Calendar – Outlook does not sync with iPhone / iTunes

When you uninstalled iTunes, did you uninstall iTunes and all of its components as described here:http://support.apple.com/kb/HT1923? If you don't follow this guide it will not work.

Generally I find the corrupt file is from a bad appointment. Do you recall setting an appointment about the time this started happening. Have you tried to run the scanpst file on your Outlook file. Scanpst.exe resides in the main Microsoft Office folder. You should be able to do a search of your computer and locate it. Then you also need to know where your Outlook data file is. It ends in .pst. After running the scanpst file, it should repair problems that you might have. Also, make sure you have applied all of the updates to your Outlook. I have successfully synced with Outlook 2003, 2007 and now with 2010. If the scanpst does not help, then try putting the calendar into detail view and see if you can see something wrong with an appointment. There used to be a problem with recurring appointments with no end date, but I believe that was corrected in a newer iOS update. Some thought it had something to do with the older version of Outlook.

The last thing you can do is to export your outlook.pst file and save it on the desktop. Then go into Outlook and create the new data file by opening the exported file. That might correct it if nothing else does.

Generally it tends to be a recurring appointment with no end date. I upgraded from 2007 to 2010 sometime back and did not have a problem. Obviously from your test there is a bad appointment, since importing the old data seems to replicate your problem. Maybe you could try creating a new calendar, put an appointment in it and see if that calendar syncs. In iTunes, just select that single calendar to sync and see if that works. If it does, then try moving a month of appointments at a time and see where it stops syncing. That could help identify it. You don't mention if you tried the scanpst.exe fix, did you? How many appointments are you talking about having to re-enter if you cannot get the sync to work? If it isn't too many, it might be worth just deleting the calendar and starting over.

I have also used Outlook for a long time. I also teach Office classes at a community college, one of the reasons I like to understand when people have problems. It is especially interesting to me since I have an iPhone and many of my students do as well, and I like to be able to handle any problems I can. I have found that many times moving an Outlook data file from an older to newer format can cause issues. I have tried a number of different things in the past to try and get around problems. I have archived an Outook file, then deleted the current Outlook file and imported the archive. Sometimes things that drastic will work. Up to you how far you want to go with it, but you can try to export your entire Outlook file, close Outlook, delete your Outlook.pst file and then open Outlook and import the backup you made. However, if you have a lot of calendar entries to replace, you might not want to try that. The next thing is how do you have your auto-archive set up? How much of your calendar is not in the archinve file? You should only really have a little more than 30 days of data in your calendar anyway, 90 at the most. If there are not that many entries there, you can always try and delete them and re-enter.

This fixed it for me. I located and deleted recently changed or added recurring appointments and that fixed the problem.

This was my resolution - no data lost:

1. verified iTunes had a recent backup of my iPhone 4s. (in iTunes, under “Devices” right-clicked on iPhone and then clicked “Backup”.
2. in iTunes, under “Devices” right-clicked on iPhone and then clicked “Restore from Backup”.
3. As normal, when there was a conflict between contacts, chose which device I wanted to use (Outlook or iPhone).
4. Performed regular sync (since when prompted I elected to wait in step above).

Only problem was one recurring, all-day event that duplicated itself. Deleted duplicate event and all is fine. Two-way communication restored.

Specifics: iPhone 4s, Windows XP, Outlook 2003, only problem was syncing iPhone calendar to Outlook. Notes, contacts, etc, worked fine.

For me disabling "exchange cache" in the Outlook 2003 settings resolved the problem..

Fantastic thread! Thanks. My iphone 4 and my iPod had both stoppped syncing with OUtlook 2010 Calendar and I thought I'd tried everything. The recurring appointmment without end date was the solution and as soon as I corrected that everything behaved properly.

Well done and thanks again.

Thank you!! Thank You!! Thank You!!! This thread solved my long standing calendar sync problem. I deleted all my non ending recurring calendar entries such as my monthly mortgage payment and credit card payment due date entries on both my desktop calendar and my iphone calendar and it synced right away. No data lost except I don't have my recurring items. I guess I will just have to remember to pay my mortgage every month. Absolutely a great thread. Thank you.