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
Steve: So I'm pretty sure I saw you pedipass last night.
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.
Uh, I got stuck on the recovery phase.. Jail fail.. :(
by Dr. Kremler August 03, 2009

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