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Troubleshoot Sync Services & Spotlight

Troubleshoot Sync Services FAQs

  1. Spotlight does not seem to be indexing my Entourage messages
  2. Reset sync services
  3. Force a rebuild with Spotlight
  4. How to re-index folders or volumes
  5. Preference Pane not showing Sync options
  6. All contacts get deleted using Sync-Services
  7. Sync Services crash syncing to iCal
  8. Continuing problems with data corruption
  9. Options for Sync-Replace, Merge
  10. Problems with duplicates
  11. Use Syncrospector to troubleshoot


Some users have reported problems with lost data using Sync Services. These "glitches" are a result of problems in Apple's Sync Services. They're still working at it. Keep regular backups!!!

Read Alerts Carefully!! You could end up erasing data!

On Apple Developer connection, you can download (for free) StickyExample. Along with the sample application comes a VERY HANDY little application called Syncrospector.

In Leopard, Syncrospector is now part of XCode 3. (part of Developer Tools)

This application made by Apple can help you query the state of your sync services and eventually trigger a slow sync, reset, etc... Give it a try.

Tutorial for Synchrospector


Problems with Duplicates If you have the new sync services 11.2.3 update installed, you can use the "Look for duplicate entries" in Apple's Address Book to clean up duplicate contacts.

  1. Sync to push the Entourage duplicates through to Address Book.
  2. In Address Book select "Look for duplicate entries"
  3. Delete entries.
  4. Sync will delete the duplicates in Entourage

Note: Having a middle name in an Address Book contact will cause the contact to be duplicated when it is synced to Entourage. This is supposed to be fixed in Entourage 2008.

UnDupe...For Palm users. Delete duplicates from the Date Book, Address Book, Memo Pad, and To Do List (or Franklin Task List if you are using Franklin-Covey software) separately.

Duplicates in Palm: According to a source at Palm, the reason for the duplicates may be in how the conduits are set. See the Palm Knowledge Library article "Synchronize with multiple handhelds or with multiple desktop computers" can give some insight. Check the section under the heading "One handheld device, two Macs or PCs (or a combination thereof)".

Scripts to delete duplicates

See Continuing problems with data corruption below for resetting your primary source.

Troubleshoot Sync Services FAQs

1) Spotlight does not seem to be indexing my Entourage messages.

Make sure that machine is running on 10.4.3 or newer. There were changes in 10.4.3 that were necessary in order for Entourage to support synching events with iCal, so anything prior to 10.4.3 won't show the preferences pane.

Check to see if there are any files at this directory:


That's where Entourage places files for indexing. More info

Is the Entourage Database Daemon (Office Notifications) turned on? Spotlight will index any cache files the Entourage daemon has created even if the daemon is not launched, but no new cache files will be created until the daemon is launched again. If the Microsoft Sync daemon never launches, there's no way for Entourage to sync data with Sync Services. The preferences in Entourage for Sync Services basically control 1) if this daemon app is launched and 2) where it should sync data to-from. Info on daemon

Is the Sync Services preference disabled in Entourage? If you look at Activity Monitor, is there an app called "Microsoft Sync" running (or runs when you modify something in the Entourage calendar in iCal)?

Spotlight files: .mdimporter

Office 2004: Installs two files: Microsoft Office.mdimporter and Microsoft Entourage.mdimporter

Check for the Microsoft Entourage.mdimporter in these locations: root Library/Spotlight or ~/Library/Spotlight. Mdimport should be able to live in either location--try moving it and seeing if mdimport succeeds. The Microsoft Office.mdimporter should reside in the root Library/Spotlight folder.

Office 2008: Install two files: Microsoft Office.mdimporter in the root Library/Spotlight folder and the Microsoft Entourage.mdimporter in the package: "Microsoft Entourage.app/Contents/Library/Spotlight" bundle

If your. mdimport file(s) are missing, you should use "Remove Office" and re-install to be sure all bits are installed correctly, but if you still do not have this file after doing a clean install, then you can download the files here. Place the files in this folder: root Library/Spotlight/

Files with dates in the future can cause Spotlight to choke. When Spotlight finds these files, it chokes and doesn't know what to do, so it does nothing. I used touch to change the last modified date of the file. you can do it like this.

