[BUG] Condense context fails when using Roo Code Router

[mindbound]

Problem (one or two sentences)

On manually invoking context condensation, a 500 internal server error is returned instead of the task being run.

Context (who is affected and when)

Happens to at least in the case of using the Roo Code Router with Claude models.

Reproduction steps

1. Environment: VS Code 1.109.5, Windows 11
2. Actions: Click on the "Intelligently condense context" button in the chat's header
3. Observed: A 500 internal server error instead of the condense task being executed

Expected result

Clicking on the "Intelligently condense context" button in the chat header runs the context condensation task.

Actual result

A "Condensing API call failed: 500 "Internal server error"" error is returned.

Variations tried (optional)

No response

App Version

3.50.5 (961d340)

API Provider (optional)

Not Applicable / Other

Model Used (optional)

claude-sonnet-4.6

Roo Code Task Links (optional)

No response

Relevant logs or errors (optional)

Failed to condense context
Condensing API call failed: 500 "Internal server error"

[roomote]

I've analyzed this issue and here's my proposed implementation plan:

Root cause analysis:

The condensation flow in src/core/condense/index.ts explicitly converts all tool_use and tool_result blocks to plain text representations (lines 310-313) specifically so that the summarization API call does NOT need the tools parameter. The SUMMARY_PROMPT (line 116) also explicitly instructs: "DO NOT call any tools or functions."

However, all three call sites in src/core/task/Task.ts that trigger condensation (condenseContext(), handleContextWindowExceededError(), and the automatic trigger in recursivelyMakeClineRequests) build and pass tool definitions in the metadata:

const metadata: ApiHandlerCreateMessageMetadata = {
    mode,
    taskId: this.taskId,
    ...(allTools.length > 0
        ? { tools: allTools, tool_choice: "auto", parallelToolCalls: true }
        : {}),
}

This means the Roo Code Router proxy receives a request with:

• Messages where all tool blocks have been converted to text (no tool_use/tool_result)
• Tool definitions in the request parameters with tool_choice: "auto"
• A system prompt that says "don't use tools"

This inconsistent combination likely causes the 500 Internal Server Error on the proxy side.

Proposed fix:

1. Remove tools, tool_choice, and parallelToolCalls from the condensation metadata in all three places in Task.ts (lines ~1659-1689, ~3848-3877, ~4060-4093)
2. Simplify each metadata to just { mode, taskId } since tools are unnecessary for summarization
3. Remove the tool-building code blocks (buildNativeToolsArrayWithRestrictions calls) that are only used for the condensation metadata in each of those three methods
4. Update existing tests to verify condensation does NOT include tools in metadata

This change is consistent with the existing design intent expressed in src/core/condense/index.ts (tool blocks already converted to text) and the SUMMARY_PROMPT instruction.

Please mention @roomote in a comment saying that you approve this plan, and I'll proceed with the implementation.