Okay, I took a few attempts to understand this, so I’ve typed it all out in a “For village idiots” style tutorial to hopefully help anybody having the problems I was having.

I’m trying to Jailbreak my new iPhone 3GS with the BlackRa1n Jailbreak application. But I keep getting stuck on the Connect to iTunes logo when the phone reboots. iTunes then tells me that the phone is in recovery mode and will need to be restored to factory default settings to make it work.

Want to know how to get past that connect to iTunes logo?

Here’s What To Do

I’ll start assuming you’ve got a factory standard iPhone and iTunes installed on your PC or Mac and you’re ready for a little adventure. I should mention that I’m using a Mac and haven’t done this on a PC. Generally I think the steps should be the same, except you may have an easier time stopping iTunes from interrupting but you may have to run the BlackRa1n application in compatibility mode for Windows XP, if you use that fancy Windows Vista or Windows 7.

Step 1: Sync your iPhone with iTunes

Yep, just as usual, plug your phone in, let iTunes sync any changes and make a backup of the device (You’ll need this later)

While this is going on, you might want to take a moment to download BlackRa1n from http://www.blackra1n.com/ – Just click the logo of your operating system on the homepage. The software is free (Thank you Geohot!), but you’ll want to make a donation using that donate button once you’ve tried it out.

Step 2: Restore the iPhone to factory default settings.

Now you’ve got a backup of your iPhone and a copy of the BlackRa1n app you need, It’s time to restore your iPhone back to factory defaults. It’s just like formatting your iPhone and reinstalling the basic operating software. Technically, you don’t have to do this, but you’re less likely to run into any problems without any third party software on the iPhone. You’ll also become familiar with the Restore button in iTunes, which is what you need to press if it all goes horribly wrong.

Once the restore is done, I got a message that the carrier data needs to be updated, so I went ahead and installed that. Next up iTunes wanted to restore all the data from the backup we just made – How thoughful – but this will have to wait for a minute.

Step 3: Run BlackRa1n

Quit iTunes with your iPhone still connected and run the BlackRa1n application (remember to run in XP compatibility mode if you’re using windows). you’ll see the iPhone display show the Geohot loading screen and, after a little while it will reboot.

Other folks say that the iPhone should now be Jailbroken and life is great. Unfortunately, in my experience, the ‘Connect to iTunes’ logo popped up and I couldn’t get the phone to respond.

Getting Past the ‘Connect to iTunes’ logo screen

Okay this is the most technical part – every time yourJailbroken  iPhone restarts, it will restart in this ‘recovery mode’ and think that it is broken. The solution? Just run BlackRa1n again. Yup, just like before. Ignore iTunes telling you that the phone needs to be restored to factory defaults for a minute and run blackra1n again. This time around, black rain will get you to the springboard (The usual iPhone menu of apps etc). Now you’ve got yourself a jailbroken iPhone and, if you look around your menu, you should find a BlackRa1n app somewhere – on the second page of apps if you’re following this guide precisely – run this app and you can install Cydia, Rock and the Unlock application BlackSn0w.

Now if you reconnect to iTunes, you can go ahead and restore your iPhone from your backup – this will put all your music, movies and apps back on for you.

Troubleshooting

A lot of folks noticed they had problems reconnecting to wifi after going through his process (iPhones don’t remember wifi settings so well after a restore from a backup even if they are not jailbroken in my experience). The answer is to reset your network settings on your iPhone (I’ll assume you know that’s located in Settings > General > Reset > Reset Networks Settings), you’ll need to re-enter your network credentials for all your old wifi networks but also you’ll have to reboot the iPhone to reset this data.

Every time you reboot the iPhone, or if it runs out of battery, you will need to run BackRa1n again to get past the ‘Connect to iTunes’ logo.

Luckily, now that you’ve restored everything from your backup, your music, apps etc. are unaffected and will continue to work normally after you re-run BlackRa1n. The iPhone just thinks it’s in recovery mode every time it starts up and needs to be poked back into normal operation.

This all worked for me, but I already got sick of running BlackRa1n over and over, so I’ve restored my iPhone back to factory settings and I’m gonna wait to see if a non-tethered solution becomes available. I don’t really care what carrier I’m on, so I didn’t try out BlackSn0w, but I hear it’s very good.

Please do let me know if this guide has been helpful to you.