Troubleshoot Sync Services

1. Calendar Events are duplicated in Entourage, iCal and Outlook:

• Office 2008 and Mac OX 10.5.x had know issues with synchronization. There are problems with synchronization that are related to the Time Zone. If your exchange server is in a different time zone than you are, you receive Meeting Requests where the time zone is specified, you specifically pick a time zone for a Meeting Request and then that Meeting Request is updated…..
• The above and other problems are a result of problems with Apple’s Sync Services related to inconsistencies in the format of messages, calendar events, contact information, etc.

Users have reported problems with lost data using Sync Services. There are numerous documents, web pages, blogs, etc. that detail various steps to troubleshoot and attempt to correct this problem without taking the drastic measure of clearing out the contents of the SyncServices folder. However, in my case I have a Mac Book Pro which I purchased prior to Leopard. I updated to Leopard as soon as it was available and I updated Office 2004 to Office 2008 the day it hit the Apple Stores.

I checked the size of my SyncServices folder and found that it was greater than 6GB. Just about every piece of information I read warns you to stay away from the SyncServices folder in Mac OS X 10.4.x or 10.5.x. Removing or modifying in it – or in its subfolders – may cause unexpected issues. This folder is located in your ~/Library/Application Support/SyncServices. Deleting or modifying things in the SyncServices folder may cause unexpected results such as:

• Duplicate contacts in Address Book or appointments in iCal
• Data loss in Address Book or iCal. Important: This is very important – Any data lost or duplicate data could propagate to other devices and computers via iSync and .Mac sync. This means data could be lost on other computers.

There is a sample application you can download for free from the Apple Developer site. It is not so much as the sample application that you want to download but it is the program that comes with the sample program and code – Syncrospector. Syncrospecter is a Leopard program that is part of XCode 3. This application from Apple can help you query the state of your sync services and eventually trigger a slow sync, reset, etc. There is a tutorial for Syncrospector located at:

http://developer.apple.com/documentation/AppleApplications/Conceptual/SyncServicesTutorial/Articles/ViewingSyncResults.html

I used a more drastic approach. For the past few months I’ve been having nothing but problems. If I check the number of my non-recurring meeting requests in Outlook 2003 or 2007 I will see hundreds, associates at work will have meeting requests from me go missing, time zone problems – events will be in EDT on my calendar and the majority of the people I work with are in CDT but calendar events initiated from me will be in EDT on their calendars. I stopped syncing iCal and Entourage a month ago and I now use the tried and true method of dragging an Entourage Calendar event to my desktop and then importing it into iCal. If the meeting request is a recurring event at least iCal will import it as such. However, on the Exchange Server side I should have 30 or so recurring calendar events and instead at least count I had 366 non-recurring calendar events. Somewhere along the way Entourage or Outlook was generating a non-recurring meeting request (calendar event) for every recurring instance instead of creating recurring calendar entries.

I determined that I had to fix this and I had to take drastic measures to do so. In order to completely remove the SyncServices folder you have to shutdown and turn off all Sync Services. In Entourage you need to uncheck the Sync Services in the Preferences Sync Services tab, turn off Apple’s Sync in the System Preferences tab, do the same for Apple’s Address Book and iCal. Turn off every Sync Service you have enabled on your Apple computer. Then use the Activity Monitor or ps -ax|more in Terminal and kill every sync related process you see.

You should also backup any data first, export your Address Book entries, backup your Microsoft Office Identities, etc. Quit all of the above applications. After you remove the SyncServices folder you need to be aware that all of you data on .Mac will be lost and you will be syncing services for the first time.

If you choose to remove the SyncServices folder you need to open a Terminal session and do the following:

sudo killall SyncServer
rm -rf ~/Library/Application\ Support/SyncServices

This stops the Sync Server process then the second line deletes all of the Sync Service directory and subdirectory entries. Next you should run Disk Utility and Repair Permissions. This will ensure that you are starting out clean with all permissions set to how they are supposed to be. Before restarting Sync Services you should check the permissions on the SyncServices directory. In my case I found that the permission list only granted the owner read, write and execute. I updated the folder permission with the following command in a terminal session:

cd ~/Library/Application\ Support
chmod -R 755 SyncServices

You can now open the .Mac System Preferences pane and restart the Sync process. You can open Entourage and enable the SyncServices as well. You will most likely be presented with some prompts asking if you want to replace, merge or delete the sync data in your Apple Address Book and iCal with the Entourage data. In my case I lost all of my Entourage contacts but I have my Apple Address Book entries. I elected to wipe out anything on .Mac and replace it with my Mac’s data to ensure I started over clean. I also choose not to Synchronize my iCal and Address Book in Entourage. I have had so many problems that at some point I will replace my Entourage contacts with my Apple contacts – when Entourage prompts to replace, merge, delete – I will select the appropriate option to force my Apple Address Book entries into Entourage. I have several exports of my Apple Address Book just in case I need to re-import them in the future.

I turned off Time Zone support in iCal because I have read so many articles that state the cause of many sync services conflicts is the result of Microsoft and Apple using different formats for calendar events resulting in Time Zone data differences in the string data. I’m hoping to avoid having to trash my SyncServices folder again and I’ll wait and see if this problem is fixed.

I’ve had very good success with syncing the Entourage Contacts with my Apple’s Address Book but there are some gotchas there too. Some of the format issues are the number of children entries for a contact, the user of multiple email addresses, etc. Apple added a Look for Duplicates Menu Option that helps you to eliminate the duplicate entries.