Sync Services still causing problems for some users after SP1

Some customers still see problem with Entourage’s Sync Service after upgrading to SP1. For example, they see frequent crashes in Entourage’s sync service and constantly see conflicts for the same set of contacts and events in the sync alert dialog although they have resolved the conflicts previously.

Solution: Reset sync service in Entourage and the sync service in the OS. Until you clean up your data stored in the truth (a special database that stores sync information on a Mac), you will continuously sync bad data and duplicates over and over.

For this cleanup process, I recommend these steps;

  1. Turn Off Sync Services for all your apps
  2. Clean up duplicates in one source (I suggest Entourage)
  3. Turn On Sync Services
  4. Follow the steps below to reset Sync Services (this will erase data)

Note: Always backup before deleting data!

Cleaning up Duplicates

* I find using the third party applications to delete in Apple applications the quickest easiest option.

Reset sync services and start fresh (Warning this erases data!!!)

  1. Turn OFF all sync services in Entourage preferences
  2. Quit ALL Office applications (including Daemon – How to quit daemon)
  3. Quit Safari, Address Book & iCal and all applications synching through .Mac (Transmit, Yojimbo…)
  4. Use Activity Monitor to quit Sync Services
  5. Delete the contents of ~/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:
    1. Tiger Users:
      1. Application Support/iCal/
      2. Application Support/AddressBook/
      3. Caches/
      4. Caches/
    2. Leopard & Snow Leopard Users:
      1. Calendars/Calendar Cache
      2. Application Support/AddressBook/
      3. Caches/
      4. Caches/
    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. Make a copy of Entourage before starting.
    2. Export your Contacts and Calendar Events as Entourage archive (.rge) file. Select to Delete after Exporting.
    3. Import the file back into Entourage. (this can help with corrupted data)
    4. Remove Duplicates (see this page for scripts that can help remove dupes) or use one of the third party options listed above.
    5. After you are satisfied 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)
    6. Turn ON Sync Services in Entourage preferences.
    7. 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.
    8. 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.

Note: Currently syncing with .Mac has problems. You might not want to sync to .Mac at this time.


There’s a dialog that pops-up in Entourage when you turn on syncing of a calendar or address book that asks something like: “You have enabled Sync Services for a folder, do you want to?

If you have selected Entourage as your primary source, you will want to select

  • 08: Delete information from Macintosh Address Book, iCal and .Mac
  • 04: “Replace Sync Services items with Entourage items”

Entourage 2008 Options:

Entourage 2004 Options:

Replace Entourage items with Sync Services items
Replace Sync Services items with Entourage items
Merge Entourage items with Sync Services items

The “Replace Entourage items” option will delete all items in Entourage and override them with the contents of the Sync Services truth. You’d want to do this if you haven’t used Entourage in a while or you consider your cell phone’s address book the primary “rule” for your contacts.

The “Replace Sync Services” option makes Entourage the short-term rule. All contents within your truth will be deleted and replaced with Entourage items. In this case, all contacts in your Address Book app would be deleted and then replaced with those from the address book selected in Entourage.

The “Merge” option is normally the safest option. Nothing gets deleted. Items in the Sync Services truth go into Entourage and items within Entourage go into the Sync Services truth. Because this can be a bit messy, causing duplication, or unwanted items this is not an option we want to use for this process.

After selecting one of these options, all changes in anything that talks to the ‘truth’ will be synchronized to any application that listens.

Recommended reading: Basics of how Sync Services Works

[Edited July 06, 2009. Added screen shot for Entourage 2008 to show differences with Entourage 2004 preferences for Sync Services.]

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16 comments to Sync Services still causing problems for some users after SP1

  • John

    I’ve done all of the above 4 times now. I still can’t get sync services to put my Entourage calendar items in iCal.
    Which of course means I have an empty calendar on my iPhone….which means I have a worthless phone and will have to switch back to a BB until July 11th.
    Seriously, I can’t think of what the issue is… the sync with Entourage 08 has worked for months.

  • Diane Ross

    Try testing in a new User. Go to System Preferences –> Create a New User in Accounts. Switch to the New User by logging out/in or use Fast User Switching. You will need to drag your Microsoft User Data folder to Shared so you can drag it to the new Documents folder. (it copies so you data is safe… just drag it back from Shared when finished)
    Turn on Sync Services and see if it syncs with iCal in the new User.

  • i’m using Entourage 2004 to connect to an Exchange server. For some reason calendar and task information is not being synchronized between the local information and the server. I can’t see the information if I access Exchange using Web Access, and changes made there don’t show up in Entourage

  • Diane Ross

    This type of question is not related to Entourage 2008 SP1 and is best asked on the Entourage newsgroup.
    How to subscribe to the MSFT newsgroups
    Be sure to include the version of Entourage plus updates, your OS, type of machine, server software and what you have tried. Make a subject with Exchange in the first part so it gets noticed by the Exchange experts.
    See you on the newsgroup!

