Messages Not All Syncing

[clayjohanson]

Hi all,

Here's what I have:

SBS 2008 with Exchange 2007
Vista machine running Outlook 2007 (all service packs and updates)
Multiple Macs running Entourage 2008 (all service packs and updates)

Each Outlook/Entourage syncs to the same mailbox on the Exchange
Server. But just within the past couple of days, I have noticed that
Entourage does not sync ALL messages within a folder, for several
large folders. For example, my Sent Items folder contains 6925 items.
Here's what I see:

Using OWA: 6925 items
Using Outlook 2007: 6925 items
Using Entourage 2008 on TWO different machines: 6855 items

Other folders have similar discrepancies... 800 (OWA/Outlook) vs. 780
(Entourage), for example. There are no error messages received at any
time and I've even reproduced the issue with a test mailbox I created
(created mailbox, importes messages). It appears that Entourage is
just having problems syncing all of the messages. I don't know if this
problem started recently or if it's been going on for a while and I
just never noticed.

Does anyone have any ideas?

Thanks!

 

[jlmarr53]

Hi all,

Here's what I have:

SBS 2008 with Exchange 2007
Vista machine running Outlook 2007 (all service packs and updates)
Multiple Macs running Entourage 2008 (all service packs and updates)

Each Outlook/Entourage syncs to the same mailbox on the Exchange
Server. But just within the past couple of days, I have noticed that
Entourage does not sync ALL messages within a folder, for several
large folders. For example, my Sent Items folder contains 6925 items.
Here's what I see:

Using OWA: 6925 items
Using Outlook 2007: 6925 items
Using Entourage 2008 on TWO different machines: 6855 items

Other folders have similar discrepancies... 800 (OWA/Outlook) vs. 780
(Entourage), for example. There are no error messages received at any
time and I've even reproduced the issue with a test mailbox I created
(created mailbox, importes messages). It appears that Entourage is
just having problems syncing all of the messages. I don't know if this
problem started recently or if it's been going on for a while and I
just never noticed.

Does anyone have any ideas?

Thanks!

I've had this problem for a while, but just this week it has gotten
serious to the point where many of my Entourage folders are empty or
not syncing with Exchange at all. This is for both Entourage 2004 on
Tiger and Entourage 2008 on Leopard. As with you the Outlook/Windows
and OWA clients agree on the contents and seem to be up to date. I've
rebuilt the database on both Macs to no avail. Wasn't sure if it was
just me until I saw your message. Now, where to from here?

 

[clayjohanson]

I've had this problem for a while, but just this week it has gotten
serious to the point where many of my Entourage folders are empty or
not syncing with Exchange at all.  This is for both Entourage 2004 on
Tiger and Entourage 2008 on Leopard.  As with you the Outlook/Windows
and OWA clients agree on the contents and seem to be up to date.  I've
rebuilt the database on both Macs to no avail.  Wasn't sure if it was
just me until I saw your message.  Now, where to from here?

I've tried rebuilding my databases as well, with no joy (problem still
occurs). Like I said, I don't know if the problem just started
occurring or if it's been going on for a while, as I wasn't really
looking at the item counts in Entourage and comparing them against the
item counts in Outlook or OWA. Now that I am aware of the problem, I
am ACUTELY aware of it.

Hopefully someone from Microsoft (tech support engineer, MVP) is
reading this and can offer a solution or refer this question on to
someone at Microsoft who can do something about it.

 

[Adam Bailey]

SBS 2008 with Exchange 2007
Vista machine running Outlook 2007 (all service packs and updates)
Multiple Macs running Entourage 2008 (all service packs and updates)

Each Outlook/Entourage syncs to the same mailbox on the Exchange
Server. But just within the past couple of days, I have noticed that
Entourage does not sync ALL messages within a folder, for several
large folders. For example, my Sent Items folder contains 6925 items.
Here's what I see:

Using OWA: 6925 items
Using Outlook 2007: 6925 items
Using Entourage 2008 on TWO different machines: 6855 items

The machines are both missing the same messages? Can you tell which ones are
missing? Anything peculiar about them?

