What is Jaily?
1.
To do something morally or ethically wrong, something that might result in jail time.
"Man, Steve got himself into some real jaily shit last night."
See
2.
Adjective. Descriptive of any illegal act of sufficient gravity that the perpetrator runs the risk of jail time; drunk driving, armed robbery, murder, possession with intent to distribute, etc.
"Knock over the Kwik-E-Mart? I dunno dude, that's pretty jaily."
See