I’m getting annoyed with all those problems I encounter since the upgrade to iOS 4 and iTunes 9.2. At first I was very pleased with the new look and features. But now after a couple of weeks more problems show up. They’re not fatal but all those small issues pile up to a Windows-like hurdling. I just want to use my Mac and iPhone to be productive! Every now and then a new error stops me and then I have to google around to find and try another fix. Meanwhile I try to keep my hope that Apple will release an update to iOS 4 and/or iTunes 9.2 soon.

So here is my latest iTunes/iPhone sync problem.

Problem

Yesterday the iPhone backup process got stuck at around 70% (maybe more but doesn’t matter). After about an hour of watching nothing happening I just unplugged the phone. Since then no attempt to sync my iPhone with iTunes has been successful. I always got these messages:

“iTunes could not back up the iPhone “<iPhone name>” because a session could not be started with the iPhone.”

“iTunes could sync information to the iPhone “<iPhone name>” because another sync session was already running.”

I thought the last backup session has been broken and will be discarded the next time I start iTunes. Not luck there. Ok, restarting OS X may help but no change either. Then I came across an article in Apple’s support site. The solution in the knowledge base article sounded reasonable and matched the description of my problem close enough.

Solution

Delete the broken backup. That’s it. How do you do it without opening a terminal?

  1. Open iTunes > Preferences > Devices
  2. Select the broken backup (probably the most recent one)
  3. Click Delete Backup
  4. If this didn’t help try hard resetting your iPhone. (Hold Sleep + Home buttons down until Apple logo appears)

This worked for me to remedy the issue of my iTunes not willing to backup my iPhone 3G any more. During the broken backup all my notes on the iPhone were gone but came back after the successful backup.

After this problem occured for the 2nd time a week later I had to do step 4 before I got the sync working again. The first time deleting the faulty backup did the trick.

Some users also reported a change of the time zone on your computer may help.

My setup is a MacBook Pro 5,1 (15″ unibody, late 2008) with current OS X 10.6.4. The iPhone is a 3G (not 3GS) with iOS 4 (GM).

Please share your experience if this was helpful or not to you.

Update

This is getting a bad habit of iOS 4. From 4.0 to 4.1 beta 3 Apple didn’t acknowledge or fix this problem. I’ve been able to identify and reproduce 2 situations that result in a broken backup:

  1. Unplugging the iPhone while syncing with iTunes. At first this seems obvious but should be handled correctly by the the software. Never caused any trouble before on iPhone OS 2.x and 3.x.
  2. Receiving a call while connected to iTunes. While syncing and when still connected after a successful sync. Both situations lead to a broken backup and happened to me several times yet. Stop calling me when my iPhone rests in its dock! Actually it doesn’t happen every time I get a call but happened twice.

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13 Responses to “How To: Solve iTunes 9.2 and iPhone 3G iOS 4 sync problem”

  1. Matt says:

    Thanks for the great tip. :) I had exactly this problem just now after I force quit iTunes when the backup progress bar was stuck below the “P” of “iPhone”.

    Deleting the backup and restarting iTunes didn’t fix the problem for me. However, rebooting the iPhone did the trick.

    Thanks again!
    Matt

  2. jERRy says:

    Thanks for your feedback. The first time it occured I didn’t need to reboot my iPhone. And last time (yesterday) just rebooting the iPhone didn’t help either. So I had to perform all 4 steps mentioned above.

  3. Steve says:

    I’ve got the same problem. Deleting last backup and hard reset failed to cure. I still get the “iTunes could not back up the iPhone “” because a session could not be started with the iPhone.”

    iTunes 9.2.1
    iphone OS 4.0.1

  4. Andy says:

    I have the same issue. nothing has worked. I have deleted backups, changed time zones and hard reset. Its been 3 weeks since I have been able to sync my iphone. Big bummer here.

  5. Jamie says:

    Have any of you guys tried completely removing itunes 9.2.1 off of your mac os x. Tha could potentially work?

  6. jERRy says:

    No, I haven’t tried downgrading. I’d rather wait for an update if that is the cause. Had this problem again yesterday after a call came in just while syncing. Had to take the call and then the backup was broken again… But I was able to fix it by resetting the phone and deleting the backup. Didn’t even restart my Mac, just iTunes.

  7. Oscar says:

    The hard resetting of my iPhone worked perfectly, at first iTunes said it could not complete the backup because of an error, and then I clicked Sync again and it backed up and synced perfectly!

    This was after the force quitting of iTunes after a of my phone backup froze.

  8. paulo vr says:

    I’m with Oscar – hard resetting finally did the trick. This was getting annoying – I already had to do a full restore (as in, drop ALL my data) to make my 3G perform decently on iOS4. Srsly, Apple is being pretty lazy and terrible these days…

  9. jERRy says:

    Thanks for your feedback. iOS 4.0 is killing productivity on the 3G but 4.1 (currently beta 3) works pretty well so far. Especially the UI responsiveness and overall stability have much improved. So be patient, I hope the final 4.1 will be released soon.

  10. John Torres says:

    The hard reset seems to be working for me. Thx all!

  11. webbi says:

    Thanks for this posting, it worked fine. Deleting the old backups didn’t help at first, but the hard resetting finally helped – my iPhone is synching right now.

    I use iTunes 10 and iOS 4.0 on my 3GS. The bug came up when I plugged my iPhone out while it was synching with my Mac…. Damn, I won’t ever do that again.

  12. Jacopo says:

    I had to force quit iTunes while syncing the iPhone because it had been syncing for 1:30 hours so I assumed it was stucked. I’m kind of scared about hard resetting, though.

  13. jERRy says:

    Nothing to worry about a “hard” reset. It won’t reset any personal data or configuration but force a reboot of your iPhone. btw this also helps calibration of the battery indicator as described in my other post.
    You could compare it to pushing the reset button on a PC if it got stuck.

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