You can see first orange warning "Waiting for the server to restart" - so far OK and expected - and in a while orange warning "Your request time out" - not OK IMHO - and when it disappears the state of server in web console does not change and remains 'This server needs to be restarted' until you hit F and re-navigate to Runtime.
This issue is standalone specific, in domain it works OK.
This issue sometimes happen for 'reload required' as well but for 'restart required' this is permanent flaw.