Fix-it: iPhone “Sync Session Could Not Be Started”

by Michael Sheehan on November 17, 2008

in Apple, Cellular, Fix It, Gadgets, General, Hardware, HTD Tech Tip, iPhone, Software

Well this past weekend I ran into a rather confusing problem which I did manage to resolve, however, I’m not sure exactly how I resolved it nor what really caused it. I have some ideas on both the cause and resolution so I will try to work through those here. This all came when I tried to sync my iPhone to iTunes (on my Mac). I plugged it in and it started to sync and I got the rather cryptic error message (image below) saying: “iTunes could not sync <item>to the iPhone ‘<insert iPhone name>’ because a sync session could not be started.” For me, the <item> was my Bookmarks, supposedly, but in the end, it was Contacts as well.

synch_bookmarks_issue

That makes a lot of sense, right? So, first my “environment”

  • iPhone was “supposed” to be syncing contacts through iTunes
  • Plaxo for Mac installed and syncing contacts (supposedly)
  • New version of Plaxo installed recently
  • MobileMe configured but not syncing anything
  • Last.fm recently installed

Some weirdness that was happening:

  • When syncing, I would get the error message about the bookmarks (above)
  • For a time, when I tried to select or unselect my bookmark toggle on the iTunes Info tab (under the iPhone) and click Apply, the toggle wouldn’t stick
  • The same thing would happen when I tried to select the “Sync Address Book Contacts”; the toggle wouldn’t stick
  • Under the address book setting in iTunes, none of the groups that I have set up within my Address Book were showing
  • None of my recently added Contacts in the iPhone had transferred over to my Address Book

Things that did NOT resolve my issue:

  • I tried Resetting the data on my iPhone using the Settings > General > Reset > Reset All Settings –> FAIL
  • Uninstalling Last.fm completely –> FAIL
  • Reconfiguring MobileMe to sync my Contacts and Bookmarks (later unconfigured) –> FAIL
  • Reboot Mac –> FAIL
  • Reboot iPhone –> FAIL
  • Rebuild permissions on Mac –> FAIL

What I DID do to resolve the issue (note, this worked for me and I’m not going to try to recreate the issue; I just wanted to document some steps that corrected the issue – it could have been a combination of things):

  • Disabled the Plaxo Mac syncing of contact –> that ALONE did not resolve but I wanted to eliminate that as an issue
  • Reset my iSync Sync History:
    isync_preferences
    Simply launch iSync and go to the Preferences for it and click the “Reset Sync History” –> I think this was causing some of the issues, however, it didn’t truly get my iPhone synching as expected until I ran the step below. This may work for some of you.
  • What I think WORKED. Ran a manual reset of my iSync using instructions found here. These are:
    1. In the Finder, choose “Utilities” from the “Go” menu
    2. Open “Terminal”
    3. In the terminal, type in or paste (without quotes): “/System/Library/Frameworks/SyncServices.framework/Versions/A/Resources/resetsync.pl full
    4. Press “Return”
    5. When complete, quit “Terminal”
  • After resetting the Sync, try launching iTunes again and connect your iPhone. When I did that, I suddenly was able to see my Address Book groups and the selection boxes were working. NOTE: I had to restart iTunes a few times to be sure that this took.

I have not yet re-enabled Plaxo. I wanted to be sure that all of my new Contacts that I added to my iPhone were syncing across properly. They finally were. And, my Bookmarks were syncing as expected.

If any of you are having similar issues AND one or all of the tips above worked, please leave a comment so that others can track the solutions to this issue.

Did you find this solution useful? If so:

HTD says: Syncing is a pretty complex thing. When troubleshooting, just start eliminating other 3rd party items first, then go from there.

Print Friendly
  • Clive

    The manual reset (using the terminal command above) worked for me (I don't have Plaxo). Just FYI.

  • Clive

    The manual reset (using the terminal command above) worked for me (I don't have Plaxo). Just FYI.

  • http://tekfreak.blogspot.com/ Duncan

    Thank you HTD!!!.

    Thank you!!! Thank you!!! Thank you!!! Thank you!!! Thank you!!!

    I was going nuts, because I coudn't solve this issue until I found your blog

    It work for me. I had to repeat the resync thing several times from both the isync and terminal. Then I had to restart the itunes several times and finally it showed the calendars. Note that I had the same problem with the contacts -the contact groups woudn't show up- and until the first sync they woudn't be shown

  • http://tekfreak.blogspot.com/ Duncan

    Thank you HTD!!!.

    Thank you!!! Thank you!!! Thank you!!! Thank you!!! Thank you!!!

    I was going nuts, because I coudn't solve this issue until I found your blog

    It work for me. I had to repeat the resync thing several times from both the isync and terminal. Then I had to restart the itunes several times and finally it showed the calendars. Note that I had the same problem with the contacts -the contact groups woudn't show up- and until the first sync they woudn't be shown

  • Alice

    Worked beautifully, thanks so much.

  • Alice

    Worked beautifully, thanks so much.

  • Jason

    It is fitting that on Father's Day, I found your blog and it fixed my month old syncing problem with my first gen iphone. I had been to the apple genius bar twice where we archived and reinstall of os, twice restored my iphone and even tried a new 3G, but to no avail. Once I executed the resetsync perl script (after I got home the second time), things started working again. Thanks for posting.

  • http://yourappletrainer.com/ Chris P.

    Thanks for your post. I believe resetting iSync with the terminal commands was exactly the fix. I just upgraded to Snow Leopard and ran into this same problem. Tried all the same steps you did initially. So once again thank you for posting this!

  • http://www.facebook.com/katanyoo กตัญญู อุบาลี

    Ohhhh!!!! Thank you Very much!!!!!!

  • andrew

    Awesome!! Thank you so much. This problem was driving me nuts. Your solution fixed it. I greatly appreciate it.

  • andrew

    Awesome!! Thank you so much. This problem was driving me nuts. Your solution fixed it. I greatly appreciate it.

  • http://www.cheapshoeshop.com wholesale shoes
  • Enistali

    Thank you sooooooooooo much!!!!!!

  • Clay

    Worked for me like a magic, really thanks!

  • Sheril

    Resetting my sync history by going through Preferences in iTunes worked! Thank you so much!

  • Star

    I’m having the same issue however I’m on PC. Spent 3 hours on the phone with Senior advisor from Apple and we still coudln’t figure out my issue.

  • Guest

    yes, it worked for me.  It’s important a user puts ‘full’ as the argument otherwise things actually get a little worse!

  • Guest

    Thank you!  I have being trying to fix this for a week after turning on and off iCloud!

  • Cindy Wolf

    the reset did not work for me, Terminal returned the following message: “There is no (UpgradedbTries) default for the (com.apple.SyncServer) domain.Defaults have not been changed.” Now what? sigh. I was so hopeful that your solution would work. Apple also has it listed in their trouble-shooting guide for syncing problems.

Previous post:

Next post: