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Addresses the issue of parallel tool approvals freezing Assistant and causing UX ambiguity around what happens if only part of multiple dependent invocations is approved. Two layers at which this is addressed: 1. Tightens prompt to clarify approval tools must be issued one per step, not in parallel. 2. In case something slips past the prompt, this also auto-denies all but the first `approval-required` tool call when the model issues multiple in the same step, so the model is forced to reissue them sequentially. **Demo** The following chats demo me explicitly asking Assistant to run those approval-gated tools in parallel, and the Assistant correctly invokes them sequentially instead. | Parallel `execute_sql` request | Parallel `deploy_edge_function` request | |--------|--------| | <img width="1820" height="4240" alt="CleanShot 2026-06-16 at 16 20 23@2x" src="https://github.com/user-attachments/assets/3ddad61d-24d6-4e5b-8572-c261755f3a03" /> | <img width="1738" height="2726" alt="CleanShot 2026-06-16 at 16 22 59@2x" src="https://github.com/user-attachments/assets/77a0aa20-e3cb-4061-b270-ab2a96d1e64a" /> | As shown in [this trace](https://www.braintrust.dev/app/supabase.io/p/Assistant/trace?object_type=project_logs&object_id=5a8d02e5-b3b6-40cc-ba76-ecee286478f4&r=a3a37857-95df-4a95-a5a8-818ea305b2a5&s=a3a37857-95df-4a95-a5a8-818ea305b2a5), parallel tool calls are still allowed for context gathering tools that don't require approval: <img width="1051" height="517" alt="CleanShot 2026-06-16 at 16 25 42@2x" src="https://github.com/user-attachments/assets/00d208b1-6131-4b8e-910e-e92fd2a79a5b" /> Closes AI-803 <!-- This is an auto-generated comment: release notes by coderabbit.ai --> ## Summary by CodeRabbit * **Improvements** * Approval-required operations are now processed sequentially rather than in parallel within the AI Assistant. * **Tests** * Added comprehensive test coverage for the parallel approval prevention logic. <!-- end of auto-generated comment: release notes by coderabbit.ai -->