The hardest bug I ever fixed: clean Ctrl+C in an async AI pipeline. When a user presses Ctrl+C during a streaming response with active tool calls, you need to — in order, without race conditions: 1. Cancel the HTTP stream gracefully 2. Abort any in-flight tool executions 3. Clean up temporary state (partial files, temp directories) 4. Preserve conversation history up to the interruption point 5. Return to a clean prompt — ready for the next input Each step can fail. And each failure mode is different. What if Ctrl+C fires between two tool calls? What if the stream buffer hasn't flushed? What if cleanup itself gets interrupted by a second Ctrl+C? What if an async tool call returns after cancellation and tries to write to a closed context? Python's signal handling + asyncio cancellation made it possible. But every edge case took hours to find — because you can only reproduce them by hitting Ctrl+C at exactly the right millisecond. The lesson I keep coming back to: the undo path is always harder than the happy path. And in developer tools, the undo path is what determines whether people trust your software. Stack: Python + Claude API GitHub: https://lnkd.in/ghn_8iKA Full case study: https://lnkd.in/gtg49D-S #Python #Claude #CLI #AsyncPython #Architecture #BuildInPublic #SoftwareEngineering

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