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Our remote debugging session (automatic or manual) currently uses GDB's 'remote' protocol (versus the 'extened-remote' protocol, which we use for remote attaching). With the 'remote' protocol, gdbserver will terminate once the inferior terminates. In this case, if we use the preference to keep GDB alive once the last inferior has terminated, GDB will remain, but gdbserver won't. This means that if the user restarts the inferior, it will be started locally instead of remotely!
I think what we could do is kill GDB when the remote shell exists.