The most tragic goof from the airline's standpoint seems to be the "you may check in online" email, implicitly confirming the 2nd leg was still on. I'm guessin

The most tragic goof from the airline's standpoint seems to be the "you may check in online" email, implicitly confirming the 2nd leg was still on. I'm guessing the moment he booked his flight, a script somewhere inserted two rows into a database, and a daily cron slurped up each one to send the automated emails. So few people miss the first legs these days that they haven't bothered to make the "cancel entire itinerary" cron stop the return leg email from sending. I still think that complaining to customer service might get him a flight voucher if he plays his cards properly.