iTunes Fails Me For the Last Time

I’m back in Iowa for the holidays and getting here was made more painful by a failure of the iTunes DRM machine. We left for the airport on Wednesday morning. Prior to leaving, I signed in to iTunes on my laptop, purchased a movie for Wyatt to watch on the flight, downloaded the movie to my laptop, and then packed up to leave for the airport.
On the plane, as I attempted to play the purchased movie, iTunes informed me that my computer wasn’t authorized and prompted me to sign in, which of course I could not do at 30,000 feet. This is a massive failure of the transactional system that is iTunes. If I purchased a movie on my laptop and subsequently downloaded the movie to my laptop, where else would I want to play it? iTunes was obviously aware that the computer was not authorized. It seems to me that there should have been a prompt to authorize the computer during the purchase process to avoid this scenario.
This will be the last movie I purchase from the iTunes store ever. Some other company can have my money. I need movies that actually work on a plane and it’s obvious I can’t count on iTunes to deliver a reliable experience. Had I ripped the DVD for the same movie (which I also own), I wouldn’t have run into this issue, but then again, that’s deemed illegal.