What happens if you control-click the folder and choose Properties > Folder
Properties > Empty Cache?

 

[clayjohanson]

The machines are both missing the same messages? Can you tell which ones are
missing? Anything peculiar about them?

What happens if you control-click the folder and choose Properties > Folder
Properties > Empty Cache?

Already tried emptying the cache, as well as rebuilding the entire
identity, on TWO different machines. The number of missing items for
each particular folder is the same every time (in the case of my Sent
Items folder, it is ALWAYS 70 items). The Exchange Server serves only
one user, me, so there is no chance of it being overburdened or
anything.

And since we are talking about 70 missing messages out of almost 7000,
I would have a very hard time figuring out which are missing. So, no,
I don't know of anything peculiar about any messages that are missing.

Are there any log files anywhere that you know of that log Entourage's
sync process?

 

[Adam Bailey]

Already tried emptying the cache, as well as rebuilding the entire
identity, on TWO different machines. The number of missing items for
each particular folder is the same every time (in the case of my Sent
Items folder, it is ALWAYS 70 items). The Exchange Server serves only
one user, me, so there is no chance of it being overburdened or
anything.

When you rebuild the cache, Entourage loses all information about what
is on the server and asks for a fresh copy. Which suggests that
Entourage is having trouble accessing those specific messages. They may
be corrupt.

That said, I also don't recommend keeping 7,000 messages on a server.
Email servers are not meant to be a long term repository. I recommend an
offline archive and bring your email more current. Entourage has been
known to have difficulty syncing with very large message stores.

And since we are talking about 70 missing messages out of almost 7000,
I would have a very hard time figuring out which are missing. So, no,
I don't know of anything peculiar about any messages that are missing.

Actually I don't know that it would be so hard if you sort your messages
in groups, perhaps organized by Date or Sender.

Are there any log files anywhere that you know of that log Entourage's
sync process?

If there was an error you'd be notified.

 

[TomC]

There have been other posts regarding problems with Entourage synching
email folders with the Exchange server. For example,

http://groups.google.com/group/micr...&q=email+folder+synching+owa#1e565055be23c224

Although strategies such as clearing the cache in an Entourage folder
can temporarily fix a problem, long term it does not. No matter what
you do, if you send messages via OWA, they will not later appear in
your Entourage sent folder, for example. I believe I read somewhere on
the forum that MBU is aware of this issue but it is unclear what the
source of the problem is or if a permanent fix is forthcoming.

I am talking way above my job description here and hopefully some of
our generous (with their time and expertise) MVPs will have the full
story.

 

[Adam Bailey]

No matter what you do, if you send messages via OWA, they will not
later appear in your Entourage sent folder, for example.

This may be happening in some cases, but I want it to be clear for the
record that this is by no means universal. I've never had this
particular problem.

 

[clayjohanson]

This may be happening in some cases, but I want it to be clear for the
record that this is by no means universal. I've never had this
particular problem.

Thanks for the feedback. I'll keep an eye out for the OWA issue.

As a former Microsoft tech support engineer (I worked there for over
10 years in Excel, Office, and Outlook support -- look me up in the
Knowledge Base under "clayj"), I understand that sometimes only
workarounds are available, not real solutions. Taking the e-mail off
of the Exchange Server and putting it into offline stores is a
workaround, not a real solution, because doing so would prevent me
from being able to access all of my e-mail from any machine I happen
to be using. Exchange Servers *are* intended to used for long-term
message storage; check with any Microsoft employee and they'll tell
you that that's the ONLY way they're allowed to keep mail at work.

