        while block.isValid():
+            self._style_checkbox_glyph(block)  # Apply checkbox styling to each block
+            block = block.next()
+
         # Ensure anchors adopt the palette color on startup
         self._retint_anchors_to_palette()
diff --git a/bouquin/main_window.py b/bouquin/main_window.py
index 7c9d1d0..9243177 100644
--- a/bouquin/main_window.py
+++ b/bouquin/main_window.py
@@ -3,6 +3,7 @@ from __future__ import annotations
 import datetime
 import os
 import sys
+import re
 
 from pathlib import Path
 from PySide6.QtCore import (
@@ -224,7 +225,8 @@ class MainWindow(QMainWindow):
         self.editor.textChanged.connect(self._on_text_changed)
 
         # First load + mark dates in calendar with content
-        self._load_selected_date()
+        if not self._load_yesterday_todos():
+            self._load_selected_date()
         self._refresh_calendar_marks()
 
         # Restore window position from settings
@@ -469,17 +471,31 @@ class MainWindow(QMainWindow):
         d = self.calendar.selectedDate()
         return f"{d.year():04d}-{d.month():02d}-{d.day():02d}"
 
-    def _load_selected_date(self, date_iso=False):
+    def _load_selected_date(self, date_iso=False, extra_data=False):
         if not date_iso:
             date_iso = self._current_date_iso()
         try:
             text = self.db.get_entry(date_iso)
+            if extra_data:
+                # Wrap extra_data in a <p> tag for HTML rendering
+                extra_data_html = f"<p>{extra_data}</p>"
+
+                # Inject the extra_data before the closing </body></html>
+                modified = re.sub(r"(<\/body><\/html>)", extra_data_html + r"\1", text)
+                text = modified
+                self.editor.setHtml(text)
+                self._dirty = True
+                self._save_date(date_iso, True)
+
+            print("end")
         except Exception as e:
             QMessageBox.critical(self, "Read Error", str(e))
             return
+
         self.editor.blockSignals(True)
         self.editor.setHtml(text)
         self.editor.blockSignals(False)
+
         self._dirty = False
         # track which date the editor currently represents
         self._active_date_iso = date_iso
@@ -500,6 +516,56 @@ class MainWindow(QMainWindow):
         today = QDate.currentDate()
         self.calendar.setSelectedDate(today)
 
+    def _load_yesterday_todos(self):
+        try:
+            if not self.cfg.move_todos:
+                return
+            yesterday_str = QDate.currentDate().addDays(-1).toString("yyyy-MM-dd")
+            text = self.db.get_entry(yesterday_str)
+            unchecked_items = []
+
+            # Regex to match the unchecked checkboxes and their associated text
+            checkbox_pattern = re.compile(
+                r"<span[^>]*>(☐)</span>\s*(.*?)</p>", re.DOTALL
+            )
+
+            # Find unchecked items and store them
+            for match in checkbox_pattern.finditer(text):
+                checkbox = match.group(1)  # Either ☐ or ☑
+                item_text = match.group(2).strip()  # The text after the checkbox
+                if checkbox == "☐":  # If it's an unchecked checkbox (☐)
+                    unchecked_items.append("☐ " + item_text)  # Store the unchecked item
+
+            # Remove the unchecked items from yesterday's HTML content
+            if unchecked_items:
+                # This regex will find the entire checkbox line and remove it from the HTML content
+                uncheckbox_pattern = re.compile(
+                    r"<span[^>]*>☐</span>\s*(.*?)</p>", re.DOTALL
+                )
+                modified_text = re.sub(
+                    uncheckbox_pattern, "", text
+                )  # Remove the checkbox lines
+
+                # Save the modified HTML back to the database
+                self.db.save_new_version(
+                    yesterday_str,
+                    modified_text,
+                    "Unchecked checkbox items moved to next day",
+                )
+
+                # Join unchecked items into a formatted string
+                unchecked_str = "\n".join(
+                    [f"<p>{item}</p>" for item in unchecked_items]
+                )
+
+                # Load the unchecked items into the current editor
+                self._load_selected_date(False, unchecked_str)
+            else:
+                return False
+
+        except Exception as e:
+            raise SystemError(e)
+
     def _on_date_changed(self):
         """
         When the calendar selection changes, save the previous day's note if dirty,
@@ -592,6 +658,7 @@ class MainWindow(QMainWindow):
         self.cfg.key = new_cfg.key
         self.cfg.idle_minutes = getattr(new_cfg, "idle_minutes", self.cfg.idle_minutes)
         self.cfg.theme = getattr(new_cfg, "theme", self.cfg.theme)
+        self.cfg.move_todos = getattr(new_cfg, "move_todos", self.cfg.move_todos)
 
