Exchange servers and Mavericks Mail

Hi Cuttergot,

It's stuck in the outbox because the Exchange server is severing the connection causing a time-out. Call up your IT company and ask them to adjust EWS and IIS settings.

Here's some proof that the issue is real and it is the Exchange server: http://stackoverflow.com/questions/10091745/exchange-web-services-attachment-loa d-is-slow

Here's more info:

http://msdn.microsoft.com/en-us/library/office/jj945066(v=exchg.150).aspx

http://blogs.msdn.com/b/mstehle/archive/2010/11/09/ews-best-practices-understand -throttling-policies.aspx

Let me save you some time... Since you're going to Outlook for Mac here's an article that you'll need to read to try and solve this same problem with Outlook for Mac, this is from the Outlook forum: http://social.technet.microsoft.com/Forums/en-US/1d1eadc2-db89-4147-bd9c-38a1435 1ce8e/slow-attachment-upload-with-exchange-web-services-outlook-2011-for-mac?for um=exchange2010

Also, look back at my previous posts, send that information to your IT company.

All,

Going forward, to help us troubleshoot, please include on the top line of your post/replies the following:

1) Version of Microsoft Exchange, if you know the SP and ** levels, please provide that information too.

2) Version of OS X? 10.9.1 I assume.

3) If you have Autodiscover selected or if you have to manually select your mail servers.

4) Is your Exchange Server hosted offsite or at your office?

5) Are you having issues while at the office and/or out of the office?

Hi Bradhs,

many thanks for your support and advise.

Well, all other mac users in our company that use outlook do not have that issue. So it is either related to my mac itself or to mail.

I will see today if the issue shows up with Outlook too.

thanks

-chris

Hi Chris,

I agree, keep in mind Outlook for Mac and Outlook for Windows use completely different methods to communicate with Exchange. Outlook for Mac uses a newer method called EWS while Outlook for Windows uses the older RPC/HTTPS.

If your IT people need any help please ask them to post here and I'll see what I can do. The beginning of my address is bradish75.

And the domain is hotmail.

I know this post is old but some of you might be running unpatched servers on the backend. Here's the post: http://social.technet.microsoft.com/Forums/exchange/en-US/352776de-ab8a-400f-9f0 9-fb13cfa89f52/mac-clients-using-entourage-and-outlook-experiencing-delayed-emai l?forum=exchange2010

Also, if there are any load balances in use there could be an issue with TCP timeouts on the firewall.

Here's a list of all the difference versions and patches of Exchange, this can be helpful to provide to IT in an effort to get them to install the most recent updates: http://social.technet.microsoft.com/wiki/contents/articles/240.exchange-server-a nd-update-rollups-build-numbers.aspx

Bradhs interesting to read about MS patches to Exchange, but how do you explain cases where all the problems experienced with Mavericks are cured by switching to Outlook for Mac?

Points to me as a fragility in Mavericks mail, which is presumably why people on the Seed beta program are reporting that it is now looking rosy and wait for the fix. If the problem was Exchange, why do Apple work on a fix?

Peter,

Do you understand the Exchange is like a continual work in progress, one with so many configuration options it is difficult to even describe a standard setup.

I host my own Exchange server, I never have any issues with any mail client (as posted here before)

IT Depts tend to be lazy, lacking in knowledge, and opposed to Macs.

peter_watt wrote:

, but how do you explain cases where all the problems experienced with Mavericks are cured by switching to Outlook for Mac?

And how do you explain the many users who did not find that Outlook fixed their issue?

Hi Brad,

once again, many thanks for your help and advice. I really appreciate it if peolpe are interested in helping other and keep posting and offering help. That is great! Thank you!

Nevertheless, I received the Office 11 installer later this afternoon, did the install, created an account with autodiscover, and received my emails. Did a test with Outlook, send out an email with 87KB attachment, went out fine. Sent out another email with a 4MB pdf attachment, went out smooth, no issues.

Did the test again with mail, sent out an email with the 87KB attachment... well, it is stuck in my outbox since 2 hours, blocking all my traffic.

Okay, so for me that is clear: will use Outlook from now on.

many thanks again

-chris

It is clear to me, too, that for now Mail won't do with Exchange. I have many of the same problems and have resolved to wait for the Apple fix. I briefly tried Outlook, but gagged at the confusing complexity of it. I was back in Microsoft land. So in the meantime I tried Foxmail, which is free, is available in the Mac App store and works very well with Exchange, including sending attachments. Unlike Outlook, it looks and feels a lot like OSX Mail so I am right at home using it.