  1. Find the file in Finder by sorting by date last modified.
  2. Get to the file's enclosing folder in terminal
  3. Type: touch -t (a day before today in this format) YYYYMMDDHHMM "The name of the file"
  4. Rinse and repeat

Do you have Mail Messages. Contacts, Events & To Do Items selected in Spotlight System Preferences? These options do not apply to just Apple's applications.

Entourage items are grouped this way:

  • Entourage Mail items are listed under "Mail Messages" group.
  • Entourage Events & Task items are listed under "Events and To Do Items" group.
  • Entourage Contacts are listed under the "Contacts" group.
  • Entourage Notes are listed under the "Documents" group

If you are using a pre-10.4.3 OS, all Entourage item results will be displayed under the "Other" grouping.

Some users reported they had to restart their Mac to kick things off.

Another user reported...I couldn't get Spotlight to index my mail and I had all the pieces in the right spots. The only thing I didn't have on was "Include Entourage item in search results" checked in the Entourage Preferences: General Preferences> Spotlight. Once I did that everything now works and my mail was indexed.

2) How do I reset sync services and start fresh? (Warning this erases data!!!)

  1. Turn OFF all sync services in Entourage preferences and in your other applications and phones that have sync enabled!!!
  2. Quit ALL Office applications (including Daemon - How to quit daemon)
    1. Note in Entourage 2008, you must quit Office Reminders in addition to quitting the daemon. Previously quitting the daemon quit Notifications/Reminders.
      More info: Quit all Microsoft applications
  3. Quit Safari, Address Book & iCal and all applications synching through .Mac (Transmit, Interarchy, Yojimbo...)
    1. Easy way to quit all Microsoft applications and all other applications: Log out of your User under the Apple in the Menu bar. When you log in, hold down the Shift key to disable all startup items including the hidden ones.
  4. Use Activity Monitor to quit Sync Services
    1. type sync in the search box to locate sync services
  5. Delete the contents of ~/Library/Application Support/SyncServices/
    1. You can also kill Sync Services via the Terminal and delete contents. The first line quits the SyncServer, the second line deletes the SyncService database content to reset it.
      killall SyncServer
      rm -rf ~/Library/Application\ Support/SyncServices/*
  6. Optionally: if you want to replace all data in the system Address book and iCal with Entourage data, delete all iCal & Address Book Data Files in your User's Library folder.
    1. Tiger Users:
      1. Application Support/iCal/
      2. Application Support/AddressBook/
      3. Caches/com.apple.iCal/
      4. Caches/com.apple.AddressBook/
    2. Leopard & Snow Leopard Users:
      1. Calendars/Calendar Cache
      2. Application Support/AddressBook/
      3. Caches/com.apple.iCal/
      4. Caches/com.apple.AddressBook/
    3. See Apple article: TS2481 for additonal info.

      Sync Services: Advanced troubleshooting for contact and calendar syncing
  7. Select Entourage as your Primary Source.
    1. Working off a copy of Entourage, Export your Contacts and Calendar Events as Entourage archive (.rge) file. Select to Delete after Exporting.
    2. Import the file back into Entourage. (this can help with corrupted data)
    3. Remove Duplicates (see this page for scripts that can help remove dupes)
    4. After you are satisified that the data is good, export again as Entourage archive (.rge) file for backup. (In case something goes wrong, you can easily start over and import your file)
  8. Turn ON Sync Services in Entourage preferences.
  9. Restart all applications that sync (Address Book, iCal, Safari, etc.... ). I suggest that you turn on one item at a time and verify that the sync worked as expected. Select in Entourage to have Entourage overwrite the iCal or Address Book items.
  10. Open the .Mac System preferences. Before you turn on MobileMe Sync, select "Replace Information on MobileMe" or the old data will sync back to your newly cleaned up data.
  11. More Info:
    1. Corentin Cras-Méneur, Microsoft Mac MVP's blog for more info on using the Syncrospector.
    2. I suggest that make regular backups of your contacts and events as .rge files. This way if there are problems with sync deleting data or creating duplicates, you can replace the missing data.
    3. Tip: duplicate info has the category "none" assigned. If you give every item a category even if it's a generic catgory like "current", you can sort by category "none" and delete the dupes quickly and easily. More info
    4. Articles on backing up Entourage data

Additonal Links:

Mac OS X 10.5: Resetting the SyncServices folder

If you are attempting to troubleshoot an issue that involves Sync Services in Mac OS X 10.4.x, see this article.

