Exchange servers and Mavericks Mail

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?

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.

Well, whenever was said, using latest Maverics with Exchange 2013 with latest SPs.

Gues what? Why i came here? yup. same problems. and it started right after upgrade to Maverics and didn't stop yet.

sad. very sad. please fix ASAP. people claiming here for 3 months that there is problem within Mail.app and you just trying encounter everybody that this is Exchange problem? DO NOT BELIEVE.

And last. in english my nick something like "Angry beaver". never thought it will be used in such agressive reaction, but i really getting mad if someone trying to make me silly on my mind.

I'd like to add to zloibubr's comment that I too have worked both with Exchange 2010 and 2013 and the same problems are happening in both versions.

It's also worth mentioning that I only upgraded my desktop to Mavericks and still use ML on my laptop. The problems only occur in Mavericks. This is a clear indicator that the problem is not in Exchange, but in the new Mail.

It seems that Apple is not taking the appropriate actions to solve the problem. Apple support usually escalate this problem to engeneering, but an objective answer as to acknowledging as a bug never came (at least to me).

My current option is to go back to ML (I refuse to use the word "downgrade" when comparing ML with Mavs), as some other bugs are also bothering me.

I'd like to add to the din of voices hoping that Apple will address this problem. I'm running Mavericks on a late 2013 MBPR and have my email hosted via Rackspace Exchange 2010. Since converting to Mavericks, Mail will stall and essentially lose it's connection to the server. I get the screen that offers to "Try Again With This Server" and clicking this seems to renew the connection and all is well for a while. This happens at least 10 times a day, so it is more than a little annoying. I've checked with Rackspace and they contend the problem is with Mail, not the server. I've asked several techs on Apple JV and they have no idea. But, interestingly, those same techs have all said that I SHOULD NOT consider switching to iCloud for my business email activity as it isn't yet reliable enough. I'm beginning to think those of us with this problem are going to have to give up on Mail and use Outlook instead. Not something I want to do, but if Apple isn't going to support Mavericks working on Exchange, I don't see an alternative.

I can confirm the issue, running OSX 10.9.1.

exchange 2013 **3 (latest release) in combination with mail app 7.1. (1827)

push does not work. fetch setting on 1 minute does work.

iphone/ipad push works great, new email on server, directly delivered on mobile.

I think because the implementation of mail app and iphone/ipad is different, the activesync device registers itself on the exchange server (for remote wipe of the account), there for the exchange server is allways aware of the mobile device.

iphone/ipad uses /activesync directory with a listner service.

The mail app, uses /EWS (exchange Web Services) what means it communicates stand alone to the exchange server. (like a pull mechanism. with a polling interval.

Outlook 2011 also uses ews, and the push functionality does not work also like your mobile communication. (delay is about 20 tot 30 sec.)

Outlook for windows uses a different technique (MAPI) and communicate with RPC over HTTPS and push is immediately. (uses a listner)

so, i think that or the EWS needs to be changed on the exchange server side to accomodate same principal as activesync (apple/android/windows phone devices)

or

mail app/outlook 2011 need to have a shorter pull interval automaticly configured....

i think microsoft and apple needs to work on this case to figure out the best way....

put your mac mail app client on 1 minute pull, that is the shortest work around.

regards,

Leon

please see this, ews is polling mechnisme based:

http://books.google.nl/books?id=EZwSAAAAQBAJ&pg=PT312&lpg=PT312&dq=exchange+2013 +ews+polling+interval&source=bl&ots=qul6Ay7xnx&sig=BtTPa0c8hufLe0q5Td8q2H02_Ug&h l=nl&sa=X&ei=o0vqUrHLEqOH4AS9oICIBg&ved=0CIEBEOgBMAc#v=onepage&q=exchange%202013 %20ews%20polling%20interval&f=false

see scenario 1; 2nd text block. ews is a pulling mechanism, so the client allways have to initiate the pulling...

hi bradhs, i see that you got more technical knowledge about exchange 🙂

about the ews vs rpc (like MAPI is a better understanding).

Mapi is as old as microsoft almost is, they used mapi in the time that exchange came out on the first versions. so mapi communication is figured out. EWS is introduced in 2007 with exchange 2007, so not new and not old.

the RPC communication was mainly based in the early years for internal (domain related) communication, rpc is still used all over microsoft to communicate, with file shares, domain controller sync, sql server communication, like rpc is all over the place and is the backbone of communication.

so what they did is only encapsulation of the rpc protocol in an https packet so they could travel it secure over internet.

lets turn it around, why did outlook 2008/2011/mac mail (all versions) not use a MAPI/rpc side communication?

(political issue, like giving your source code to a another company so the can build/understand i can create something?)

Ok ontopic, i think disabling of throttleing policy's in your environment is not the smartest thing to do, if you got big envirionment with a few honderd mailboxes or more, you can get in to big performance issues.

i m more intressted in how to tweak the policies so ews is working with the new mavericks mail? do you have to right settings? (with exchange shell commands?)

Just in case we feel alone on this issue (as if 32 pages of this thread wouldn't convince you), check out this article on the subject published 2 days ago:

Apple OSX Mavericks Mail App Problems: Fix Crashes, Can't Send Outgoing Emails, Exchange Servers, Inactive Accounts And More [HOW TO]

www.idesigntimes.com/articles/9490/20140128/apple-osx-mavericks-mail-app-problem s-fix-crashes-exchange.htm

Unbelieveable that the problem is so massive, yet Apple support seems to be silent on the issue...at least on this thread. Any chance you forum guru's can step in and shed some light?