I should add that I have not been able to make Foxmail work with the Exchange global address book for my institution. That's a limitation. It is working fine, though with my own contacts saved on the Exchange server.

So while waiting for an Apple fix to you problem, you might want to try Foxmail, too.

Global

Me explain? Well I will explain just one thing. Mavericks mail is a piece of crap needing big fixes for several major errors missed by the first big fix in November.

You don't have the problem. You don't have the solution. So keep out.

Hi Chris,

That's great news! Outlook for Mac does fair better than Mac Mail in Mavericks 10.9.1. Look out for Mavericks 10.9.2 to resolve the issues with Exchange.

Though, the fact that you've had issues with attachments still points to timeout, especially when sending attachments. I believe you'd be better served to have your IT guys up the timeouts and data lengths in EWS and IIS. That will reduce retries and timeouts in all products that communciate via EWS.

Global,

Foxmail looks great!

Csound,

I'm glad to see others on here who have deep Exchange knowledge.

Bradley

Hi Brad,

Some good points and resources....but as someone who administers a number of smaller clients with Exchange, it isn't always ideal to tinker with some of those settings as it can result in a kind of 'butterfly effect'. One change today might result in a logging issues tomorrow, or being susceptible to a DDOS tomorrow.

All told, it appears that Microsoft has the Outlook 2011 product automatically throttle while Apple's 'Supports Exchange' apps...do not do a very good job.

-Jay

Csound1 wrote:

"You don't have the problem. You don't have the solution. So keep out"

Unfortunately you dont get to make those decisions.

I know, it was simply a request. If you can only be smug and condescending, best shut up. I don't think I am alone in that opinion.

JayMMueller is right on the money.

Further, CSound ignores the fact that Apple can be incredibly insular, to the point that internal departments seem impervious to outside information from customers or the customer facing support team, until they are roundly embarassed in public. Even then, they tend to drag heels.

I still love Apple products, but the above, along with serious questions these repeatedly unfixed issues have to lead one to ask about the quality of Apple QA, give me real pause. Exchange support has been seriously broken since Mountain Lion. I reported and escalated what I saw of these issues within a few weeks of its release. Eventually, even going the letter to Tim Cook route, when support seemed clueless and ineffective, then being routed to an executive support person to help me with my concerns. Still, here we are over a year and many point releases later, with a defective product that Apple still claims 'supports Exchange'.

It doesn't. Maybe it will soon. But without violating NDA, let me say that I am not hopeful. Heck at this stage, they haven't even seemed to lick the issue of Mail wanting to download tons of mail messages and attachments it should already have cached, each time it's instantiated. Exchange servers are fickle. But that points to some serious engineering flaws in Mail.

I'll keep writing bug reports. No one seems to be reading them though.

Okay everyone, that was some great reading.

For the newbies to this thread:

Mavericks 10.9.1 does not reliably function with certain versions of Microsoft Exchange. Make sure your IT department has Exchange and the Windows server that it is hosted on fully patched. Latest Service Pack and Commulative Update.

If you're having a timeout issue while sending emails with large attachments please make sure your IT department has properly configured EWS and IIS settings.

If you're having any other problems then please describe it here. You can also wait for OSX 10.9.2 as it will most likely solve issues with Exchange.

In the mean time you can switch to IMAP/SMTP. Exchange fully supports IMAP and SMTP protocols.

Hi All,

I've reading all this discussion about EWS and proper configuration of Exchange to work with Mail. Although in some cases that might solve the issue, in many other it will not.

My firm uses Office 365, so our Exchange server is actually configured and managed in the cloud by Microsoft itself, to work with any mail client. Nevertheless, after upgrading to Mavericks my life in Mail became a nightmare.

Problems include:

(a) the automatic migration of messages is a disaster, so Mail 7 lost all the index and all messages

(b) rebuilding mailboxes did not work so I had to delete the account (its files and indexes in the Library) and recreate the account. I have 20GB of messages, with 100+ mailboxes so on can image how long it takes...

(c) even after all that, Mail still has many problems when syncronizing with Exchange, such as a huge lag, mailboxes with punctuation are always a problem and we don't even get an attachment count anymore.

Unfortuynately, going back to ML will be a bigger pain, as I have already updated third party software like parallels so I either wait for 10.9.2 or switch to Outlook (which also requires more waiting to DL all my mailboxes again and a lot of training).

peter_watt wrote:

Csound1 wrote:

"You don't have the problem. You don't have the solution. So keep out"

Unfortunately you dont get to make those decisions.

I know, it was simply a request. If you can only be smug and condescending, best shut up. I don't think I am alone in that opinion.

Condescension is in the eye of the beholder.