[BUG] Context Condensing Initial Prompt Preservation Should Be Optional

[enerage]

Context condensing currently always preserves/includes the initial prompt in the condensed context. This causes RooCode to restart previously completed tasks when they get reintroduced through the preserved initial prompt.

Impact
Tasks that were already resolved are being restarted after context condensing
This creates unnecessary work and potential confusion in the workflow
Users have no control over this behavior

Proposed Solution
Make initial prompt preservation conditional on the experimental power-steering feature being enabled. This would:

Give users control over whether they want this behavior
Prevent task restarts for users who don't need the preservation feature
Maintain backward compatibility for existing workflows

Issue reported on: September 17, 2025
This behavior change was introduced recently
Affects task management and workflow efficiency

Context (who is affected and when)

All users

Reproduction steps

Complete a task in RooCode
Trigger context condensing
Observe that the initial prompt is preserved in condensed context
Note that RooCode attempts to restart the previously completed task

Expected result

Initial prompt preservation should only occur when power-steering is explicitly enabled by the user.

Actual result

Initial prompt is always preserved during context condensing, regardless of user preferences.

Variations tried (optional)

No response

App Version

3.28.3

API Provider (optional)

OpenAI

Model Used (optional)

GPT5-High-Codex

Roo Code Task Links (optional)

No response

Relevant logs or errors (optional)

[roomote]

I'm exploring a potential fix for this issue where context condensing always preserves the initial prompt. I'll work on making this behavior conditional on the power-steering feature being enabled, which should prevent tasks from being restarted unnecessarily.

[roomote]

I've created PR #8094 to address this issue: #8094

The fix makes initial prompt preservation conditional on the power-steering experimental feature being enabled. This prevents tasks from being restarted unnecessarily after context condensing when power steering is disabled.

All tests are passing and CI checks have completed successfully. The implementation:

• Adds a powerSteeringEnabled parameter to the summarizeConversation function
• Only preserves the first message when power steering is enabled
• Updates all callers to check and pass the power steering state

This should resolve the issue where previously completed tasks were being restarted due to the preserved initial prompt being reintroduced after context condensing.

[daniel-lxs]

Hey @enerage, we believe that the condensing feature should not remove the first message because it contains crucial information/instructions for the task itself. We have noticed that if you use a single task for multiple things, then condensing might trigger the original instructions again. I think the best solution would be to change the condensing prompt so it lets the model know that the task has progressed past the first user message.

I'll close this issue but let me know if you have any thoughts!