Exchange servers and Mavericks Mail

I went into my local Apple store and worked with a Genuis, armed with information from this thread, and spoke with several people including the a representative from the business group. After listening to the troubleshooting that I had already done, and documented, I was informed that "Apple is working on an update to solve the problem".

I am running Mavericks 10.9.1. At this time, I am going to wait for the update. One note though, I also have the same problem with Outlook for Mac, even though I have seen several people recommend that as a possible soultion.

I can send email through the same Exchange Server (2007) with Outlook for Windows using Parallels, without a problem with files larger than 8.1mb.

I run into problems with file sizes somewhere between 5.4MB - 8.1MB file size in both Mac Mail and Outlook for Mac. 5.4 will send. 8.1 will NOT.

What I hate the most is that Apple does not publish any best business practices for supporting Mac Mail with Microsoft Exchange.

JayMMueller,

I acknowledge there are definitely issues with Mac Mail and Exchange. Those issues are being actively worked on by Apple. (Still an issue in the latest beta but getting better.)

A best practices guide sounds nice but you could easily google that and find all kinds of useful information on how to conifgure EWS. Also, something you may not know is Microsoft changed the way EWS works by default--many times actually, which is partially the reason you're having problems.

If you are having problems with attachments or emails that contain attachents then it is most likely EWS throttling and timeouts. There are many timeouts that need to be adjusted, can be very dificult getting them all setup properly.

Take a look at these two links:

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

http://www.msexchange.org/articles-tutorials/exchange-server-2010/compliance-pol icies-archiving/exchange-2010-client-throttling-policies.html

I've tried to post my email address a bunch of times now but Apple seems to be removing it. Not sure why, but I assume they don't want anyone on here contacting me. John and a few others somehow got lucky in contacting me and I was able to help them.

I've followed this discussion for a while due to problems with Mail misbehaving with Exchange. I followed the advice and reconfigured with Mail to use the IMAP instead of the Exchange server at my University. Perhaps because it's a University, the instructions on how to configure this were online and somewhat easy to follow.

I am pleased to report this has apparently (a few hours) solved two problems - mail now arrives in a timely manner and mail actually leaves the outbox in a timely manner.

Thank you for an excellent suggestion.

p.s. for large attachments I use dropbox links, and bit.ly. or if you are a bit more cautious, use Hightail.

🙂

consider sending your attachments as dropbox (less secure) or hightail (more secure) links, instead of documents?

If a well functioning mail is mission critical for you, I would recommend that you used one hour to try to set up and testan alternative product, like outlook. The interface might not be so pleasant and the operation might require some more clicks but the function with the exchange servers are fast and makes it possible to continue with the structure you are used to. I hear many complain about the price tag, but if mails are critical then this will get it working. Personally, my mail is working for 6 days now, after I got help by Bradhs from this forum, but I more calm after knowing that in case I can just switch to an alternative app.

A simple e-mail programme should be working without any problems!

davidmarc, Dropbox is also my way of getting around this for now - but realy a not satisfactory! Apple needs to wake up - and fix this. Googling the problem I have seen a LOT of notes about problems with Mail and Exchange, yet Apple-support seemed to hear this for the very first time. I run a business with many large file transfers and therefore depending on my e-mail to be able to send large files. I am really frustrated about this issue, since I cannot count on things running smoothly anymore. I have been talking to a very nice Apple support person for about two days - waisting time for both of us. Still not working. You should think support should know about this problem. I am very close to dump my new iMac and returning to my old Lion-version stone-age-mac. Or buy a pc instead.

- My mail on Maverick/ iMac wont send mails with attachments with exchange

- Failure notice says that exchange server is not responding, and I can choose another mail server to send from. Once I choose another (POP-)server to send from, my mail is sent, but no longer existing on my mac - not in sent-folder or anywhere else

- Calendar wont sync with my exchange - Iphone calendar works fine with exchange

- e-mails appear sometimes hours after they are sent to me

- My iPhone works fine and instantly, with both mail and calendar

- Apple Support made me unistall my anti-virus, still no effect

Hi Louise Graphics,

I feel your pain! I switched to Outlook for a while. Now trying IMAP to Exchange server and that seems (fingers crossed) to have solved the problem for at least 12 hours.

My provider limits my online account size, so I am allergic to large attachments. They clog my inbox. I much prefer links to large files.

I hope Mavericks 10.9.2 is the next messiah.

Louise Graphics,

The issues you are facing are more likely due to your Exchange server setup. Contcat your IT person and ask them to configure the Exchange server to support Mac Mail and Microsoft Outlook for Mac. Both Outlook for Mac and Mac Mail use EWS. Also, ask them to install the latest CU patches as there was a critical fix for Exchange that will contribute to solving the problem you are experiencing.

Mavericks 10.9.2 should fix Exchange connectivity for good. Also, you must make sure your Exchange servers are properly configured and patched. Without Exchange properly configured and patched you're going to be out luck, even with 10.9.2.

Bradley

Thanks bradhs,

I've sent your advice to my IT-(PC)-guys... Hope this will help... I'll let you know.

Hi there,

another email with a 119KB jpeg (screenshot) is stuck in my outbox again and blocking all my traffic...

Will receive my copy of office 2011 today. No changes will be made to the exchange server, it is a cluster and any changes will have to be planned very carefully, and that is understandable. I am not the CEO.

There are no reports of issues with outlook in the company, so that is my way to go. Pretty sure I will not go back to mail.

thanks

-chris

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 CU 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?