After context compaction, the preserved last assistant message retained
its structured tool_calls field, but the corresponding tool_result was
summarized away. This created orphaned tool_use blocks that violated
the Anthropic API constraint: 'Each tool_use block must have a
corresponding tool_result block in the next message', causing 400 errors.
Primary fix: clear tool_calls from the preserved assistant message in
extract_preserved_messages(). The tool call was already executed and
its result is captured in the summary.
Defense-in-depth: added strip_orphaned_tool_use() post-processing in
Anthropic convert_messages() to detect and strip any orphaned tool_use
blocks before they reach the API.
Added 7 tests: 3 unit tests for compaction stripping, 3 unit tests for
Anthropic orphan detection, 1 integration test reproducing the exact
bug scenario from the h3 session.
The previous implementation added the summary as a System message, which
caused "Conversation must start with a user message" errors because the
first non-system message after compaction was Assistant (the preserved
last assistant message).
Fix: Change summary from System to User message, creating valid alternation:
[System Prompt] -> [Summary as USER] -> [Last Assistant] -> [Latest User]
This also prevents system message bloat across multiple compactions since
the summary is now part of the conversation flow and gets replaced on
each compaction.
Added test_second_compaction_no_bloat to verify no accumulation.
When context window compaction occurs, the last assistant message is now
preserved in addition to the system prompt, README, and summary. This
improves continuity after compaction by keeping the LLM's most recent
response, which often contains important context about what was just
done or what comes next.
New message order after compaction:
[System Prompt] -> [README/AGENTS.md] -> [ACD Stub?] -> [Summary] -> [Last Assistant] -> [Latest User?]
Changes:
- Add last_assistant_message field to PreservedMessages struct
- Modify extract_preserved_messages() to find last assistant message
- Modify reset_with_summary_and_stub() to include last assistant message
- Add comprehensive integration tests using MockProvider
Tests cover edge cases:
- No assistant message exists
- Tool-call-only assistant messages (still preserved)
- Multiple assistant messages (only last one preserved)
- No trailing user message