  • PNM

    I have now tried this fix, four full times. I have set a new user and everything works fine. The Entourage/ICal sync has worked flawlessly until 12.1.0. and OSX 10.5.3. Now contacts work great but nothing else. Had hoped, 12.1.1 would fix the problem. Repeated the steps and >>>Nothing.
    I use my calendar a lot….Project managemnt suff which I love in Entourage. Can’t someone get this problem fixed?

  • Diane Ross

    Since Entourage uses Apple’s Sync Services, the fix is probably going to come from an Apple update. Maybe the MobileMe release will be the trick.

  • John

    Yeah, I’m back. New user trick worked for about a day. Get this though…. I have three options to use with Entourage’s sync services in the calendar section.
    Local Calendar
    Calendar1 – Exchange Server
    Calendar – Exchange Server
    The problem is, I ONLY have CALENDAR1. Same with my contacts, folder is Contacts1. For some reason if I select Calendar1 I get an empty iCal. If I select Calendar, aka no 1, that should be empty…that populates iCal…. ONCE. No updates are synced. ??? What gives. Perhaps it’s something in the way it reads the folder from exchange and if it’s just a slightly different folder name… all bets are off. BUT that should break my Contact sync too…but it doesn’t.

  • Diane Ross

    Let me run this past one of the Exchange folks. I’ll get back.
    I sent you a message off list. Please check for it.

  • Harry Zink

    Of course, the easier solution would be to actually either hire programmers that know what they are doing, or to provide proper QC during the production process.
    Since this fails during the initial planning phases (“planning? What’s that?”), combined with a group of programmers wholly unfamiliar with proper Mac design practices and framework usage, none of this is any surprise.
    Not that it isn’t par for the course for the disappointment that is Entourage 2008.

  • Diane Ross

    From your other similar comment on another post, I can tell that you are not a happy user. As I advised in the other comment, it’s best to send your comments to Microsoft where it might actually do some good.
    Our goal is to help users with what we have.

  • John Harte

    I’ve got the same Calendar1, Contacts1, Drafts1, issue.
    Only in Entourage 08 though, in a hosted virtual desktop I have Outlook 07 pointed out the same account, in that folder list everything is named correctly (Calendar, Contacts, ect).
    I’ve completely removed my exchange account, removed the identies and rebuilt them… STILL calendar1, ect…ect.
    This also effects my iPhone b/c sometimes appointments make it to my iPhone, other times they don’t. I’m guess it depends on what email client I use to add the appointment, Entourage or Outlook 07.

  • Kerry Dawson

    I’ve had trouble with sync services in entourage since the day I bought it. If i just enable one module, in my case calendar being the most important, it works flawlessly and I have worked this way since mid Feb. Enabling more than one module always messes up my calendar. I rarely add notes or change or add contacts but if I do, I turn of calendar in Entourage, delete the Entourage calendar in iCal (of course everything including the main identity is backed up) turn on Addressbook, choose combine and voila now Addressbook is current in iCal, my Palm and my BB. Now I turn off Addressbook, turn on calendar, choose combine and it recreates an Entourage calendar in iCal. Again, its perfect and runs flawlessly I find for ages. Although it is annoying to go through these steps, as I said I rarely change the other modules so I haven’t found it such a big deal. But I do want to work in Entourage due to its power and not the Apple apps. One thing, after doing this, in Missing change your conduit settings for first time desktop overwrites device so the data is clean. Again, it works without problems always.

  • David Garrison

    I’ve had a recurring problem for several months now: The Entourage calendar in iCal will not stay in place. It removes itself after several days.
    I have (in no particular order):
    – deleted .plists
    – Reinstalled OSX – several times
    – Reinstalled Office 2008 – several times
    – deleted Microsoft User Data
    – reset Sync Services – more times than I can count
    Today I began receiving sync alerts that deleting the Entourage calendar would change more than 25% of my calendar. I did not delete the calendar, though. I cancelled the sync. After 5 of these notices, the Entourage calendar disappeared from iCal again.
    I also noticed that Microsoft Sync Services was “not responding” in Activity Monitor. I am convinced the problem is with Microsoft Sync Services, but I don’t know what to do about this.
    It is very important that I have my Entourage calendar in ICal, so I can sync it to my iPod Touch. How do I get this fixed?

  • Diane Ross

    Reinstalling rarely fixes problems like this. The problem is in the .plists and Sync Services. Currently, since Sync Services are such a mess, you might want to consider letting Entourage sync once a day then turn off Sync Services to see if that will help. Manually toggling this option might improve the situation.
    See the steps listed in this FAQ. It involves some of the same options you have tried, but it includes an additional step.
    Have you checked out iPDA? I don’t have any personal experience with it, but it’s worth a look.
    I would also scan the Apple Discussions: iCal since it’s iCal that’s misbehaving.
    Let me know what happens.

  • Ian McShane

    Thanks for this article.
    I think the “Replace, Replace, Merge” part of it is a little out of date now as this screen differs to your description.

  • Thanks for the heads up. I added screenshot for Entourage 2008 to clarify the differences between 04 and 08 Sync Services preference.