I've got one mailbox, to which are connected Outlook 2007 on two
machines and Entourage 2008 on three machines, not to mention an
iPhone which is syncing via ActiveSync. The whole reason for having
the Exchange Server was to serve as a single repository which all
devices and machines could use to store the mail on. Each e-mail
client caches the mail from that server, so that I don't have to worry
about making changes to multiple machines independently; any change
that I make in one e-mail client should be synced up to the server and
then synced down to all of the other machines.

Based on the feedback that Entourage frequently has issues syncing
very large folders, I must come to the conclusion that Entourage
simply isn't a very good Exchange client, particularly not in large
organizations or where users may have large mailboxes. I'd appreciate
it if someone from Microsoft would make sure that this issue of
failure to properly sync is addressed soon in a new build of Entourage
2008; there is no good reason why Entourage should be skipping
messages in a folder when it's synced.

Thanks.

 

[Ed Kimball]

Thanks for the feedback. I'll keep an eye out for the OWA issue.

As a former Microsoft tech support engineer (I worked there for over
10 years in Excel, Office, and Outlook support -- look me up in the
Knowledge Base under "clayj"), I understand that sometimes only
workarounds are available, not real solutions. Taking the e-mail off
of the Exchange Server and putting it into offline stores is a
workaround, not a real solution, because doing so would prevent me
from being able to access all of my e-mail from any machine I happen
to be using. Exchange Servers *are* intended to used for long-term
message storage; check with any Microsoft employee and they'll tell
you that that's the ONLY way they're allowed to keep mail at work.

I've got one mailbox, to which are connected Outlook 2007 on two
machines and Entourage 2008 on three machines, not to mention an
iPhone which is syncing via ActiveSync. The whole reason for having
the Exchange Server was to serve as a single repository which all
devices and machines could use to store the mail on. Each e-mail
client caches the mail from that server, so that I don't have to worry
about making changes to multiple machines independently; any change
that I make in one e-mail client should be synced up to the server and
then synced down to all of the other machines.

Based on the feedback that Entourage frequently has issues syncing
very large folders, I must come to the conclusion that Entourage
simply isn't a very good Exchange client, particularly not in large
organizations or where users may have large mailboxes. I'd appreciate
it if someone from Microsoft would make sure that this issue of
failure to properly sync is addressed soon in a new build of Entourage
2008; there is no good reason why Entourage should be skipping
messages in a folder when it's synced.

Thanks.

Clay, you've hit the nail on the head:

I must come to the conclusion that Entourage
simply isn't a very good Exchange client

The best way (such as it is) to contact MS with requests or suggestions is
via Send Feedback to Microsoft on any of the Office Help menus. I would hope
that the opinion of a former tech support engineer would carry a little more
weight than those of us ordinary old users.

 

[Corentin Cras-Méneur]

Based on the feedback that Entourage frequently has issues syncing
very large folders, I must come to the conclusion that Entourage
simply isn't a very good Exchange client, particularly not in large
organizations or where users may have large mailboxes.

Out of curiosity, have you tried the Entourage EWS public beta?
http://is.gd/gzVL


Corentin

 

[Jack Marr]

Out of curiosity, have you tried the Entourage EWS public beta?http://is.gd/gzVL

I'd like to try that, but one of the prerequisites is this: "You must
be connecting to Exchange Server 2007 with Service Pack 1 with Update
Rollup 4 or later." How do we determine that? I can see via OWA a
number of things About the Exchange Server, e.g. "Mailbox server
Microsoft Exchange version: 8.1.240.0". Does that correspond to to
the prereq?

 

[Corentin Cras-Méneur]

I'd like to try that, but one of the prerequisites is this: "You must
be connecting to Exchange Server 2007 with Service Pack 1 with Update
Rollup 4 or later." How do we determine that? I can see via OWA a
number of things About the Exchange Server, e.g. "Mailbox server
Microsoft Exchange version: 8.1.240.0". Does that correspond to to
the prereq?

