Entourage not syncing sent items back to Exchange server

[John Cradock]

For some reason my Entourage 2008 is not syncing sent items back to my
Exchange server. Items I send with Apple Mail and from my iPhone appear in
the sent items if I log into my Outlook Web Access, but items sent from
Entourage are not showing up. Any ideas?

 

[William Smith [MVP]]

For some reason my Entourage 2008 is not syncing sent items back to my
Exchange server. Items I send with Apple Mail and from my iPhone appear in
the sent items if I log into my Outlook Web Access, but items sent from
Entourage are not showing up. Any ideas?

This could be a couple of things.

Many folks find that clearing the Sent Items folder cache often takes
care of the problem. First, duplicate your Sent Items so that you have a
backup. Next right-click or Control-click the Sent Items folder, select
Folder Properties and click the Empty button to empty the cache.

Restore missing messages from your backup by dragging them back into the
Sent Items folder.

If this doesn't work then you're possibly part of a small group of folks
who are having chronic problems with syncing the Sent Items folder with
Exchange. I don't think enough of these folks have come together to get
Microsoft's attention. I tried one time but had little interest. Most
folks were using Exchange Server 2003 and Entourage 2008.

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[John Cradock]

William Smith wrote:

This could be a couple of things.

Many folks find that clearing the Sent Items folder cache often takes
care of the problem. First, duplicate your Sent Items so that you have a
backup. Next right-click or Control-click the Sent Items folder, select
Folder Properties and click the Empty button to empty the cache.

Restore missing messages from your backup by dragging them back into the
Sent Items folder.

If this doesn't work then you're possibly part of a small group of folks
who are having chronic problems with syncing the Sent Items folder with
Exchange. I don't think enough of these folks have come together to get
Microsoft's attention. I tried one time but had little interest. Most
folks were using Exchange Server 2003 and Entourage 2008.

It's weird. As you suggested, I backed up the contents of my Sent Items in
Entourage, then cleared the cache for this folder, then moved back some of
the items that were missing. Once I moved them back, these items did sync
back to the Sent Items on the Exchange server. However, when I then sent a
message from Entourage, that message never synced to the server. I am using
Entourage 2008 and Exchange 2007.

 

[William Smith [MVP]]

It's weird. As you suggested, I backed up the contents of my Sent Items in
Entourage, then cleared the cache for this folder, then moved back some of
the items that were missing. Once I moved them back, these items did sync
back to the Sent Items on the Exchange server. However, when I then sent a
message from Entourage, that message never synced to the server. I am using
Entourage 2008 and Exchange 2007.

Are you up for a second experiment?

I'd like to know what happens when you have a completely empty Sent
Items folder. Possibly one of the messages in the Sent Items folder gets
some corruption and is stopping the sync process somehow.

Can you follow the steps again to backup your Sent Items folder and
clear the cache? This time, don't return any messages to the Sent Items
folder. Wait for the messages to sync from Exchange.

Now, create a new mail folder and call it something like "Sent Items
(Old)". Move all your Sent Items messages to that folder so that your
Sent Items folder is now empty.

Continue using Entourage normally for a while, allowing your newly sent
messages to begin populating your Sent Items folder.

Try comparing this folder with what you see either in Outlook or OWA on
a daily basis. As soon as you see the problem occur again, note the last
message synced and the next message that didn't get synced.

Anything unusual about that message? Did Entourage generate the message
or possibly Outlook or a mobile device?

By the way, I encourage folks to connect to their backend server
whenever possible. Can you tell me how you're connecting? I have details
here in this blog post:

"Optimize Entourage to better work with Exchange"
<http://blog.entourage.mvps.org/2008/03/optimize_entourage_to_better_work_with_exchange.html>
or <http://tinyurl.com/56ea7k>.

Thanks, John!

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[John Cradock]

William Smith [MVP] wrote:

Are you up for a second experiment?

I'd like to know what happens when you have a completely empty Sent
Items folder. Possibly one of the messages in the Sent Items folder gets
some corruption and is stopping the sync process somehow.

Can you follow the steps again to backup your Sent Items folder and
clear the cache? This time, don't return any messages to the Sent Items
folder. Wait for the messages to sync from Exchange.

Now, create a new mail folder and call it something like "Sent Items
(Old)". Move all your Sent Items messages to that folder so that your
Sent Items folder is now empty.

Continue using Entourage normally for a while, allowing your newly sent
messages to begin populating your Sent Items folder.

Try comparing this folder with what you see either in Outlook or OWA on
a daily basis. As soon as you see the problem occur again, note the last
message synced and the next message that didn't get synced.

Anything unusual about that message? Did Entourage generate the message
or possibly Outlook or a mobile device?

By the way, I encourage folks to connect to their backend server
whenever possible. Can you tell me how you're connecting? I have details
here in this blog post:

"Optimize Entourage to better work with Exchange"
<http://blog.entourage.mvps.org/2008/03/optimize_entourage_to_better_work_with
_exchange.html>
or <http://tinyurl.com/56ea7k>.

Thanks, John!

Thanks for the additional suggestions. Sure, I'll try this and see if it
helps.

Also, I pretty much always connect via http since I'm never in my office,
and doing it over a VPN connection is too much of a hassle.

 

[William Smith [MVP]]

Thanks for the additional suggestions. Sure, I'll try this and see if it
helps.

Also, I pretty much always connect via http since I'm never in my office,
and doing it over a VPN connection is too much of a hassle.

Good to know. Thanks, John!

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>