Entourage 2008, Exchange 2003, and Sent Mail synchronization

[MikeTRose]

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: Exchange

There have been several threads on this topic before (the longest at <http://www.officeformac.com/ProductForums/Entourage/2598?@@)>, but I don't think we've ever got a lockdown on the issue. Here's what I'm experiencing, the testing I've done, and a suggested workaround. I'm using E2008 12.1.5 connecting to Exchange 2003.

ISSUE: Some, but not all, Entourage 2008 users who use Exchange 2003 (and possibly 2007) are experiencing 'missing' Sent Items content. Associated conditions may include: having migrated a 2004 identity forward to 2008; having multiple SMTP aliases on the user's Exchange account.

Messages sent from Entourage via Exchange show up in the Exchange account's "Sent Items" folder in Entourage 2008, but do not show up in OWA's sent mail folder or on secondary devices, Outlook, etc. Conversely, mail sent from OWA does not synchronize back to Entourage 2008's Sent Items folder.

This is not a question of confusion over which Sent Items folder belongs to the Exchange account and which one is under the local folders; nor is it resolvable via a Synchronize Now. Mail is really, truly not syncing. I've observed this on multiple machines and with multiple users who have updated from 2004 to 2008.

TESTING: After confirming that mail sent from my primary identity and my primary account was NOT synchronizing to the server-side Sent Items folder, I created a new identity and connected it to two Exchange accounts; first, a pre-existing account, and secondly a just-created test account. ***Both these accounts behaved normally; sent mail synchronized to the Sent Items folder in OWA within 1-2 minutes.***

OTHER OBSERVATIONS (with a hat tip to Rich Rose): Examining the folder properties for the Sent Items and Inbox of the test account vs. my original account revealed an interesting distinction. Screenshot links below. The test account, with an account ID "mtr" and email address beginning with "MTR.Test" shows a folder path of "https://webmail.mydomain.com/exchange/mtr.test/Sent Items <https://webmail.mydomain.com/exchange/mtr.test/Sent Items>" -- exactly what you'd expect. My account, however, is showing a path of "/mrose/Sent%20Items" which is neither my account ID or my canonical email address -- it's an SMTP alias. Same path for my Inbox. Another user who reports the sent items sync issue also shows a secondary SMTP address for his sent mail path.

<http://skitch.com/mike/9am4/sent-items-correct> -- test account/new identity, matches email address, Sent Items sync working

<http://skitch.com/mike/9acb/sent-items-not-syncing-for-this-account> -- my existing account/ID, does not match primary email address, Sent Items sync NOT working

WORKAROUNDS & FURTHER TESTS: My next step is to try a fresh identity with my Exchange account (which I'd been resisting as it will take hours to sync up the mail). Step after that is to file all the sent mail in my existing account, delete Exchange account, and then import old identity local mail into new identity with (hopefully) working Sent Items sync. A big pain. I may also try deleting some of my legacy SMTP aliases.

If there's any possibility of a connection between the OWA folder paths issue and the Sent Items sync, I'd love a way to get control of what paths Entourage uses to define those folders.

If you are also experiencing this issue, please respond below and include the following details:

Version of Entourage? of Exchange?
Did you upgrade your 2004 identity to 2008, or start fresh?
What is the folder path to your Sent Items folder (right-click, Folder Properties)? Does it match your account ID or primary email address?
Have you tested your Exchange account in a new identity?

Thanks,
--Mike

 

[MikeTRose]

Follow up -- a colleague who is NOT experiencing the issue, and has verified her folder paths for me. OWA reports the path to Sent Items with her account ID, and Entourage reports it with her default SMTP address. She also upgraded her identity from 2004 to 2008.

Interesting.

 

[MikeTRose]

Follow-up #2: Creating a fresh identity for my account on another machine (while my local database rebuilds.... *sigh*), I was able to have sent mail synchronize to the server-side Sent Items folder. The URL for my Sent Items in that identity matches my primary email address.

 

[TomC]

Follow-up #2: Creating a fresh identity for my account on another machine(while my local database rebuilds.... *sigh*), I was able to havesentmail synchronize to the server-sideSentItems folder. The URL for mySentItems in that identity matches my primary email address.

Mike,

I have the same problem. Items sent from Outlook or OWA access appear
in Outlook and OWA but are not synched back to Entourage Sent folder.
Items created in E2008 are not synched (or at least not viewable) in
Outlook.

Version of Entourage? => E2008
Version of Exchange? => Unsure, think it is 2003
Did you upgrade your 2004 identity to 2008, or start fresh? =>
Upgraded 2004
What is the folder path to your Sent Items folder (right-click, Folder
Properties)? Does it match your account ID or primary email address?
=> exchange/username/Sent%20items/
Have you tested your Exchange account in a new identity? => No

The "%20" in the path for the Sent folder is suspicious.

Hope there is an easy solution that does not take hours of work
(aren't these supposed to be "productivity tools? ;-)

Tom

 

[William Smith [MVP]]

I have the same problem. Items sent from Outlook or OWA access appear
in Outlook and OWA but are not synched back to Entourage Sent
folder. Items created in E2008 are not synched (or at least not
viewable) in Outlook.

Hi Tom!

A quick question and I'd really appreciate your feedback.

Have you tried emptying your Sent Items cache in Entourage? Follow these
instructions:

1. So that you don't lose your Entourage Sent Items that haven't synced
to Exchange, make a backup of your Sent Items folder or just certain
messages. Do this by dragging the folder or messages to a folder under
"On My Computer".

2. Now, right-click your Exchange Sent Items folder and select Folder
Properties. Click the "Empty" button. This will empty your Sent Items
folder of its messages.

3. Allow enough time for Sent Items to re-sync with Exchange. The amount
of time depends on how many messages are in your Sent Items. Monitor the
progress by watching the Progress window or the activity status
indicator in the lower right corner of the Main Entourage window.

--

bill

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