The Burton Tech Journal

Duplicate Items in Exchange with at least one Entourage Client

by on Sep.15, 2008, under Microsoft Entourage 2008, Microsoft Exchange, Microsoft Office

A client of mine recently contacted me with a number of Exchange related problems.  Various company Executives were seeing duplicate and vanishing appointments in their Entourage Calendar.  Most of the company Execs were on Macs using Entourage 2008, while their assistants were using Outlook 2003/2007 on Windows based PC’s will full delegation rights.

After examining the Exchange entries, it appears the duplicates were being created solely by the Entourage clients.  Further examination of the Mac clients revealed that they also had the Sync Services Enabled for Entourage.

Entourage Preferences - Sync Services

By disabling the Sync Services for Entourage, it eliminated duplications from the corrupted truth database.  Unfortunately, some of the Execs wanted Entourage data to continue to sync with their .Mac accounts, despite the same information being available from any web browser via OWA.   This required fixing the somewhat buggy Sync Service.

The Sync Service works as an intermediate between your various applications/devices and the data they contain.  When an application like Entourage syncs with the Sync Service, the data is copied from Entourage to the truth database.  At that point, other applications like iCal further synchronize the data with the truth database.

iCal <–> Truth DB <–> Entourage <–> Exchange

For an excellent article on sync’ing, check out the Entourage Help Blog and “Why does syncing play Gossip with my contacts?“.

To fix the issues my clients were experiencing, I had to purge the corrupt truth database and re-sync using Entourage as the master database.  If you want to do something similar, follow these steps:

  1. Back up all iCal, Address Book, and Entourage Data.  If you fail to do this and make a mistake, you will lose data.
  2. Turn OFF the Sync Services for Entourage in the Entourage Preferences on ALL clients that connect to the Exchange server.
  3. Remove the duplicate items in Entourage using these tools.
  4. Delete duplicate iCal appointments using John Maisey’s iCal Dupe Deleter.
  5. WARNING: The remaining steps will delete data – Make sure you have a valid BACK UP before proceeding.
  6. Quit all Microsoft Office applications except Entourage
  7. In the Entourage menu select “Turn Off Office Reminders”
  8. Quit Entourage
  9. Start the “Activity Monitor”, select “database daemon”, and choose “Quit Process” from the Processes Menu (perform a Normal Quit, not a Force Quit)
  10. Quit iCal, Address Book, Safari, and any other applications that sync with a .Mac account
  11. Use Activity Monitor to quit the Sync Services
  12. Delete the contents of ~/Library/Application Support/SyncServices/
  13. Since Entourage is going to be the primary source of data, delete the iCal and Address Book data files:
    • Delete  ~/Application Support/iCal/*~/Application Support/AddressBook/*
    • Delete  ~/Library/Caches/*
    • Delete  ~/Library/Caches/*
  14. Open the .Mac applet via the System Preferences and Verify .Mac syncing is enabled
  15. Restart all applications that sync with .Mac (ie, iCal, Address Book, Safari, etc)
  16. Turn on the Sync Services in the Entourage Preferences
  17. When prompted with the “Replace, Replace, Merge” dialogue, since we select Entourage to be the primary source of data, make sure to choose “Replace Sync Services items with Entourage items”.

From what I have experienced, synchronizing an Exchange linked Entourage client with a .Mac is frequently problematic and I do not recommend it at the time this article was written.  If you must use this functionality, make sure to always make additions/changes/deletions from one machine and with a single application.  You should then give some time for synchronization to occur before using another machine/app.  As you can imagine, this can be an issue for users with delegates constantly changing Exchange data from another machine!

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