An underground group of programmers known as the Dev Team, for the most part, spearheads all this jailbreak technology more or less without Apple’s permission. Think of the Dev Team as the LA SWAT team with huge awesome guns trying to get into a barricaded building, which is the jailbroken iPhone software.
Every time they find a way in, Apple comes along and puts another barricade up with a software update that closes the entrance they had. Then they have to find another way in. They are currently working on jailbreaks for 3GS and iPod Touch software version 3.1.3, so if you upgrade to the newest version of the firmware, you will lose the ability to jailbreak at this time.
So it’s just a best practice to check the latest firmware version jailbroken (see the Dev Team blog) versus your own (go to Settings > General > Status). Aside from the above mentioned risks, there’s always the chance of your iPhone “bricking” or getting stuck in a non working state.
Several times during jailbreaks, mine would be stuck in phone purgatory for hours. Take just a few moments to browse any iPhone forum with jailbreaking topics and you’re sure to find several comments along the lines of “help! I tried to jailbreak my iPhone and now it’s been stuck on the Apple logo for hours, help!” or “Please help me, after jailbreaking my iPhone my GPS won’t work.”
So things definitely can go wrong, but generally it’s user error. Usually plugging in your iPhone to your computer, starting iTunes, and holding power for 5 seconds, power and menu button for 10 seconds, and then just menu for 20 seconds, tells iTunes your phones fried and it will do a fresh install of your most recent iPhone software. For more information on getting your iPhone out of the constant reboot cycle, read this article.
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