diff --git a/CLAUDE.md b/CLAUDE.md
index 3122654..f3e18c8 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -86,6 +86,15 @@ src/development_hub/
 | `Ctrl+]` | Expand all sections |
 | `Ctrl+[` | Collapse all sections |
 
+### Dashboard Data Sync
+
+The dashboard automatically syncs data between documentation files:
+
+- **Deliverables → TODOs**: When loading a project dashboard, deliverables from `milestones.md` tables are synced to `todos.md`. If a deliverable doesn't exist as a todo (matched by text + milestone ID), it's added with the appropriate `@M#` tag and priority.
+- **TODOs → Milestone Progress**: The milestone progress bar is calculated from linked todos (items tagged with `@M#`), not from the deliverables table.
+
+This means you can define major work items in milestone deliverable tables, and they'll automatically appear in your todo list for tracking.
+
 ## CLI Scripts
 
 ### `bin/new-project`
diff --git a/src/development_hub/project_list.py b/src/development_hub/project_list.py
index d46a1fc..215127d 100644
--- a/src/development_hub/project_list.py
+++ b/src/development_hub/project_list.py
@@ -14,6 +14,7 @@ from PySide6.QtWidgets import (
     QMenu,
     QMessageBox,
     QProgressBar,
+    QPushButton,
     QTextEdit,
     QVBoxLayout,
     QWidget,
diff --git a/src/development_hub/views/dashboard.py b/src/development_hub/views/dashboard.py
index a94f36f..ec32acf 100644
--- a/src/development_hub/views/dashboard.py
+++ b/src/development_hub/views/dashboard.py
@@ -88,6 +88,7 @@ from development_hub.services.git_service import GitService
 from development_hub.services.health_checker import HealthChecker
 from development_hub.models.health import HealthStatus
 from development_hub.parsers.todos_parser import TodosParser
+from development_hub.models.todo import Todo, TodoList
 from development_hub.parsers.goals_parser import MilestonesParser, GoalsParser
 from development_hub.widgets.progress_bar import MilestoneProgressBar
 from development_hub.widgets.stat_card import StatCardRow
@@ -1107,6 +1108,19 @@ class ProjectDashboard(QWidget):
         if todos_path.exists():
             parser = TodosParser(todos_path)
             todo_list = parser.parse()
+        else:
+            # Create empty TodoList if file doesn't exist
+            todo_list = TodoList(source_file=str(todos_path))
+
+        # Sync deliverables from milestones to todos (adds missing items)
+        if self._milestones_list and todo_list:
+            synced = self._sync_deliverables_to_todos(
+                self._milestones_list, todo_list, todos_path
+            )
+            if synced:
+                # Reload todo_list after sync to get fresh data
+                parser = TodosParser(todos_path)
+                todo_list = parser.parse()
 
         # Create MilestoneWidget for each milestone (keep original file order)
         first_active_shown = False
@@ -3141,6 +3155,81 @@ generated: {datetime.now().strftime('%Y-%m-%d %H:%M:%S')}
         if changed:
             self._save_milestones()
 
+    def _sync_deliverables_to_todos(
+        self, milestones: list, todo_list, todos_path
+    ) -> bool:
+        """Sync milestone deliverables to todos.
+
+        For each deliverable in a milestone, check if a matching todo exists.
+        If not, create a new todo with the appropriate milestone tag and status.
+
+        Args:
+            milestones: List of Milestone objects
+            todo_list: TodoList to add deliverables to
+            todos_path: Path to todos.md for saving
+
+        Returns:
+            True if any todos were added, False otherwise
+        """
+        from development_hub.models.goal import DeliverableStatus
+
+        if not milestones or not todo_list:
+            return False
+
+        added_count = 0
+
+        for milestone in milestones:
+            if not milestone.deliverables:
+                continue
+
+            # Get existing todos for this milestone
+            existing_todos = todo_list.get_by_milestone(milestone.id)
+            existing_texts = {t.text.lower().strip() for t in existing_todos}
+
+            for deliverable in milestone.deliverables:
+                deliverable_text = deliverable.name.strip()
+                deliverable_text_lower = deliverable_text.lower()
+
+                # Check if this deliverable already exists as a todo
+                if deliverable_text_lower in existing_texts:
+                    continue
+
+                # Map deliverable status to todo properties
+                if deliverable.status == DeliverableStatus.DONE:
+                    completed = True
+                    priority = "high"
+                else:
+                    completed = False
+                    # In Progress gets high priority, Not Started gets medium
+                    if deliverable.status == DeliverableStatus.IN_PROGRESS:
+                        priority = "high"
+                    else:
+                        priority = "medium"
+
+                # Create new todo
+                new_todo = Todo(
+                    text=deliverable_text,
+                    completed=completed,
+                    priority=priority,
+                    milestone=milestone.id,
+                )
+
+                # Mark complete with today's date if done
+                if completed:
+                    new_todo.mark_complete()
+
+                todo_list.add_todo(new_todo)
+                added_count += 1
+
+        # Save if any todos were added
+        if added_count > 0 and todos_path:
+            parser = TodosParser(todos_path)
+            parser._frontmatter = parser.frontmatter  # Preserve frontmatter
+            parser.save(todo_list)
+            return True
+
+        return False
+
     def _on_milestone_todo_toggled(self, todo, completed):
         """Handle todo toggle from within milestone widget.