A new issue (depending on this one and potentially on issue 31388) would be helpful, especially if you were able to use the testing trace hook from this PR to reproduce the problem.

The reason I've taken the async with change out of this issue is because it's untestable given the current state of asyncio - the pending call fires as soon as the YIELD_FROM opcode is reached and control returns to the asyncio event loop. If there's a simple(ish) coroutine driver we can add to manage KeyboardInterrupt adequately for testing purposes, I'd be prepared to do that, but I'd still like to consider the async case separately from the synchronous one.