You'll notice
A redelivered permission or dialog request is re-armed when it matches the one originally shown, instead of being dropped.
RemoteSessionManager gains a rearmRedelivered path: when a can_use_tool or request_user_dialog control request is redelivered after being retired, it checks whether the redelivered request matches the request originally shown under that id, and if so re-arms it instead of dropping it. Mismatches are flagged with telemetry rather than being silently kept.