I've gone in and out of the jailbreak game over the past couple of years: starting with the iPhone 2G, I was tempted by the "dark side" largely thanks to the benefit of unlocking my phone and using another carrier while overseas.
In the end, I simply abanonded jailbreaking as I didn't have the time to regularly check if a jailbreak was available for firmware update X.Y, if it broke anything, if it was tethered or untethered and especially which of the tools (redsn0w, Sn0wBreeze, PwnageTool...) worked flawlessly. Furthermore, about 90% of Cydia's repository (which is the jailbreaking counterpart to Apple's App Store) consisted of trashy UI add-ons, ringtones, games and weird apps that lacked any sort of visual consistency. Still, there was always a set of apps that drew me back...
JailbreakMe 3.0 – The 10-second jailbreak
Once in a while, I like to check up on the jailbreaking community and see what's going on. This is one of these times. JailbreakMe 3.0, released by hacker "comex," is done in seconds and supports all Apple iOS devices running the latest firmware 4.3.3 -- there's no modding the firmware required as it simply uses a vulnerability in the PDF rendering system that Apple hasn't yet patched as of this date (see #3 to fix it yourself, now). It's an easy entrance into the world of jailbeaking.
And despite the fact that Cydia is still cluttered and convoluted, there is that handful of killer applications that will never see the light of day on Apple's App Store and will make you want to jailbreak now.
Obligatory warning: "Hacking" into your iOS device has its pros and cons: Jailbreaking brings its own set of potential risks, such as bricking your device (which I rate as pretty low due to the nature of this jailbreak -- but create a backup nonetheless!) and even voiding warranty (all detailed here), which makes it a no-go for most businesses. Still, there are some very good reasons (for individual users) to jailbreak and make their iPhone, iPad or iPod Touch more useful than ever. Curious? Here are my picks and top reasons to jailbreak your Apple device:
1. Native 3G tethering at no charge: MyWi 4.0
This is an essential tool for the mobile road warrior: MyWi turns your iPad into a mobile hotspot and shares its 3G connection with all WiFi capable devices. When I'm on the go, I simply create a hotspot on my iPad 3G and connect my laptop to it. The developer recently raised MyWi's price to $19.99, but I believe it's still worth the trouble if you're traveling a lot (AT&T users beware, though).
2. Wireless syncing: Don't wait for iOS 5
Wi-Fi Sync lets you sync your iOS device over the air -- a great relief for those hating to run up to a computer and hook up a cable to have all their data up-to-date. It requires a (very small) client running in the background and -- of course -- installing the app via Cydia. (Note: Apple plans to deliver this functionality in iOS 5, slated for release in autumn this year. If you absolutely can't wait and don't mind spending $9 for this comfort, Wi-Fi Sync is your solution.)
3. Patching exploits faster
While jailbreaking itself is a risky process, it also has potential security benefits: usually, Cydia users get security fixes much faster, as was the case with the PDF exploit (which made JailbreakMe 3.0 possible in the first place). The Cydia app "PDF Patcher 2" fixes the vulnerability before Apple has the chance to react.
4. Saving attachments on your iPhone: AttachmentSaver
"Mail.app as it was meant to be" says the description of this little hack: AttachmentSaver ($3) lets you save all attachments (PDF files, Word documents, video clips, etc.) on your iPhone or iPad's storage. So how do you access these files once they're on the device? Easy: install "iFile" to get direct access to your device's file system (see #5).