Intelligent Context Condensation v2

[hannesrudolph]

Summary

This PR implements a "Fresh Start Model" for context condensation - a fundamental architectural change where summary messages transition from assistant role to user role. This simplifies the condensation architecture by eliminating several workarounds while introducing targeted mechanisms for command preservation and orphan cleanup.

What Changed

Fresh Start Model

The core change: summary messages now have role: "user" instead of role: "assistant".

Before:

• Summary was an assistant message inserted before kept messages
• Required synthetic reasoning blocks for DeepSeek-reasoner compatibility
• Preserved tool_use blocks to maintain pairing with subsequent tool_results
• Kept trailing N messages after summary

After:

• Effective API history contains only the summary (true fresh start) after a condensing event
• Summary is a user message placed at the end of message history
• No reasoning blocks needed (user messages don't require them)
• No tool_use preservation needed

Command Block Preservation

New extractCommandBlocks() function extracts <command> XML blocks from the original task and injects them into summaries wrapped in <system-reminder> tags. This ensures workflow directives (like /prr #123) survive multiple condensation cycles.

Orphan Tool Result Filtering

getEffectiveApiHistory() now filters orphan tool_result blocks that reference tool_use IDs from condensed-away messages. This prevents API validation errors that would occur when tool_result blocks have no matching tool_use.

Consecutive User Message Merging

New mergeConsecutiveApiMessages() utility non-destructively merges consecutive user messages for API requests only. This handles the case where a user summary followed by a user message would create invalid consecutive same-role messages.

Slash Command Help Separation

parseMentions() now returns slashCommandHelp separately from the main text. This allows selective extraction of command blocks during condensation while keeping the user's actual message content clean.

Improved Error Handling

• Error details now include both message and details fields (JSON structure)
• CondensationErrorRow uses shared ErrorRow component with copy functionality
• New i18n string condense_api_failed for API error messages

Restructured CONDENSE Prompt

Completely rewritten with a highly structured XML format:

<summary>
1. Primary Request and Intent
2. Key Technical Concepts
3. Files and Code Sections (with snippets)
4. Errors and fixes (with user feedback)
5. Problem Solving
6. All user messages (non-tool-result)
7. Pending Tasks
8. Current Work (precise description)
9. Optional Next Step
</summary>

Breaking Changes

• Summary messages now have role: "user" instead of role: "assistant"
• Effective API history after condensation contains only the summary (no trailing messages)
• N_MESSAGES_TO_KEEP constant removed
• Summary timestamp now uses lastMsgTs + 1 instead of firstKeptTs - 1

Why This Approach

Problem	Solution
DeepSeek reasoning requirement forced complex assistant summaries	User role doesn't need reasoning blocks
Tool_use/tool_result pairing complex across condensations	User summaries don't need tool_use; orphan cleanup handles residuals
Workflow directives lost after condensation	extractCommandBlocks() preserves <command> blocks
Consecutive user messages cause API errors	mergeConsecutiveApiMessages() for API requests only
Important information lost during summarization	Highly structured prompt with explicit sections
Error details not copyable	JSON structure with ErrorRow component integration

Dependency Graph

Fresh Start Model (summary = user role)
       │
       ├── No reasoning blocks needed
       ├── No tool_use preservation needed
       │
       ├── extractCommandBlocks() → Preserves workflow directives
       │
       ├── getEffectiveApiHistory() → Orphan tool_result filtering
       │
       ├── mergeConsecutiveApiMessages() → Handles consecutive user messages
       │
       ├── slashCommandHelp separation → Enables command extraction
       │
       ├── Structured CONDENSE prompt → Better information preservation
       │
       └── JSON error structure → ErrorRow component integration

---

Important

Transition summary messages from assistant to user role for context condensation, simplifying architecture and improving functionality.

• Behavior:
  • Summary messages now have role: "user" instead of role: "assistant".
  • Effective API history contains only the summary after a condensing event.
  • New extractCommandBlocks() function to preserve <command> blocks in summaries.
  • getEffectiveApiHistory() filters orphan tool_result blocks.
  • mergeConsecutiveApiMessages() utility merges consecutive user messages for API requests.
• Tests:
  • Updates to condense.spec.ts and index.spec.ts to reflect new behavior.
  • New tests for extractCommandBlocks() and mergeConsecutiveApiMessages().
• Misc:
  • N_MESSAGES_TO_KEEP constant removed.
  • Summary timestamp now uses lastMsgTs + 1 instead of firstKeptTs - 1.

^{This description was created by for 7a361ae. You can customize this summary. It will automatically update as commits are pushed.}

[roomote]

Oroocle   Follow along on Roo Cloud

Re-review in progress for 7a361ae5b4e69a6a74f07489684d34e4a36e507d.

• Fix CONDENSE support prompt section numbering: previously "6." appeared twice (All user messages vs Pending Tasks).
• Condense: finalRequestMessage.content ignores customCondensingPrompt (custom prompt not actually sent as the summarization request content).
• Condense: summarizeConversation() returns errorDetails, but Task.condenseContext() drops it from the UI error path (fix-id: ab3a636175).

Previous reviews

• 25a4e2f: Review #1
• b95584e: Review #2
• 757dfcf: Review #3
• 41f43bc: Review #4
• 757dfcf: Review #5
• 32e7ab5: Review #6
• 16296c8: Review #7
• 16296c8: Review #8
• bc8c81f: Review #9
• a9871c7: Review #10
• 307d0a5: Review #11
• 8529156: Review #12
• dca5f66: Review #13
• f56bced: Review #14
• a64318e: Review #15
• a654a9a: Review #16
• 17d6649: Review #17
• 6a47719: Review #18
• 5577d17: Review #19
• cbf6eda: Review #20
• 06f2a8b: Review #21
• 9ea6b3f: Review #22
• bb3fb35: Review #23
• 859fb14: Review #24
• c0fa042: Review #25

_{Mention @roomote in a comment to request specific changes to this pull request or fix all unresolved issues.}

[roomote]

Summary

• Condense is now non-destructive: older messages are tagged with condenseParent and filtered via getEffectiveApiHistory(), while rewind/edit semantics keep the original message boundaries.
• New API-only shaping merges consecutive user turns via mergeConsecutiveApiMessages() to reduce token overhead without mutating stored history.
• Slash-command mention parsing now returns slashCommandHelp separately and processUserContentMentions() appends it as a dedicated text block (instead of mixing it into the main user text).

Tested

• cd src && npx vitest run core/task/tests/mergeConsecutiveApiMessages.spec.ts core/condense/tests/condense.spec.ts core/condense/tests/index.spec.ts core/condense/tests/rewind-after-condense.spec.ts core/mentions/tests/processUserContentMentions.spec.ts tests/command-mentions.spec.ts core/webview/tests/webviewMessageHandler.delete.spec.ts
• cd apps/web-roo-code && npm run lint && npm run check-types
• cd apps/web-evals && npm run lint && npm run check-types && npx vitest run

[hannesrudolph]

Yes, this was an unintentional bug. I've pushed a fix (commit 7a361ae) that now properly uses the customCondensingPrompt (or defaults to supportPrompt.default.CONDENSE) for the user message content. This ensures user customization is respected when they set a custom condensing prompt.

Before: The custom prompt was only used for the system prompt, while the user message was hardcoded to supportPrompt.default.CONDENSE.

After: The custom prompt (or default) is now used as the finalRequestMessage.content, so users can fully customize the summarization instructions sent to the model.