diff --git a/plugins/compound-engineering/.claude-plugin/plugin.json b/plugins/compound-engineering/.claude-plugin/plugin.json
index c14d72b..9cdd11c 100644
--- a/plugins/compound-engineering/.claude-plugin/plugin.json
+++ b/plugins/compound-engineering/.claude-plugin/plugin.json
@@ -1,6 +1,6 @@
 {
   "name": "compound-engineering",
-  "version": "2.26.4",
+  "version": "2.26.5",
   "description": "AI-powered development tools. 27 agents, 21 commands, 14 skills, 1 MCP server for code review, research, design, and workflow automation.",
   "author": {
     "name": "Kieran Klaassen",
diff --git a/plugins/compound-engineering/CHANGELOG.md b/plugins/compound-engineering/CHANGELOG.md
index 996268f..cf75755 100644
--- a/plugins/compound-engineering/CHANGELOG.md
+++ b/plugins/compound-engineering/CHANGELOG.md
@@ -5,6 +5,17 @@ All notable changes to the compound-engineering plugin will be documented in thi
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## [2.26.5] - 2026-01-18
+
+### Changed
+
+- **`/workflows:work` command** - Now marks off checkboxes in plan document as tasks complete
+  - Added step to update original plan file (`[ ]` → `[x]`) after each task
+  - Ensures no checkboxes are left unchecked when work is done
+  - Keeps plan as living document showing progress
+
+---
+
 ## [2.26.4] - 2026-01-15
 
 ### Changed
diff --git a/plugins/compound-engineering/commands/workflows/work.md b/plugins/compound-engineering/commands/workflows/work.md
index 977b0a6..2e9fdf4 100644
--- a/plugins/compound-engineering/commands/workflows/work.md
+++ b/plugins/compound-engineering/commands/workflows/work.md
@@ -76,9 +76,12 @@ This command takes a work document (plan, specification, or todo file) and execu
      - Implement following existing conventions
      - Write tests for new functionality
      - Run tests after changes
-     - Mark task as completed
+     - Mark task as completed in TodoWrite
+     - Mark off the corresponding checkbox in the plan file ([ ] → [x])
    ```
 
+   **IMPORTANT**: Always update the original plan document by checking off completed items. Use the Edit tool to change `- [ ]` to `- [x]` for each task you finish. This keeps the plan as a living document showing progress and ensures no checkboxes are left unchecked.
+
 2. **Follow Existing Patterns**
 
    - The plan should reference similar code - read those files first