diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3d4b854..73693b7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,7 @@
+# 0.5.4
+
+ * Ensure pressing enter a second time on a new line with a checkbox, erases the checkbox (if it had no text added to it)
+
 # 0.5.3
 
  * Prevent triple-click select from selecting the list item (e.g checkbox, bullet)
diff --git a/bouquin/markdown_editor.py b/bouquin/markdown_editor.py
index 2d9d9b1..8577cbf 100644
--- a/bouquin/markdown_editor.py
+++ b/bouquin/markdown_editor.py
@@ -1194,7 +1194,7 @@ class MarkdownEditor(QTextEdit):
                     return
                 else:
                     # Not empty - continue the list
-                    self._last_enter_was_empty = False
+                    self._last_enter_was_empty = True
 
                 # Insert newline and continue the list
                 super().keyPressEvent(event)