Exchange servers and Mavericks Mail

Spent a long time troubleshooting this issue with being unable to get Mail.app on Mavericks to sync an Exchange 2010 mailbox, I had tried a lot of steps in this thread already including removing the V2 folder from /Library/Mail and recreating accounts and such like but nothing worked.

What fixed it for me:

Open Mail.app>Preferences>Accounts

Highlight your Exchange account. Under the Account Information tab untick "Use Autodiscover Service"

Internal server address: use your OWA FQDN address such as mail.companyname.com

External server address: leave this blank

Click Advanced tab. Under the "External Server Path" - untick "Use SSL" so the external port defaults to 80

Leave the external and internal EWS paths as default on /EWS/Exchange.asmx

Click the General button at the top, and save changes

Do Mailbox>Get New Email

At that point all mail was sync'd at expected speed including subfolders etc

Hope that helps others.

Cheers

I see sent mail bounce from the exchange server as well, but managed to fix it by making sure the attachment contains only standard characters in the filename. Nonstandard characters in the filename might make it bounce from the exchange server.

Also removing nonstandrard characters (apostrophes, non-english characters, etc) from the "computer name" in System Preferences/Sharing may help.

I will also add, the post a little bit ago about having subfolders under the inbox seems to have helped me quite a bit. I used OWA to move all the subfolders under the Inbox to root of the mailbox, it still gets stuck sometimes but nowhere near as often...

Hope this is of value to most of you. I have been working with Apple tech's on this issue since day 1. After not getting anywhere I decided to write to Tim Cook and on Friday I received a call from a high ranking tech at apple who will be working with me to gather information. More specifically I am creating a test account for them on my exchange server and will be populating it with my soon to be exported PST file. This should provide them the informaion that they need. And to respond to the previous email about manually setting the Outlook Anywhere/AutoDiscover settings I used that approach early on and it did work for a few days but eventually the issue came back for me. I do believe the issue is related to Outlook Anywhere/AutoDiscover but I also believe there is one other issue that has to do with Mailbox Synch.

Randy

Bravo. Hope you get some good results.

While you are "in" you might want to ask why it is not possible to export Mavericks Mail stored locally on a Mac to anywhere else (e.g., to Outlook 2011) because Apple changed the properties of the exported mbox file so it is no longer readable. Why break things that are working fine.....

thx

Alan

randyKates wrote:

Hope this is of value to most of you. I have been working with Apple tech's on this issue since day 1. After not getting anywhere I decided to write to Tim Cook and on Friday I received a call from a high ranking tech at apple who will be working with me to gather information. More specifically I am creating a test account for them on my exchange server and will be populating it with my soon to be exported PST file. This should provide them the informaion that they need. And to respond to the previous email about manually setting the Outlook Anywhere/AutoDiscover settings I used that approach early on and it did work for a few days but eventually the issue came back for me. I do believe the issue is related to Outlook Anywhere/AutoDiscover but I also believe there is one other issue that has to do with Mailbox Synch.

Randy

Way to go, Randy, Let's hope you are one of many and they really were working on it before, but at least they are aware of it now. They can put out a patch any time - they did it with Gmail.

itsnotarace,

We tried your approach and it seems to work better for us so far. No fully but

Meanwhile, yesterday I finally launched Outlook, out of a desire for a workable short term solution (I much prefer Mail). It then announced an Office database error and this seems to have caused a problem with Mail synchronization with Exchange - a first ever such experience. Both are slowly re synchronizing.

randyKatyes,

Amazing to me that with 210 replies and nearly 26,000 views of this discussion and at least equal numbers in aggregate among the literally dozens of other discussions concerning the same issue on this forum, that Apple still seems surprised or at leasts feigns surprise that there is an issue.

Paul

This is the exact same issue I'm having, and it happens randomly. Does anyone know if the beta 10.9.1 and Mail 7.1 will resolve this issue? Hopefully someone is running it. If it has not, I'm going to keep searching for a solution.

TheTransplant wrote:

I have an odd issue with my OSX Mavericks Mail and Exchange setup. Everything is (mostly) working. However, every so often I send a message and it does not go out. Then about 3-4 minutes later I receive a prompt from mail that the message was unable to be sent using the Exchange server. I then offers me a list of SMTP servers to choose from with the Exchange server highlighted. I then select Try with selected server (which was the original server that I was sending through) and it works fine. This seems to happen more with emails with attachments - perhaps timeout issue?

theoretician,

About a month ago, after upgrading to Mavericks and experiencing the exact same problems described here I logged a bug about the problem (15473462) hoping that more bug reports would raise the visibility of the problem. However after providing logs and diagnostic information I did not get any updates until a couple of days ago when my bug was closed as duplicate of "15577831 (Open)". It seems all I can do at this point is see if the other issue is still open or not, so in the same situation as you.

Today they released an update for Mail. Before I installed Maverick, I was using Mail Mac version 7.0. That version was problem free. However, when I installed Maverick on the day it was launched (October 2013). I was experiencing numerous of problems with Mail with all my exchange emails. My Mail version after Mavericks update became 10.9.

People stated how they had issues with Gmail for syncing/receiving/sending emails. But I was experiencing the same issue for my exchange emails.

After today's update, strangely enought, my mail version from 10.9 and now became 7.0.

Mail Version (before update):

10.9

Mail Version (after update):

7.0(1822)

Not sure why if I am the only one experiencing the versions dropping after todays update. Let's hope this is the fix. Is anyone else experiencing the version change after today's update? If so, how are your exchange emails working?

Thanks

That update is from a while back. They must have just gotten around to applying it. It certainly didn't improve my Exchange issues. In fact they've gotten so bad that I've finally given up and am running Outlook from Office 2011 just for my Exchange account. It's maddening and really an embarrasement for Apple in my opinion that they still haven't gotten it right for the desktop after all these years. It works fine on iOS. Maybe they should get get some of the software guys from that team to step in anf figure out what the heck is going on.

I switched to Outlook.

Just beware that you will have difficulty moving any emails that you had stored on your computer using Mail. Mavericks altered the file attributes such that Outlook cannot read them. I am still trying to find a solution...

Alan

I switched to Microsoft Outlook 2011 and it seems like my emails are working fine. All the emails are syncing/receiving/sending by the looks of it.

I do prefer using Outlook rather than Mail though. For instance, you have 'Calendar' 'contacts' tasks' notes' all in one program rather than having them all in separate applications. The Calendar on the Outlook is more structured and easier for the eyes to read (or maybe its just me)

The only problem I have with the calendar is, all my 'categories/tags' that I created on outlook, DOES NOT show up on iCal. Unless there is a way? It would be a pain having to create all the categories and having to click on each individual post on the calendar to put them in the right category.

I do see my events/appts/meetings synced, but on iCal it just says 'Exchange' and the category would be 'Calendar'. And nothing that I created on outlook would appear under that list.

Hmm..

There was an update for Mavericks released today. If it does not show up in your normal software update, You can go to the app store and search 10.9.1. It will bring up the update and can be downloaded from there. I installed it and it does have a great deal to do with Mac Mail. It also "rebuilt" my inbox to "make it more efficient" I cannot yet confirm if it corrects the hangging emails with exchange but hope it does...

Thanks for the heads up. It does show in my App store. It has been downloaded and seems to be working with Exchange. You never know for sure untill a few hours have passed. Most times when the computer is restarted the mail from exchange will come in for awhile. I hope this is the exchange fix. Thank you Apple is it is!!