[ENHANCEMENT] Add Checkpoints in the Orchestrator mode

[mdziekon]

Problem (one or two sentences)

Right now, it is cumbersome to leverage Checkpoints feature from the Orchestrator mode's session view. As far as I can see, there are no Checkpoints created in this mode, however it is possible to reach into a subtask and try to revert from that place. But there are two problems with that: first, there's no easily accessible hierarchical navigation between subtasks (eg. going from parent by selecting specific subtask, and going back to parent from a subtask); and second, restoring from "not last" subtask is probably an error-prone action.

Context (who is affected and when)

Checkpoints in Orchestrator mode could be useful for situations where a subtask has been delegated, but ultimately the developer is not happy with the subtask's result (eg. the implementation is completely borked, and a different approach / prompt is necessary). With Checkpoints in Orchestrator, especially points created right before subtask delegation, it could be possible to restore to a place from before subtask delegation, effectively reverting that subtask's effects.

Desired behavior (conceptual, not technical)

When in Orchestrator mode, and when a subtask is being delegated - create a Checkpoint right before agent starts working on the subtask.

Later on, this Checkpoint should allow restoring both code and session conversation to the state from before the subtask has started.

Constraints / preferences (optional)

• It might be necessary to work on the hierarchical view of tasks first, I believe there's an issue for that already here: [ENHANCEMENT]: Aggregate subtask costs and improve hierarchy visualization in Orchestrator/Boomerang mode #5376 Technically, hierarchical navigation would already be an improvement, therefore this proposal should be considered as "future enhancement request", if that makes sense.
• As far as I can tell, when editing User messages in the Orchestrator mode, it offers a Checkpoint restore, therefore I suspect it should be possible to implement it on a subtask basis as well.

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 explored the codebase. Here is what I found:

Current State

Interestingly, there is already checkpoint logic in place for subtask delegation. In src/core/tools/NewTaskTool.ts:

if (task.enableCheckpoints) {
    task.checkpointSave(true)
}

This code runs right before delegateParentAndOpenChild() is called, meaning a checkpoint should be created before each subtask delegation when checkpoints are enabled.

The force=true parameter (mapped to allowEmpty: true in the checkpoint service) ensures a checkpoint is created even when there are no file changes - which is typically the case in Orchestrator mode since it delegates work rather than modifying files directly.

Potential Issues

Given your report that checkpoints are not appearing in Orchestrator mode, the issue might be:

1. Checkpoint service initialization: The checkpoint service may not be properly initialized for orchestrator tasks since Orchestrator mode has an empty groups: [] configuration
2. Timing issues: The checkpoint save is async but not awaited (task.checkpointSave(true) without await), which could cause race conditions
3. UI visibility: The checkpoint messages might be filtered out in the chat view under certain conditions

Questions

Before proceeding with implementation, I would like to clarify:

1. Verification: Can you confirm that when you run a task in Orchestrator mode with checkpoints enabled (Settings > Checkpoints > Enable), you see NO checkpoint entries in the chat history at all - even when subtasks are delegated?

2. Expected behavior for restoration: When restoring a checkpoint from before a subtask was delegated:

   • Should only the file changes be reverted?
   • Or should the subtask conversation history also be cleaned up/removed?

3. Scope: Given your mention of the hierarchical view issue ([ENHANCEMENT]: Aggregate subtask costs and improve hierarchy visualization in Orchestrator/Boomerang mode #5376), would you like me to focus on:

   • Option A: Just ensuring checkpoints are properly created and visible in Orchestrator mode
   • Option B: Also implementing proper conversation state restoration (removing subtask history when restoring to pre-delegation checkpoint)
   • Option C: Waiting for hierarchical navigation to be implemented first, as you suggested

Please mention @roomote in a comment with your answers, and I will proceed with the implementation plan accordingly.

[mdziekon]

@roomote

1. That's correct, I can't see any checkpoints being presented in the Orchestrator mode. The only way to access that feature directly in the Orchestrator mode is by providing "User messages" somewhere in session, and later on trying to "edit" that message - this way, Roo shows a modal asking the user whether they want to edit just the message, or restore to checkpoint and edit the message.
2. Both, but the behavior should be pickable by the user. This would be similar behavior to "edit message" feature I just mentioned in point 1.
3. Option B, I think.

[roomote]

Thanks for the clarification! I will explore a potential fix that:

1. Makes checkpoint entries visible in the Orchestrator mode chat history (not just through the edit message flow)
2. Implements user-pickable restoration behavior - allowing choice between reverting just file changes vs. also removing subtask conversation history (similar to the edit message modal)

I will open a PR to share progress once I have an implementation ready.

[roomote]

Opened a draft PR (#10624) with my attempt at addressing this issue.

The fix adds await to the checkpoint save before subtask delegation to ensure the checkpoint message appears in the conversation history before the newTask tool block. This makes checkpoints visible in Orchestrator mode when delegating to subtasks.

With this change, users can:

• See checkpoint entries before subtask delegation
• Use "Restore Files" to restore just the file state
• Use "Restore Files and Task" to restore both files AND conversation state (effectively removing the subtask conversation as requested in Option B)

Feedback welcome!