Exchange servers and Mavericks Mail

Foil man, if the crappy MS product you talk about is Office for Mac with Outlook it was the only solution that worked. Just as well for 200 quid.

The windoze geeks in the building's IT department insisted Exchange was all fine. It is no fun being the only Mac user in such circumstances. No help from anywhere and trying to run a business. "Let down by Apple" is the only feeling you have.

Even if it gets fixed who in those circumstances would ever go back to mail. It takes days to resync years of mail history. Outlook works for us. Mail does not

It's not as simple as you make it sound

I use Exchange 2010, Mac Mail, Calendar and Contacts, everything works correctly (including delegation) In addition I have Outlook 2011 which also works but not as well as the Apple apps, and delegation does not work at all..

The cause of it not working for some (even for some who use Outlook) is yet to be found

Good:

Fortunately what worked for me did not cost 200 quid, didn't cost anything at all.

but

I'm looking for a reason why what fixed it for you fails for others, but as you're fixed you don't need to be a part of it unless you choose to.

Does delegation work for you in Outlook using Exchange?

Never tried delegation, no admin or partner to delegate to. Just needs to send and receive mail.

i joined this thread when we had the problem, came back when people asked for workarounds and when people jumped on the thread with new symptoms. I am out now.

Hi peter-watt, just reporting back after 4 days,

My mail with MAIL and Exchange are still working perfect, after setting the mail server adress manually and from within MAIL, not using the auto-discover function, thanks to the help of bradhs.

My problem with Mavericks and mac mail has to do with attachements getting stuck in the outbox...

I've now tried several different domains that I own on 2 different exchange providers (each hosted exchange provider uses Exchange 2010, which from my conversation with Apple is definietly supposed to work with mac mail (Rackspace being one hosted exchange provider that I've tried). I've also tried all of the other suggestions that users have posted and still no solution to most of my emails with attachments getting stuck in the outbox.

My echange email works with no problem on Outlook 2011 (which has other issues, so I prefer not to use Outlook 2011), so this is definitely a mac mail issue and Apple still has no clue to how to fix this. I've must have spent hours already on this issue and I am now very disappointed with Apple. I'll keep monitoring the forums, but an all-around fix will probably have to come from an Apple update to the mac mail app.

Any other work-around suggesitons would be helpful...

Hi agl74, I can help you fix that problem.

Your problem is most likely due to the Exchange server not be configured to properly handle a lot of EWS traffic.

Exchange has many methods of communications, RPC, RPC/HTTPS, EWS, OWA, IMAP, POP3, SMTP, etc. Mac Mail and Outlook for Mac use EWS. EWS was supposed to replace RPC/HTTPS but Microsoft hasn't done a great job with optimizing it yet. So, instead of optimizing the code, they went backwards and created a "Thottling" policy to effectively stop Mac Mail and other apps that use EWS from overloading the Exchange server with too many requests.

If you can't email me, here's basically what you need to do on the Exchange server. I'm pretty sure this will solve you problems.

1) Disable EWS Throttling

2) Adjust the MaxAllowedContnetLength on the EWS server

3) Adjust the MacRequestLength on the EWS server

4) Adjust the executionTimeout on the EWS server

5) Change the Connectin Timeout of the IIS server

I've helped a few people on here so far. Though, keep in mind that Mail is still broken in 10.9.1 and Apple is actively working on a fix. How "broken" depends on what version of Exchange and how your Exchange server is configured.

<Email Edited By Host>

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.

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.

🙂

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

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