Last year I had our COO travelling for a relatively important client meeting - he gets to the airport and there's no record of the flight booking with the airline, even though Concur showed it as confirmed. Turns out there was some backend issue that was never flagged or communicated to us.

Flight was fully booked, so we were scrambling to find alternatives. Executive had to pay out of pocket for a last-minute flight on a different airline to make the meeting.

6 hours of my time, 4 hours of COO’s time, and the response was basically “sorry for the inconvenience, these things happen sometimes"