[ENHANCEMENT] Add breakpoints to to-do lists

[IanDaley]

Problem (one or two sentences)

It would be handy to be able to put a breaklist on to-do lists so when using auto-approve it would still stop when that item was arrived at on the to-do list. This means Roo could be set on auto pilot up to a point such as implementing the back end, with a break point set before it start on the front end to allow for manual verification.

Context (who is affected and when)

This would be beneficial to many users who use Auto Approve but want to set arbitrary check points to stop it rolling full steam into the next task - if the user wants to have logical break points for verification.

Desired behavior (conceptual, not technical)

When a todo list is visible a user could click on an icon to set a breakpoint
when the orchestrator or other mode encounters this breakpoint as it works through a to-do list it stops waiting for user interaction

Constraints / preferences (optional)

No response

Request checklist

• I've searched existing Issues and Discussions for duplicates
• This describes a specific problem with clear context and impact

Roo Code Task Links (optional)

No response

Acceptance criteria (optional)

No response

Proposed approach (optional)

No response

Trade-offs / risks (optional)

No response

[roomote]

I have analyzed this issue and here is my proposed implementation plan:

Overview

Add a breakpoint feature to todo list items that pauses auto-approve mode when reached.

Proposed Changes

1. Extend TodoItem Schema (packages/types/src/todo.ts)

Add an optional breakpoint boolean field to the TodoItem type:

export const todoItemSchema = z.object({
  id: z.string(),
  content: z.string(),
  status: todoStatusSchema,
  breakpoint: z.boolean().optional(), // NEW: When true, auto-approve pauses at this item
})

2. Update TodoListDisplay UI (webview-ui/src/components/chat/TodoListDisplay.tsx)

• Add a breakpoint icon (e.g., Circle or OctagonAlert from lucide-react) next to each todo item
• When expanded, users can click the breakpoint icon to toggle the breakpoint state
• Visual indicator (e.g., red dot/icon) when breakpoint is active
• Send a message to the extension when breakpoint is toggled

3. Update Auto-Approval Logic (src/core/auto-approval/index.ts)

• Before auto-approving any tool action, check if the current in-progress todo has a breakpoint
• If a breakpoint is detected on the current todo, return { decision: "ask" } to pause auto-approve
• This will require access to the current task state/todo list

4. Update UpdateTodoListTool (src/core/tools/UpdateTodoListTool.ts)

• Parse and preserve the breakpoint property when updating todos
• Update markdown parsing to optionally support breakpoint notation (e.g., [!] prefix or special marker)

5. Add Webview Message Handler

• Add a new message type for toggling breakpoints
• Handle the message in webviewMessageHandler.ts to update the todo item

Benefits

• Users can set arbitrary checkpoints for verification during long auto-approve sessions
• Non-intrusive: breakpoints are optional and do not affect normal workflow
• Works with existing auto-approve infrastructure

Questions/Considerations

1. Should breakpoints persist across sessions (saved in task history)?
2. Should there be a visual notification when auto-approve pauses due to a breakpoint?
3. Should breakpoints be configurable via markdown syntax (e.g., [!] Task with breakpoint) or only via UI clicks?

Please mention @roomote in a comment saying that you approve this plan (or provide feedback), and I will proceed with the implementation.

[IanDaley]

Personally I don't think they should persist across sessions because basically they're disposable. Once they're hit they no longer serve any purpose.

It should just make the same 'finished' sound notification sound it makes now when a task is complete.