Any time you undertake an action where the probable outcome is a quick trip to jail. Jail fails are the second from the bottom in the heirarchy of fails.
See also: Epic fail, death fail
See also: Epic fail, death fail
Steve: So I'm pretty sure I saw you pedipass last night.
Austin: Yeah, I hope it doesn't turn into jail fail.
Austin: Yeah, I hope it doesn't turn into jail fail.
by SargeSmith April 25, 2008
When attempting to Jail Break your ipod, you get to a certain step and fail, giving up all hope of ever doing it.
by Dr. Kremler August 03, 2009
noun. Fail Jail is the zone where one is spiritually sent over the interwebs when they reach an unprecedented level of fail. Also: Faol Gaol, the British version of the term.
Noob 1: Gosh darn golly, I landed on 'Go', that means I get $400 amirite?
Noob 2: This is e-monopoly scrub, there aren't any made up rules. Go directly to FAIL JAIL!!!!11 lul
Noob 2: This is e-monopoly scrub, there aren't any made up rules. Go directly to FAIL JAIL!!!!11 lul
by Cato525 August 03, 2008