Mac clients using Entourage and Outlook experiencing delayed email

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B

Brian Whaley

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?
 
R

Ripu Daman

Hi,

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.

Ripu Daman Mina | MCSE 2003 & MCSA Messaging
 
B

Brian Whaley

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

Brian Whaley

I've posted it there as well, but I would appreciate any suggestions from anyone here as well. Could it possibly be an issue with the account on the server? I think it's a client side issue as well, but with two completely different versions of the email client having the same issue...
 
G

Gavin-Zhang

Hi Brian,
Sorry about no familiar with the entourage.
Some suggestion for you:
1. Which version for your entourage, it is recommended that update it to 13
2. Also check the CERT whether is properly on MAC box
Some related information here.
Regards!
Gavin
 
C

ClevSparrow

Is there anything in common with the mail that is being delayed? For example, large attachments? To confirm, some email is delivered as expected whereas other messages are significantly delayed and also only for some but not all EWS ? Strange since OWA and the iPhones get the problematic email properly and I that at least the iPhone must use Web Services to communicate with the Exchange server. Could the email be delayed by some anti-virus/filtering on the server (and only because of the information moving by way of Web Services)?

Sorry for more questions than answers. We have not transitioned to Exchange 2010 and have a mixed environment of Macs and PCs as well so I have a dog of sorts in this question.
 
B

Brian Whaley

Hi Brian,
Sorry about no familiar with the entourage.
Some suggestion for you:
1. Which version for your entourage, it is recommended that update it to 13
2. Also check the CERT whether is properly on MAC box
Some related information here .
Regards!
Gavin It's happening with Entourage EWS (latest version) and with Outlook 2011 for Mac as well. The cert is a new one, and is working without issue. Like I said, this is only affecting a small number of people.
 
B

Brian Whaley

No large attachments, there seems to be no rhyme or reason to the delays, just some email is delayed for no obvious reason.

Our spam filtering happens before it ever hits the Exchange box, so no issue there.
 
C

ClevSparrow

Have you tried setting up the Exchange account in Outlook 2011 or EWS in a different Mac OS X account on the same Mac or on a different Mac to see if issue occurs outside the user's normal working account environment?
 
S

Shawn-B

Shot in the dark, but do you have a firewall between the Entourage/Outlook clients and the client access server? We ran into issues with our Outlook 2007 clients (directly connected...not using cached mode) not updating correctly because the firewall keep alive time for TCP connections was set too low.
 
B

Brian Whaley

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.
 
J

JRVA_Q

Brian, any updates to this issue from Microsoft? Also, was this issue present with sp1?
 
B

Brian Whaley

They were supposed to have a Level II support tech call me to advise on a workaround, but that was 2 weeks ago. I plan to call them back next week to follow up, and if I find that the workaround does indeed work, I'll let you know.
 
J

JRVA_Q

Brian, that would be great. I've seen this issue mentioned in other forums but no solution has been offered. I tend to think the problem is at the mailbox level and not a server issue because with our organization, it's only been reported by a few users.
 
G

Graham Wells

Brian, do you have an incident number or the like with MS? Our rep is not able to find anything related to this on their end and we have at least one user who is having the same problem.

Graham
 
B

Brian Whaley

I have the subject line of the escalation email, maybe that will help.

[REG:110110456442329] <Escalation> Outlook 2011 clients are delayed in mail delivery from Exchange 2010

I'm dealing with Pawan Kapoor, Support Escalation Engineer, Office for Mac 2011, Macintosh Enterprise Business Applications | Microsoft&reg; Corporation
 
T

Tyler_E

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.

&ldquo;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.&rdquo;

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.

Great post Brian and thanks!

[REG:110122112152206]

-Tyler
 
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