Q: Exchange servers and Mavericks Mail

Hi Scottr1969,

From my testing, Exchange Server 2010 SP3 RU4 will have issues with Mac Mail. Your best bet is to go IMAP/SMTP until OSX 10.9.2.  Or, if you have the resources, upgrade to Exchange 2013.  Though, most of us are waiting for Microsoft to release Exchange 2013 SP1 so that we can install it on Server 2012 R2.  Right now latest release Exchange 2013 is not compatible with latest release Server 2012 R2...Go figure...

Check to make sure that your Outgoing Mail Server (Under Accounts tab > Account Information) is set to the name of the account profile followed by (Exchange).  For example if your Account profile is called ACME Company then should show: ACME Company (Exchange). When the acocunt name is suffixed with (Exchange) it means you're not using SMTP, but instead going through EWS when sending email.

Also, something else that I've noticed. Mac Mail/Exchange EWS is terrible at synchronizing on slow, highly latent networks.

<Edited by Host>

Hi Jay,

Regarding the calendaring issue.  Is that an Exchange 2010 server?  If so, make sure you have at least RU3 installed.  RU3 fixes a problem with IIS processes crashing due to EWS calendaring traffic.  More details here: KB2888911 W3wp.exe crashes when you decline a meeting request by using Outlook Web App or an EWS application in an Exchange Server 2010 environment.http://support.microsoft.com/kb/2888911

I'd wait for 10.9.2 before building a CAS.

Scottr1969,

Forgot to mention, great find on a post to disable EWS throttling policies: https://migrationwiz.zendesk.com/entries/20006062-How-do-I-disable-the-Exchange- 2010-throttling-policy. Thanks for posting that!

Mail 7.2 build 1865.1 still unable to send attachments via Exchange mail

Hello acurruthers,

I understand. The issue is most likely with your Exchange server.

Which version of Microsoft Exchange?

Which SP and CU do you have installed on the Microsoft Exchange?

Have you configured EWS and IIS yet?

Thanks

The issue is quite likely to be mavericks mail otherwise waiting for 10.9.2 would be pointless - surely?

My experience is closer to bradhs's

I have never found a problem with Mac Mail (any version) and Exchange that could not be fixed by fixing the Exchange Server, when I do it will be a first.

I just found this out.

I sent an email to a customer.

It showed still sitting in my outbox.

I got a reply from my customer, but the email still showed in outbox.

So they got it,  but it still showed like it had not been sent  yet.

Weird.

acarruthers is running a "special" build of Mac Mail and is having issues with attachments.  Those issues are not related to Mac Mail but instead to the configuration of EWS and IIS.  Csound1 is concurring I believe.

Interesting, half of the people that have contacted me had an issue with the way their Exchange server was setup which led to Mac Mail not functioning properly.  It's not that they were configured "wrong" it's just that they were not configured to support the needs of a full blown EWS-based application.  That's probably the best way to put it.

I am quite happy to accept bad Exchange setup may be the cause, so why on earth are we waiting for 10.9.2 unless it is a version that is more tolerant of bad exchange setups? And why was 10.8.x mail also apparently tolerant of the same bad exchange servers?

Can I presume the other half was down to 10.9.1 then?

One was on Exchange 2003, which does not support EWS.  The rest are having an issue with 10.9.1, myself being one of them.

So far, everyone with 10.9.1 bug issues are on Exchange 2007 and 2010.

We have a few hundred Mac users on Exchange 2013 with no issues at all.  We are waiting for Exchange 2013 SP1 to release before we upgrade our mail servers.

Hi Brad,

On the Exchange 2013 setup, is there any possibility that the correlating improvement / stability of synchronizing the OS X systems running Mail is related to running on newer faster hardware with less processing / memory / network load?

-Jay

Hi Bowen,

To be honest, I'd love to have an alternate groupware platform in the mix, but I'm not in a position where I can make that kind of hard shift without dedicating more time than I have available to get it documented to the point that the principles I report to would feel comfortable supporting it.

I'll keep it in mind though.

Thanks,

Jay

Simply said: Exchange synchronization worked just fine with Mountain Lion and didn't ever again immediately after installing Mavericks (not withstanding, according our sys admin, some necessary work arounds going back to our first Mac integrations with Snow Leopard). And I think I can say the same for hundreds, thousands, probably at least tens of thousands. I and our sys admin don't have the time to try to figure this out for ourselves. We shouldn't have too. We just want Mavericks to work in the same manner as prior OS X. And as much as I appreciate all those with suggestions trying to help, I also read again and again in this discussion that even suggestions that work, only work for a matter of days or weeks.

Apple, if you read these posts on your own forum, and I assume you do despite any overt evidence, please fix this issue in 10.9.2. Thank you!

Hi Jay,

I don't believe so, I think Mac Mail is just plain broken in 10.9.1 with certain versions of EWS.  We have a bunch of Exchange servers, some on very similar--identical even--equipment/technologies.  I have seen all kinds of issues, including routers with screwed up NAT rules.

I'm sure you already know this, there's so much that goes into an Exchange server, you can set it up and think you've got it configured for all situations, then stuff like this happens.

EWS is a great platform for applications to interface, if Microsoft would invested more time and effort into EWS they could have also switched Outlook on Windows to it.  But they don't, and I have no idea why.   I can't understand why they would want to keep RPC going when they can do it all through EWS.