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I jailbroke my iPhone 3GS running iOS 5.1.1 three times in a row once.

Took less than a minute each time. The only reason I did it three times was because I didn't realize the first two times I had jailbroken it already. I was expecting a specific response from the program on the computer but not getting it - but the phone was still jailbroken. By the third time I finally figured that out.

Jailbreaking is far easier than it used to be.
 
It took me a little longer this time jail breaking my iPhone 6 plus as I had to dust down my little Samsung Netbook to use windows.
 
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