[PierrunoYT]

Related GitHub Issue

Closes: #1774

Complements #1705 (for #1307), which fixes how new user messages are built.

Description

When read_file on an image runs alongside another tool call in the same turn, the next user message can be saved as [tool_result, image, tool_result, text]. Anthropic requires the results for the previous turn's tool_use blocks to lead the message, so the request fails with a 400. Because the broken message is already in api_conversation_history.json, every retry sends it again and the task stays stuck.

#1705 stops new messages from being built with that shape. It does not repair history that was already saved with it, which is the retry problem #1774 also reports. This PR covers that part:

• orderToolResultsFirst (src/core/task/orderToolResultsFirst.ts) moves each user message's tool_result blocks to the front. It keeps the order of the results and of the remaining blocks, and returns messages that are already in order unchanged.
• Where it runs: in attemptApiRequest, right after mergeConsecutiveApiMessages, because merging consecutive user messages can interleave blocks too. It only shapes the request; stored history is not modified, the same as the merge step.
• Effect: a task already stuck with the broken shape recovers on its next retry, with no manual editing of api_conversation_history.json.
• Other providers: moving images and text after the results keeps their meaning for the other providers too. The OpenAI-format conversion already splits tool_result blocks into separate tool messages.

The two PRs don't overlap: #1705 changes Task.pushToolResultToUserContent, and this changes request shaping. Either can merge first.

Test Procedure

• orderToolResultsFirst.spec.ts covers:
  • the exact persisted [BUG] Image read_file combined with other tool calls produces Anthropic 400 error #1774 shape (stored message left unchanged);
  • several interleaved images;
  • interleaving created by mergeConsecutiveApiMessages;
  • already-ordered, string, and assistant messages returned as the same object.
• Task.spec.ts: a new test goes through the real attemptApiRequest with the [BUG] Image read_file combined with other tool calls produces Anthropic 400 error #1774 history. It asserts that the request sent to createMessage leads with both tool_result blocks, and that stored history keeps its shape. The test fails without the change to Task.ts.

cd src
npx vitest run core/task core/assistant-message

Results: 47 files / 681 tests passed; type checking and ESLint passed (also via the commit hook). ESLint suppression counts are unchanged.

Pre-Submission Checklist

• Issue Linked: This PR is linked to an approved GitHub Issue (see "Related GitHub Issue" above).
• Scope: My changes are focused on the linked issue (one major feature/fix per PR).
• Self-Review: I have performed a thorough self-review of my code.
• Testing: New and/or updated tests have been added to cover my changes (if applicable).
• Visual Snapshot (UI changes only): Not applicable; no UI changes.
• Documentation Impact: I have considered if my changes require documentation updates (see "Documentation Updates" section below).
• Contribution Guidelines: I have read and agree to the Contributor Guidelines.

Visual Snapshots

Not applicable; no UI changes.

Videos (interaction / animation only)

Not applicable.

Documentation Updates

• No documentation updates are required.

Additional Notes

No live Anthropic request was made; the tests assert the request payload handed to createMessage.

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2953-2962: LGTM!

Also applies to: 2998-3003

📝 Summary

Summary by CodeRabbit

• Bug Fixes
  • Improved the ordering of tool results when conversation history is prepared for processing. Tool results are now placed before other content in the same user message, while the conversation’s original order remains unchanged for display and storage. This helps ensure mixed content, such as images and environment details, is handled consistently alongside tool results.

Task now reorders tool-result blocks ahead of other content in merged user messages before passing API history to createMessage. Stored conversation history retains its original block order.

Changes: Tool-result ordering

Layer / File(s)	Summary
Reorder interleaved tool results src/core/task/orderToolResultsFirst.ts, src/core/task/__tests__/orderToolResultsFirst.spec.ts	The helper moves tool-result blocks before other blocks in user messages with array content. It preserves order within both groups and leaves unchanged or unsupported message shapes unchanged. Tests cover ordering, timestamps, input preservation, and unchanged-message references.
Apply ordering to API history src/core/task/Task.ts, src/core/task/__tests__/Task.spec.ts	Task applies the helper after merging consecutive user messages. The regression test checks that API history starts with both tool results and that stored history retains its original order.

Priority: ➖ Normal

Estimated code review effort: 2 (Simple) | ~10 minutes

Change: Bug fix · Severity of issue fixed: Medium

Merge Risk: ⚪ Minimal · up to 47e96

No actionable merge-blocking risk remains from the reviewed changes.

Caution

Pre-merge checks failed

Please resolve all errors before merging. Addressing warnings is optional.

