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Using Entourage with Leopard

Office 2004 and Office 2008 are compatible with Leopard.

Most problems reported so far on the Entourage newsgroup are specific to the individual reporting the problem. These seem to be tied to the type of install used. There are three types of install options for Leopard:

  1. Upgrade Mac OS X (the default upgrade method)*
  2. Archive and Install
  3. Erase and Install

* Personal comment: Just because it's the default doesn't mean it's the best option.

Here's what each method does.

Users that use Erase and Install have the fewest problems. Consequently, I recommend using Erase and Install followed by Archive and Install. If you have space to do a complete backup of your Tiger volume, you can use the Migration Assistant to import your data after installing Leopard. This will bring over your network settings. Regardless when doing a major update, you should backup your data first.

Disabling AntiVirus Software when creating your first Time Machine backup: I was doing some research on Time Machine in the Apple Discussions list and found that AV will virus-check everything writing to the Time Machine drive. Since there's no way to exclude a drive in AV10, you have to disable AV. One user reported 20-hour long backup went to 20 minutes! (Update for AV allows you to exclude drive)

Also you should exclude the Microsoft User Data folder or Identity from Time Machine backup on an hourly basis. If you backup your Identity while it is being used, the data coule be corrupted. See Quit all Microsoft applications before backing up

  • Lose some data or
  • have a corrupt backup file.

Options to backup your data:

Spotlight and Time Machine: I also suggest that you exclude Spotlight from indexing your Time Machine volume in the Privacy tab of Spotlight, as well as, the Entourage Identity file in your User's folder. Spotlight actually indexes files created in your User's Library folder rather than your Identity. BTW, Spotlight search in Entourage 2008 is blazing fast! (note it's possible this is now done automatically, but I can't find documentation that it is excluded)

.Mac Syncing: The new .Mac sync is big on syncing everything between different Mac's including preferences. It seems that this preference sync is far from being intelligent (at least it seems like that) but more like a raw dump. The multitude of possible hardware software combinations that are possible seems to be too diverse especially if you are mixing different operating system versions (10.4.x - 10.5 ). I would recommend disabling the "Preference" sync feature on .Mac until applications on all machines are updated.

Reported Problems and Questions using Entourage in Leopard:

1) Office 2004 will not open and/or nothing working as expected (missing document window)

Disable preferences for dot Mac Sync. To test for corrupt preferences, create a new User in System Preferences and test there with .Mac preference sync turned off.

2) Crash if click font color button

Turn off ALL Office programs, including Entourage's Notifications; manually trash Office Font Cache (11), shut down the Mac and re-start.

~/Library/Preferences/Microsoft/Office Font Cache (11)

Note: 11 indicates it's an Entourage v11 file. Entourage v11 is Entourage 2004.

Another user found that running the Apple standalone 10.5.1 updater fixed his problem after clearing the cache failed. Often standalone updaters work when the download file through Software Update fails. See this page for an explaination on the different types of updaters.

3) Problem: Entourage 11.3.6 seems non-responsive (or sluggish) to mouse clicks since updating to Mac OS X 10.5 Leopard.

User reports: The problem was SOLVED by simply moving the System Preferences/Keyboard and Mouse double-click setting off full right. Faster clicks are not necessarily better. Somewhere between 1/2 and 3/4 seem to work great. Do not run with the setting advanced to the max.

4) Need password to access Entourage after Leopard install

Option 1: This has to do with the keychain being replaced. If, in the dialog you were presented with, you checked 'add to keychain', the new password should stick again, and this should be a once-only request (it was for me). If it doesn't stick, open the keychain and run 'keychain first aid' from the 'keychain access' menu. That should put any problems right.

Option 2: After you install Leopard, you might find that your default administrator (admin) account has become a standard account. If there are no other admin accounts on your computer, there’s no easy way to get your administrator powers back. You’ll need to restart in single-user mode (holding down the Command-S key during startup) and follow the prompts to type the commands needed to gain write access to the drive. After doing so, type rm /var/db/.AppleSetupDone (note the space between rm and /var) and press return. Next, type reboot and press return to restart your Mac.

You will arrive at the Setup Assistant screen, the screen that appears when you first set up a new Mac. From here, create a new account (using a different name than your old account). After logging in to this new account, which should be an admin account, go to the Accounts preferences pane, select your original account, and select the Allow User To Administer This Computer option. Log out and log back in to your original account. If you’d like, now you can select the new account you created here and delete it.

5) Entourage 2004 unable to connect securely to Exchange 2003 server. Error "Unable to establish a secure connection to <servername> because the root certificate is not installed.

User reports: After much frustration I finally have Entourage making an SSL connection to an Exchange server in Mac OS X Leopard after performing the OS Leopard installation from scratch.

All that is needed is your root certificate - no private key, no digital identity

Now do the following:

1. Put the root certificate in your home folder.
2. Open a terminal.
3. Type the following:

sudo certtool i root_certificate.cer v k=/System/Library/Keychains/X509Anchors

Obviously replacing "root_certificate.cer" with your certificate filename.

The last line of output should read "...certificate successfully imported." If you get an error saying that the certificate is in the wrong format and needs to be in PEM format, then use the Microsoft Cert Manager to convert the certificate format by importing then exporting as PEM.

User explanation: Why did it break?

As it turns out, the X509Anchors file, as of Leopard, has been made obsolete - but not entirely... It can (and is) still read from, but cannot be written to - at least not with any GUI interface like Apple Keychain or Microsoft Cert Manager.

As Entourage looks at this X509Anchors file for the Root Certificate and not in the new SystemCA/RootCertificates.keychain files, of course it's not going to find it! This also explains why people that upgraded rather than fresh installed did not encounter this age old problem again.