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1. jailbreak
to crack an iPhone so it can run 3rd party programs. just like how you were able to install other programs w/PSP
noob: dude, u gotta update your iPhone, the new patch is awesome
guy: screw that, I'm waiting for someone to jailbreak the new patch so I can run my games
2. jailbreak
In electronics: to enable use of a consumer electronics product not intended by the manufacturer through the exploitation of software hacks.

Commonly used to refer to enabling a carrier-locked phone, such as the iPhone, to accept SIM cards from other carriers. Or a restricted platform to run unlicensed or homebrew software.
"If you don't want to pay for AT&T on your iPhone, you can just jailbreak it."
3. Jailbreak
When your penis dangles down one of your legs and partly exists outside of your underwear. Never happens when wearing tight pants.
"Yo dude, look away. I've got to put my hand in and stop a jailbreak.
4. jailbreak
the time immediately after leaving a long term relationship when you rediscover your freedom and have sex with as many people as you can
he only just broke up with her and already he's shagged 4 other girls

oh he's just on a jailbreak
5. Jailbreak
Usually occurs while farting or "break"ing wind. During a windbreak a small unassuming turd seizes the opportunity and sneeks out while the door is open (so to speak).
I can't believe it, but I was out crop dusting in the hallway yesterday and had a jailbreak, so I had to visit the restroom for a cleanup on aisle 5.
6. jailbreak
The rare and exciting occurrence when one or both of a woman's breasts pop out of the bra accidentally and are exposed for all to see.
Woah! Jailbreak! Nice titty.

or

Dude, did you catch that near jailbreak?
Yeah, I definitely saw a bit of a nipple.
7. jailbreak
To unlock a cell phone from its service provider so that it can be used with other SIM cards from different companies.
To unlock an iphone from AT&T and make it a free bird. Just shove in any GSM tri-band SIM card and you are good to go! thats what you call jailbreak
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