3) How can you force a rebuild with Spotlight?

Click on the Rebuild button. New to Entourage 2008

You can force Spotlight to import the Entourage Cache files by running the following command line tool in Terminal.app:

You manually trigger Spotlight indexing in the Terminal:

mdimport ~/Library/Caches/Metadata/Microsoft/Entourage/2004

You can even force it:

mdimport -f ~/Library/Caches/Metadata/Microsoft/Entourage/2004

The following blog post demonstrates this in action for a iPod music files: http://face.centosprime.com/macosxw/?p=192

4) Spotlight: How to re-index folders or volumes

  1. From the Apple menu, choose System Preferences.
  2. Click Spotlight.
  3. Click the Privacy tab.
  4. Drag a folder or even an entire volume (your hard drive) to the list.
  5. Remove the item or volume you just added.

Spotlight will re-index the contents of the item you initially dragged to the list.

5) Is there a reason why the sync preference item is not showing up in the Entourage preference pane?

Make sure that machine is running on 10.4.3 or newer. There were changes in 10.4.3 that were necessary in order for Entourage to support synching events with iCal, so anything prior to 10.4.3 won't show the preferences pane.

Also, insure there's a file called "Microsoft Sync Services" in the Office folder.

6) All contacts get deleted using Sync-Services

Often this is user error when an incorrect choice is made to sync. Entourage could be syncing with the Apple Address Book and depending on your settings if it's empty it will erase all your addresses.There are still glitches in Sync Services not in Entourage nor Microsoft's Sync Services for Entourage feature. So, logically, if you were going to get mad at someone, it should more rightly be Apple. See this Apple KB for more help.

Anytime you are using a new feature that can add/erase data it's always a good idea to work with backups until you are familiar with process.

A less drastic alternative would be to use Paul Berkowitz's Sync Entourage-Address Book and Sync Entourage-iCal scripts, rather than Sync Services. You can find the scripts here.

Make regular backups of your contacts file.

7) Sync Services crash syncing to iCal

  1. The SyncService database could be corrupted
  2. Events without names are problematic for syncs

Syncrospector made by Apple can help you query the state of your sync services and eventually trigger a slow sync, reset, etc... Give it a try,

Alternatively, you can try a more drastic approach.

I've had similar problems in the past and managed to correct them by completely resetting sync services, but that's a tedious process and it's not risk-free.

Events without names are problematic for syncs: One user reports, I did go through all the resets several times but to no avail. After giving up for several hours I remembered seeing in the log or on the console about "eventname before date" or something to that effect. I went through my Entourage Events and found an event with no name. I deleted this blank event and the sync took off and everything came over.

Another user reports: I looked for blank events and could not find any. Do you have any other recommendations on how to troubleshoot this crash? I know it has something to do with my particular calendar data, because if I create a second calendar in entourage and tell it to use that for syncing, it works just fine. At this time, the only adivce for this situation is to either start over with a new calendar or manually look for the corrupt data.

8) Continuing problems with data corruption

What we know:

1) Sync Services under Leopard and Entourage 2008 has been troublesome even without MobileMe involved.

2) Regardless what you call the process, the sync involves a database called the "Truth" If this database has corrupted data then it will keep repopulating the duplicates and/or other problems over and over.

Basics of how Sync Services Works

You can reset the Truth and create a clean primary source to be used. This has solved the problem for some users. You might even consider only turning on Sync Services to sync then turn it off again until the problems are ironed out. Obviously this is a very complicated process or we would have seen a fix by now. Backup before syncing in case of problems.

How to reset Sync Services