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Failed checks: 1 error

Check name	Status	Explanation	Resolution
Linked Issues check		#1774 requires the image from read_file to be nested in the corresponding tool_result.content. orderToolResultsFirst only moves standalone image blocks after all tool_result blocks. The imag…	Associate each standalone image with its corresponding read_file tool_result and place it in that result's content array during request shaping. Add or update an integration test that verifies the Anthropic payload and preserves store…

Passed checks: 7 passed

Check name	Status	Explanation
Title check		The title clearly and concisely describes the main change: placing tool-result blocks first in request user messages.
Description check		The description covers the linked issue, implementation, scope, testing procedure, results, checklist, documentation impact, and additional notes. The required Get in Touch section with a Discord user…
Out of Scope Changes check		The production change is limited to API request shaping for the malformed tool-result ordering in #1774. The unit and integration tests verify ordering, merged messages, retry behavior, and unchanged …
Regression Evidence		Focused coverage is present for the changed request shaping. orderToolResultsFirst.spec.ts covers persisted interleaving, multiple result/image interleavings, merge-created interleaving, ordering pr…
Security Boundaries		No changed path meets the security failure conditions. src/core/task/orderToolResultsFirst.ts:14-32 only reorders existing user message blocks and does not execute or interpret their contents. `src/…
Persistence Integrity		No changed persistence path exists. The pull request adds request-only shaping in attemptApiRequest and orderToolResultsFirst; neither writes apiConversationHistory or task storage. The helper c…
Lifecycle Resource Cleanup		No changed lifecycle path can leak a resource or duplicate work. The new orderToolResultsFirst function is a synchronous, pure array transformation with no listeners, watchers, timers, providers, ta…

Full details: Description check

Explanation

The description covers the linked issue, implementation, scope, testing procedure, results, checklist, documentation impact, and additional notes. The required Get in Touch section with a Discord username is missing, but the description is otherwise complete.

Full details: Out of Scope Changes check

Explanation

The production change is limited to API request shaping for the malformed tool-result ordering in #1774. The unit and integration tests verify ordering, merged messages, retry behavior, and unchanged stored history. No unrelated production behavior is shown.

Full details: Regression Evidence

Explanation

Focused coverage is present for the changed request shaping. orderToolResultsFirst.spec.ts covers persisted interleaving, multiple result/image interleavings, merge-created interleaving, ordering preservation, no-result content, string content, assistant messages, unchanged references, and storage immutability. Task.spec.ts verifies the real attemptApiRequest sends reordered results and leaves stored history unchanged. The PR changes only task logic and tests, so no Playwright snapshot is required.

Full details: Security Boundaries

Explanation

No changed path meets the security failure conditions. src/core/task/orderToolResultsFirst.ts:14-32 only reorders existing user message blocks and does not execute or interpret their contents. src/core/task/Task.ts:5844-5857 applies this transformation to the API request copy before createMessage; it does not modify stored history or approval and tool-policy controls. No secret/PII leak, unvalidated execution path, or approval/allowlist bypass is introduced.

Full details: Persistence Integrity

Explanation

No changed persistence path exists. The pull request adds request-only shaping in attemptApiRequest and orderToolResultsFirst; neither writes apiConversationHistory or task storage. The helper creates a new reordered message and leaves stored message content unchanged. The added Task.spec.ts test also verifies the stored history keeps its original block order.

Full details: Lifecycle Resource Cleanup

Explanation

No changed lifecycle path can leak a resource or duplicate work. The new orderToolResultsFirst function is a synchronous, pure array transformation with no listeners, watchers, timers, providers, tasks, or cancellation callbacks. Task.attemptApiRequest calls it only during request shaping, and the existing beginApiWork() cleanup remains guarded by finally.

Full details: Linked Issues check

Explanation

#1774 requires the image from read_file to be nested in the corresponding tool_result.content. orderToolResultsFirst only moves standalone image blocks after all tool_result blocks. The image remains a top-level sibling, so the PR does not implement the requested message shape. The retry request-shaping behavior is covered by Task.ts and the reported tests.

Resolution

Associate each standalone image with its corresponding read_file tool_result and place it in that result's content array during request shaping. Add or update an integration test that verifies the Anthropic payload and preserves stored history.

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Inline comments:
Review comments at @src/core/task/__tests__/Task.spec.ts:
- Around line 2988-2992: Update the test assertions around lastUserContent to
verify the complete outgoing user content, not just the leading tool_result
blocks: use an image-capable mock handler and assert that the image and trailing
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🪛 GitHub Check: mutation-diff

src/core/task/orderToolResultsFirst.ts

[warning] 21-21: Mutation test advisory
src/core/task/orderToolResultsFirst.ts:21: Survived ConditionalExpression mutant (replacement: true). See the job summary for the complete list and resolution guidance.

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[warning] 16-16: Mutation test advisory
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