8 is exchange 2007, .1 is SR1 and 240.0 is the build number. I'm not
sure exactly which rollup it is though but it should be fairly close.
I have 336.0 and it corresponds to rollup 5.

Corentin

 

[clayjohanson]

Out of curiosity, have you tried the Entourage EWS public beta?http://is.gd/gzVL

Corentin

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I didn't know about EWS... very cool! I will see about installing it
on one of my Macs and will report back with my findings.

Thanks!

 

[Jack Marr]

8 is exchange 2007, .1 is SR1 and 240.0 is the build number. I'm not
sure exactly which rollup it is though but it should be fairly close.
I have 336.0 and it corresponds to rollup 5.

I should have read further down the link you provided earlier -
amongst the comments is this list of Exchange version numbers and
version "names":

Exchange 2007 SP1 RU5 - 8.1.336.1
Exchange 2007 SP1 RU4 v2 - 8.1.311.3
Exchange 2007 SP1 RU4 v1 - 8.1.311.1
Exchange 2007 SP1 RU3 - 8.1.291.2
Exchange 2007 SP1 RU2 - 8.1.278.2
Exchange 2007 SP1 RU1 - 8.1.263.1
Exchange 2007 SP1 - 8.1.240.6
Exchange 2007 RU7 - 8.0.813.0
Exchange 2007 RU6 - 8.0.783.2
Exchange 2007 RU5 - 8.0.754.0
Exchange 2007 RU4 - 8.0.744.0
Exchange 2007 RU3 - 8.0.730.1
Exchange 2007 RU2 - 8.0.711.2
Exchange 2007 RU1 - 8.0.708.3
Exchange 2007 - 8.0.685.25
Exchange 2003 SP2 - 06.05.02.7638
Exchange 2003 SP1 - 06.05.06.7226
Exchange 2003 - 06.05.04.6944

So to answer myself, 8.1.240.0 won't cut it.

 

[Corentin Cras-Méneur]

So to answer myself, 8.1.240.0 won't cut it.

Unfortunately. I believe it has bugs with the WebServices that affect
Entourage greatly :-\

Corentin

 

[Jack Marr]

As it turns out, this is a known problem caused by a bug preventing
Entourage from not being able to receive Exchange emails in which the
Subject contains a plus sign (+). The issue was discussed in this
thread:

http://groups.google.com/group/micr...?hl=en&lnk=gst&q="plus+sign"#ff3068f4bddbf073

And in that thread there's a link to a blog that has a work-around:
http://tinyurl.com/5ltnae

The OP Clay has determined that the work-around solves the problem for
him - I'll need to negotiate with our sysadmins. But I'm wondering if
anyone knows if this issue has been solved in a later release of
Exchange? We're running 8.1.240.0. Upgrading might be a more
palatable solution to our sysadmins.

 

[clayjohanson]

As it turns out, this is a known problem caused by a bug preventing
Entourage from not being able to receive Exchange emails in which the
Subject contains a plus sign (+).  The issue was discussed in this
thread:

http://groups.google.com/group/microsoft.public.mac.office.entourage/...

And in that thread there's a link to a blog that has a work-around:http://tinyurl.com/5ltnae

The OP Clay has determined that the work-around solves the problem for
him - I'll need to negotiate with our sysadmins.  But I'm wondering if
anyone knows if this issue has been solved in a later release of
Exchange?   We're running 8.1.240.0.  Upgrading might be a more
palatable solution to our sysadmins.

I can confirm now that following the workaround has solved the problem
completely. All of my Entourage 2008 installations are now properly
syncing all messages from Exchange 2007. Once the steps were performed
on the Exchange Server, the unsynced items automatically showed up in
Entourage without any additional work required.

FWIW, my Exchange 2008 is at the very latest rev right now,
8.01.0336.000. I don't see any downside to following the steps in the
workaround.

Thanks, Jack!

 

[clayjohanson]

Sorry, that should have been Exchange 2007, not 2008.