Intelligent Context Condensation v2 #10873

hannesrudolph · 2026-01-21T19:42:50Z

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 · 2026-01-21T19:43:20Z

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

src/core/condense/index.ts

src/shared/support-prompt.ts

…ions

…iveApiHistory - Update comment to accurately describe variable content structure (optional command block) - Remove redundant O(n*m) loop that duplicated the .has() check for condenseParent filtering

… simple instruction as system prompt

…clearer sections - Add <analysis> step before summary for structured thinking - Restructure sections for clarity and completeness - Add new sections: 'Errors and fixes', 'All user messages' - Separate 'Pending Tasks' and 'Optional Next Step' sections - Add example output formatting with XML-style tags - Include instructions for handling additional summarization instructions

…oduction Replace task-specific summarization instruction with a more neutral AI assistant prompt that describes the assistant's role for summarization.

- Fix orphan tool_result filtering after fresh start condensation - Add CRITICAL instructions to SUMMARY_PROMPT and CONDENSE template to prevent tool calls during condensing - Inject synthetic tool_results for orphan tool_calls before condensing - Pass tools/metadata to condensation API call - Use standard ErrorRow with Details button for condensation errors - Remove stack trace from error details - Separate summary content into multiple text blocks - Update tests for fresh start model behavior

- Add missing await to this.say() in condenseContext() error path to prevent race conditions with persistence/UI updates - Update comment at line 4075 to accurately reflect that mergeConsecutiveApiMessages() excludes summary messages

The mergeConsecutiveApiMessages function now allows merging a regular user message that follows a summary message. Since this is API-only shaping (storage is unaffected), rewind semantics remain intact. - Remove !prev.isSummary guard to allow merge INTO summary - Keep !msg.isSummary guard to prevent merging a summary INTO something - Update tests to reflect new expected behavior

src/core/condense/index.ts

webview-ui/src/components/chat/context-management/CondensationErrorRow.tsx

src/core/condense/index.ts

Remove unused functions and types that were part of the old condensation model: - getKeepMessagesWithToolBlocks function - KeepMessagesResult type - N_MESSAGES_TO_KEEP constant - hasToolResultBlocks helper - getToolResultBlocks helper - findToolUseBlockById helper - getReasoningBlocks helper These were relics of the old model that kept trailing N messages after the summary. The fresh start model no longer needs them.

- Remove unnecessary JSON encoding in Task.ts when calling say() for condense_context_error - now passes error message directly - Simplify CondensationErrorRow component: remove JSON parsing logic and ErrorRow dependency, just display errorText directly with inline styling - Reduces code complexity while maintaining the same user-facing behavior

roomote · 2026-01-23T06:38:19Z

src/core/task/Task.ts

 			cost,
 			newContextTokens = 0,
 			error,
+			errorDetails,


In Task.condenseContext(), summarizeConversation() returns errorDetails, but the error path drops it and only calls say("condense_context_error", error). This effectively hides the detailed API diagnostics (status/body/stack) that were intentionally captured, making condense failures much harder to debug.

_{Fix it with Roo Code or mention @roomote and request a fix.}

When a user sets a custom condensing prompt, it should control what instructions are sent to the model. Previously, the code used the custom prompt only for the system prompt while the user message content was hardcoded to supportPrompt.default.CONDENSE. Now the custom prompt (or default CONDENSE) is used as the finalRequestMessage content, ensuring user customization is respected. Updated tests to verify the custom prompt appears in the user message.

hannesrudolph · 2026-01-23T06:40:26Z

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.

roomote · 2026-01-23T06:47:19Z

src/core/task/Task.ts

 			cost,
 			newContextTokens = 0,
 			error,
+			errorDetails,


In Task.condenseContext(), summarizeConversation() now returns errorDetails, but the error branch drops it and only displays error. This makes condense failures harder to debug; consider threading errorDetails into the UI payload (e.g., include it in the condense_context_error message so the webview can show/copy it).

_{Fix it with Roo Code or mention @roomote and request a fix.}

github-project-automation bot added this to Roo Code Roadmap Jan 21, 2026

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feat: enhance slash command processing and summary generation in ment…

e1700aa

…ions

fix(condense): update comments and remove redundant loop in getEffect…

defdf0c

…iveApiHistory - Update comment to accurately describe variable content structure (optional command block) - Remove redundant O(n*m) loop that duplicated the .has() check for condenseParent filtering

refactor: swap prompt values - detailed instructions as user message,…

ff6a369

… simple instruction as system prompt

test: update condense tests for swapped prompt values

54f9678

fix(condense): update SUMMARY_PROMPT to use general AI assistant intr…

c96010f

…oduction Replace task-specific summarization instruction with a more neutral AI assistant prompt that describes the assistant's role for summarization.

test(condense): update expectations for condense-rework

b773ddc

test(condense): align condense.spec with condense-rework behavior

fb53935

fix: correct CONDENSE prompt section numbering

b38b961

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Intelligent Context Condensation v2 #10873

Intelligent Context Condensation v2 #10873

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Summary

What Changed

Fresh Start Model

Command Block Preservation

Orphan Tool Result Filtering

Consecutive User Message Merging

Slash Command Help Separation

Improved Error Handling

Restructured CONDENSE Prompt

Breaking Changes

Why This Approach

Dependency Graph

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