Some years ago I was associated with an airline that some might refer to as "Blue Paranoia", a new Captain was joining and needed a flight booking from FRA to FCO, "Paranoia" didn't trust me to book flights (and recharge) so their secretarial staff, bless them, booked this Captain something like a 6am departure from Frankfurt/Hahn
I didn't have too much time for this Captain, indeed he didn't last in the job very long, so I saw the amusing side of picturing him getting from Frankfurt to Hahn at something like 2am, but thereafter "Paranoia" and myself, at a meeting, agreed that I would do the flight bookings in the future.