A paradoxical situation that has no happy ending. A popular movie with Alan Arkin in 1970, Catch-22 came from Joseph Heller's 1961 comical, yet gruesome, best-selling book about pilots in a fictitious World War II setting. The paradox was that no sane pilot would be crazy enough to want to continue flying dangerous missions. The only way a pilot would be grounded is if he were truly crazy, but if he asked to be grounded, he was then considered sane and would not be grounded.

A Catch-22 with software would be trying to install a new version of the OS that conflicts with the current display driver. Although a new version of the display driver may be available for the new version of the OS, the current display driver does not allow the new OS to be installed. Sometimes, a Catch-22 is used synonymously with a "chicken-egg" dilemma (which comes first?), but it is more accurately a conundrum without a winning solution.