Advanced troubleshooting for Sync Services on Windows with Microsoft Outlook 2003 or 2007

By default, your Outlook data is stored in Personal Folders format (PST) unless you are using an Exchange Server to access your data. If you are using Outlook with an Exchange Server, your data may be stored in an OST file if you have Cached Exchange Mode turned on.  An iPhone syncing via iTunes will sync with the default PST or OST file. MobileMe will only sync with a PST file.  

Note: You may be able to sync your iPhone directly with your Exchange server. For more information on syncing directly with an Exchange server, talk to your Exchange Administrator. There are resources for Exchange Administrators including the iPhone Enterprise Deployment guide on www.apple.com/support/iphone/enterprise/ .

Microsoft provides steps for backing up the data in your PST file used by Outlook in this article.

For information about backing up the data in your OST file, please see your Exchange Administrator. Your OST file should be on the server and backed up when the server is backed up.

Before troubleshooting, it is recommend you make a copy of your iPhone or iPod touch backup in a safe location. For more information about where to find the backup and what information it contains see this article.

It is recommended that your use the latest version to your software:

• For information on using Windows Update to keep your computer up to date see this this Microsoft article.
• You can use Software Update to keep your Apple software used during syncing up to date. For more information see this article.
• For information about updating your iPhone or iPod touch software see this article.

If you followed the steps in HT1692 or TS1681 and were able to sync with Outlook after creating a new Windows user on your computer, these steps may allow you to sync in your original user account. Important: Attempt to sync after completing each step.

1. Make sure all synced fields contain valid information. For example, events without a subject or with other incomplete information may not sync.
   • To check for events with no subject in Microsoft Windows Outlook 2007:
     • Choose View > Current View > By Category.
     • Click the Subject header to sort by subject.
     • Look for events with no subject.
   • To check for events with no subject in Microsoft Windows Outlook 2003:
     • Choose View > Arrange By > Current View > By Category.
     • Click the Subject header to sort by subject.
     • Look for events with no subject.
   • To check for an incomplete Reminder, you will need to search the events individually. A Reminder should include what time to be reminded; for example, 15 minutes before an event.
2. Verify that you have an Outlook profile set as the default. If you have never set a default profile, you will not be able to sync. As long as a default profile is specified, you can still have Outlook set to prompt for which profile to use when opening Outlook. This Microsoft article gives additional information on switching between profiles and setting a profile as your default profile.
3. Verify that you are using a Unicode PST file; for more information see this article.
4. Rename the SyncServices folder. 
   • Disconnect any iPod or iPhone devices.
   • Turn off Syncing in MobileMe Control Panel.
   • Restart the computer.
   • To rename the SyncServices folder: 
     • For Windows XP: SyncServices is stored in a hidden folder named Application Data. You will need to go to Tools > Folder Options and then click the View tab and select "Show Hidden Files and Folders." The folder will then be visible in: C:\Documents and Settings\[username]\Application Data\Apple Computer\
     • Windows Vista - SyncServices is stored in a hidden folder named AppData. You will need to go to Organize > Folder and Search Options and then click the View tab and select "Show Hidden Files and Folders."  The folder will then be visible in: C:\Users\[username]\AppData\Roaming\Apple Computer\
   • Enable syncing for MobileMe or connect an iPhone or iPod.
5. Make sure your security software is up to date and run a security check or scan of your system. Please check with your antivirus or security software maker for steps.  
6. Check your Firewall and Security Software setting.
   • If you are using Norton Personal Firewall or Norton Internet Security, please see this article.
   • If you are using the Windows Firewall, see this article for Windows XP, or this article for Windows Vista.
   • You can use iTunes Diagnostics to check for Firewall related issues as described in this article.
   • Some Security Software may block the iTunes applications from communicating with Outlook or your Outlook data. Please make sure the applications listed in this article are allowed by your security software.
7. Check your PST file for issues with the Inbox Repair Tool (scanpst.exe). Microsoft includes the Inbox Repair Tool with Microsoft Office for diagnosing and repairing some PST related issues. For more information, see this Microsoft Help and Support article. For issues with data contained in an OST file, please see your Exchange Administrator about the OST Integrity Check Tool. This Microsoft Office article has more information on both the Inbox Repair Tool and the OST Integrity Check Tool.
8. If your PST file is larger than 2 GB, you may have issues opening Outlook or syncing with Outlook. This Microsoft Help and Support article has additional information on resolving issues with large PST and OST Files with the Oversized PST and OST Crop Tool.
9. The tools for checking your PST or OST file may not resolve all data-related issues. To assist with isolating the issue to possibly being the data in your OST or PST file, use the following steps:
   • Create a new PST file in Outlook.
   • Set the new PST file as the default. This Microsoft Help article discusses setting and changing which profile is the default profile.
   • Restart your computer.
   • Attempt to sync with the new PST file.
10. If you are able to sync with the new PST file, please follow the steps in this Microsoft Help and Support article to import your data to a new PST file. If the issue returns after importing to the new PST file, the issue is with some of your data. To resolve data issues, the following steps may be helpful.
    • Back up your PST file. For more information see this Microsoft Help and Support article.
    • For Calendar content:
      • In iTunes, select the option "Do not sync events older than 30 days."
        