         # Persist once
         save_db_config(self.cfg)
diff --git a/bouquin/settings.py b/bouquin/settings.py
index 8860ed2..2201b09 100644
--- a/bouquin/settings.py
+++ b/bouquin/settings.py
@@ -24,7 +24,10 @@ def load_db_config() -> DBConfig:
     key = s.value("db/key", "")
     idle = s.value("ui/idle_minutes", 15, type=int)
     theme = s.value("ui/theme", "system", type=str)
-    return DBConfig(path=path, key=key, idle_minutes=idle, theme=theme)
+    move_todos = s.value("ui/move_todos", False, type=bool)
+    return DBConfig(
+        path=path, key=key, idle_minutes=idle, theme=theme, move_todos=move_todos
+    )
 
 
 def save_db_config(cfg: DBConfig) -> None:
@@ -33,3 +36,4 @@ def save_db_config(cfg: DBConfig) -> None:
     s.setValue("db/key", str(cfg.key))
     s.setValue("ui/idle_minutes", str(cfg.idle_minutes))
     s.setValue("ui/theme", str(cfg.theme))
+    s.setValue("ui/move_todos", str(cfg.move_todos))
diff --git a/bouquin/settings_dialog.py b/bouquin/settings_dialog.py
index ac36337..05f5af2 100644
--- a/bouquin/settings_dialog.py
+++ b/bouquin/settings_dialog.py
@@ -69,6 +69,19 @@ class SettingsDialog(QDialog):
 
         form.addRow(theme_group)
 
+        # Add Behaviour
+        behaviour_group = QGroupBox("Behaviour")
+        behaviour_layout = QVBoxLayout(behaviour_group)
+
+        self.move_todos = QCheckBox(
+            "Move yesterday's unchecked TODOs to today on startup"
+        )
+        self.move_todos.setChecked(current_settings.move_todos)
+        self.move_todos.setCursor(Qt.PointingHandCursor)
+
+        behaviour_layout.addWidget(self.move_todos)
+        form.addRow(behaviour_group)
+
         self.path_edit = QLineEdit(str(self._cfg.path))
         self.path_edit.setSizePolicy(QSizePolicy.Expanding, QSizePolicy.Fixed)
         browse_btn = QPushButton("Browse…")
@@ -223,11 +236,13 @@ class SettingsDialog(QDialog):
             selected_theme = Theme.SYSTEM
 
         key_to_save = self.key if self.save_key_btn.isChecked() else ""
+
         self._cfg = DBConfig(
             path=Path(self.path_edit.text()),
             key=key_to_save,
             idle_minutes=self.idle_spin.value(),
             theme=selected_theme.value,
+            move_todos=self.move_todos.isChecked(),
         )
 
         save_db_config(self._cfg)
diff --git a/pyproject.toml b/pyproject.toml
index bcedf1e..301b86d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [tool.poetry]
 name = "bouquin"
-version = "0.1.9"
+version = "0.1.10"
 description = "Bouquin is a simple, opinionated notebook application written in Python, PyQt and SQLCipher."
 authors = ["Miguel Jacq <mig@mig5.net>"]
 readme = "README.md"
diff --git a/tests.sh b/tests.sh
old mode 100644
new mode 100755