Mac using Entourage and Outlook experiencing delayed email

[guest]

We recently transitioned to Exchange 2010 (14.01.0218.013), which is running on Server 2008 R2, single machine, no DAG (it's a small user group, 100 email accounts). We have a mixed environment of Mac and PC users. We have a small number of Mac users (3-4) that are experiencing a delay receiving some, but not all, email (anywhere from a few hours to a day) when they use Entourage EWS or Outlook 2011 for Mac. However, they get the emails as expected on their iPhones and using OWA.

When they were still on Entourage EWS, I deleted their local accounts in Entourage and rebuilt them, no change. So, we upgraded them to Outlook 2011 without importing anything from Entourage, no change there either, they still have delayed email.

Obviously this is a problem we need to resolve sooner rather than later, any ideas?

[guest]

Update (11/1/2011): This issue has been fixed in Exchange 2010 SP1 RU6, see KB:2449266 for details. There is no need for customers to call in to request the fix anymore. Just download & install Exchange 2010 SP1 RU6 to fix this issue.

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Update (7/18/2011): The public KB article is now available for this issue, http://support.microsoft.com/kb/2449266. Microsoft is working to fix this issue on a permanent basis. The permanent fix will be released in an upcoming roll up update for Exchange 2010. I will update this post when that information is available. The KB article will also be updated with that info.
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The issue that you experience in Entourage-EWS or Outlook 2011 for Mac (EWS client requests for an item, which results in content conversion on server side), is actually due to a known issue in Exchange 2010 (content conversion fails, connection dropped by server without any response to client).

There is a fix (IU = Interim Update) available for this issue. Customers experiencing this issue should call Microsoft Support (1-800-Microsoft) to request that fix. At this point, it's not planned to be released as part of an update. Calling in and creating a support case to request an IU (Interim Update, see details here: http://technet.microsoft.com/en-us/libr ... 37979.aspx) is required as if at any time in future, Microsoft recalls that fix/IU due to any reason, we will be able to contact those customers to inform them about the recall. Also IUs are Roll Up Updates specific, so you'll need an IU that works well with your current RU level (i.e. specific build).


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Sr. Program Manager, Product Quality, Exchange Client Access Server

[guest]

It clearly a client end issue may be due to account are configure in cached mode, try removing the cache mode & check if the issue still remains or not.

[guest]

I have Outlook 2011 (Mac) and I don't see where the setting is to use cached Exchange mode.

[guest]

Just got off the phone with Microsoft, it's a bug in Exchange 2010. They are aware of the problem, it's caused by dropped TCP connections, and they are working on it.

[guest]

I have had the exact same problem with a 2010 Server running SP1 with no RollUp's applied. I have been given the following information from Microsoft.

“Outlook 2011 synchronization issues you are experiencing when connected to an Exchange 2010 mailbox. While investigation with collaboration with Exchange escalation resource we have found that the issue arises when server fails to convert the item to MIME.”

Luckily I did not have the RU’s installed on the server as there is an existing Interim Update available if you do not have RU2 installed. As Brian pointed out they are still working on an IU that can be applied to RU2 installations. I have the IU from Microsoft and will be installing that on the problem 2010 server tonight, so I guess we will see what happens. If you are in this situation (Exchange 2010 SP1 with no RU’s) you will need to call Microsoft and open a case. They will then be able to send you the IU and a password to download it.

[guest]

I received the hotfix on Friday and installed immediately....I had oan open case from MS about this issue..


It has definitely fixed the problem....We only had 2 users affected out of 85, but all users (in my testing) have been receiving emails faster...We are using Outlook 2011 exclusively and iOS devices.


Be careful when downloading, ONLY download form the server from where it will be installed. I downloaded from home and it got corrupt and errored out on the Exchange Server...Re-downloadig from the Exchange 2010 server fixed it though.


I have the hotfix that was applied to SP1 RU2, there is a different (so I hear) hotfix for SP1 RU1...


Here is the name of the hotfix: KB2449266. It also comes along with an .exe called "sn". This must be run from the command line to disable strong name verification before installing the .msi...

So far, all is well with our Exchange 2010 - Win2008R2....

[guest]

Thanks for confirming that the patch works. We will be installing the ru2 hotfix this weekend. I've never been a fan of these "one off" hotfixes. What will happen to the updated files when we install ru3? Do we have to uninstall this to even be able to upgrade to future ru s or sps? It's also a little fishy that this issue seems to affect all large ews deployments but only a few mailboxes within these organizations. What is unique about the affected mailboxes and why can't they be fixed directly instead of installing this patch that affects everyone?

[guest]

All good questions.....I have installed other hotfixes on the old Exchange 2003 for specific problems only affecting a few users w/o experiencing any issues to the other users....So we will see....

Be aware, the update takes some time (20mis) and DOES turn off some non-Exchange related services like Acronis Imager (and others) for the time being....We did not experience ANY interruptions to any email features...We do not use this server for any other purpose than Exchange though.

As for when MS updates to SP2(?) or RU3(?) I am not sure, but take a look below...(Last sentance) It looks like this Interim Update will have to be UNINSTALLED when a new, offical MS update comes our way....That is if these changes are incorporated in the next SP or RU candidate....I will certanly ask my MS Rep before I close this case:

Note: This Interim Update can only be applied to the same Exchange Server 2010 version and/or Rollup target for which it was intended.
Note: Only one Interim Update can be run on a server at a time. You must remove any other Exchange Server 2010 Interim Update before installing this Interim Update. If you require multiple Interim Update fixes, these Interim Update fixes must be in a single Interim Update
package and need to be requested.
Note: The Strong Name tool (sn.exe) must be present to configure the system to skip strong name verification before installing the Interim Update package.
Note: Strong named signing verification must not be enabled if an Interim Update is present on the server or some services may crash on startup.
Note: You must remove this Interim Update package before installing any Exchange Server 2010 official rollup or alternate IU release.

I hope to close this case this week, pending testing and will report back about the last sentence after the MS Rep comments.....

[guest]

Just an update to this issue. We installed kb2449266 for Ru2 over the weekend on our CAS servers. It's too soon to tell if this has resolved the issue completely since we need to rely on our EWS users to let us know (Mac users are a "special" breed). Our support engineer on the case confirmed that the March Sp1 RU3 WILL have this hotfix included. Hopefully that will put this issue to rest for good.