        • Select the iPhone or iPod touch in the left-hand column in iTunes.
        • Click the Info tab.
        • Scroll down to Calendars and select the option.
      • If the sync is successful, the issue is with an event older than 30 days.
      • Try reducing the number of days to see if the issue is resolved. If you reduce the time frame to 1 day and the issue persists, you know the issue is with an event in the future.
    • For Contacts:
      • Create a group of contacts within Outlook.
      • Open iTunes.
      • Select the iPhone or iPod touch on the left-hand side of iTunes
      • Click the Info tab.
      • Choose "Sync with Selected group."
      • Click the box next to the group you created in Outlook.
      • Add a few contacts at a time to the group and then sync.
      • If syncing is successful, continue adding contacts until syncing no longer completes.
      • Remove the contacts you added most recently and add them back individually until you have isolated the contact that is causing the issue.

If after following the steps in HT1692 or TS1681, you were unable to sync in your existing Windows user, or in the new user you created, these steps may resolve your syncing issue. Important: Attempt to sync after completing each step.

1. Restart your computer by shutting it down completely, leaving it powered off for 30 seconds, and then powering it back on. If you are using a USB hub, unplug it from any power source while the computer is powered off, and plug it back in once your computer has started up.
2. Make sure the date and time are correct on your computer and iPhone or iPod touch.
   
   • To adjust the date and time on your Windows computer, right-click the current date and time in the task bar and choose Adjust Date/Time.
   • To adjust the date and time on your iPod touch, be sure it is unplugged and then go to Settings > General > Date/Time > Set Date & Time.
   • On some computers you may need to update your date and time in the BIOS (for example, if your time resets each time you startup). Please contact your computer or motherboard manufacturer for assistance.
3. Make sure your security software is up to date and run a security check or scan of your system. In addition to updating any virus definitions or firewall rules, update the security applications as well— check with your antivirus or security software maker for steps if you are unsure how to do this.
4. Make sure your firewall allows all related Apple software.
   • If you are using Norton Personal Firewall or Norton Internet Security, please see this article.
   • If you are using Windows Firewall see this article for Windows XP, or this article for Windows Vista.
   • You can use iTunes Diagnostics to check for Firewall-related issues as described in this article.
   • Some Security Software may block the iTunes applications from communicating with Outlook or your Outlook data. Please make sure the applications listed in this article are allowed by your security software.
5. Use the "msconfig utility" to isolate programs loading on startup that could be interfering. See this article for steps if you are using Windows XP, or this article for Windows Vista.
6. Verify the issue is not with the data on the iPhone or iPod touch.  
   • Try replacing the data on the iPhone. In iTunes, scroll down to the Advanced section in the Info tab. Choose the option to replace the data on the iPhone during the next sync.
   • Rarely, the data on the iPhone may not be replaced. If the issue persists, try testing on a different computer and with a test user account on that computer. If using a computer with Outlook, be sure to open Outlook at least once prior to syncing. If you are not able to sync with the iPhone on a different computer, the data on the iPhone will need to be restored. This article contains information about restoring your iPhone.
   • If you do not have access to a different computer, copy the iPhone backup to a different location on your computer. For information on where the iPhone backup is stored see this article. Once you have copied your iPhone backup, restore the iPhone and choose to setup the iPhone as new when prompted. After this, test syncing. If you are unable to sync after the restore, you can restore the data from the backup to the iPhone. For information on backing up, restoring, and restoring from backup please see this article.
7. Reinstall Outlook with default installation options. This includes installing the program in Program Files on the same drive that Windows is starting up from.  
   
   • If you use Microsoft Outlook 2003, follow steps in this Microsoft article to reinstall.
   • If you use Microsoft Outlook 2007, follow steps in this Microsoft article.
   • Install all available updates and Service Packs for your version of Outlook after reinstalling.