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jailbreak 

The act of stealing your phone back from your parents after they have "confiscated" it because you went over on texts or minutes.
"Hey text me later about saturday!" Krista
"Sure, oh shit I forgot my parents took my phone! I'll have to jailbreak it!"
jailbreak by lucy=D August 9, 2008

jailbreak 

making your ios device pwned because you didnt buy an android and you're pissed about it
i did a jailbreak on my ipad and now everything broke but hey it works like an android right?!
jailbreak by a big potato man March 17, 2020

Jailbreak 

a stupid copy of Prison Break with a bigger Map size. you can rob a bank without any security man, a jewelery without a salesman, a factory that is abadoned but somehow still working, a cargo train and the freking polar express.
Do you know the Game Jailbreak that copied Prison Break
Jailbreak by GT FIRΞ May 17, 2020

Jailbreak 

(noun) – Taking a “break” from smoking weed every day by drinking heavily for no more than three days in a row—technically off weed, but not really giving your body a reset.
“Hey man, you want a hit?”
*slurs sentence* “Sorry brother, I can’tI’m on a jailbreak.”
Jailbreak by TJ69420SWAG March 3, 2025

Jailbreak 

Oh shit, that pedophile hunter guy jailbroke the AI!
Hym "See!? I told you they would start to jailbreak it and and that's when shit would go off the rails... I'M LIKE A SEER! LIKE THE SUPREME FORTUNE TELLER OF OUR TIME!"
Jailbreak by Hym Iam April 27, 2025

Jailbreak Discord 

Man1: "Hey man are you in the Jailbreak Discord"

Man2: "hell no man last time i joined that i lost braincells"
Jailbreak Discord by i_pp_my_pants February 17, 2019