Exchange servers and Mavericks Mail

Hi peter_w,

just want to confirm that my setup after the modfications of the mail server adress carried out by brads, is still working fine after one month.

The exchange server has also (10 days ago) been updated - and says somthing like this now:

This seems to have helped other Mac users here, they report faster connection ect.

Hi JohnnyDeLuxe,

You will most likely have to get your IT department to provide you the details. It's not a big deal, I was just curious. I'm glad Mail is still working for you. Have a great day!

Brad

Just another person with this problem - and it is incredibly annoying. I have submitted feedback to Apple.

The only solution that has worked for me is:

1. Delete the exchange account in Internet Accounts in System Preferences

2. Manually delete the Exchange folders in:

~/Library/Mail/V2/

Of interest, I have noticed that I sometimes have more than one set of Exchange folders in the V2 directory.

3. Establish an new Exchange Account in Internet Accounts in System Preferences

4. Before you open email on any other machines (I have a desktop and iPad Air), make sure you delete all the Exchange folders in the V2 directory.

This generally works for a few days - until I suddenly can no longer send Exchange emails with attachments. And so it goes . . .

Dear Apple:

What kind of a joke is this? When do you plan on fixing Mavericks Mail to work with Exchange? It has now been more than 3 months. What a waste of time, energy and productivity this has been. I cannot recommend that any business use a Mac anymore.

AGL

Take a step back: There are plenty of folks who use Mavericks Mail with Exchange and don't have issues. I am one of them.

First: can you send e-mail using Mail and Exchange - a simple, "hello world," message with no signature?

No? Do you have a connection to the Exchange server - is Connection Doctor showing you have a connection? Are you using domain\exchangeaccount to sign in with? Have you tried connecting with the server's IP address? Turned on/off SSL? Using the correct SSL ports for your server? Do the server's mail logs show your machine making the connection at all? Is the server behind a VPN? Is your server patched? Is it a newer version of Exchange?

Yes? Then Mail+Exchange works, but you're having a problem with larger messages.

Okay - if that's the case, make sure you have Drafts saved on the server checked in Mailbox Behaviors. I unchecked this and found that messages would just sit in Outbox (On My Mac) and would repeatedly fail to send with connection issues. But checking it made the messages flow again.

Fact: many of those on this and other similar discussions had no problems whatsoever with Exchange until the day they upgraded to Mavericks. Period.

If there was something that needed changing in Exchange it was Apple's responsibility to provide the appropriate instructions. They didn't then and haven't since.

And four months later the issues - primarily significantly delayed inbound email and problems with outbound email with attachments - are still not resolved and the beta release notes for 10.9.2 do not seem to indicate a fix though I am guardedly optimistic.

Complain all you want, it won't solve the problem and - here's another fact: OS X Mavericks Mail + Exchange works for many, many people.

Open the Console, clear the log, start Mail, make a message and paste a simple screen shot into it (which makes the message big enough to fail) or make a message with ~150k of text (no attachment). Whether or not there's an attachment does NOT matter. The message size is the issue. Then send the message to yourself.

Wait.

Watch the log.

You'll see 'EXCHANGE' errors appear when Mail tells you the connection failed. This is a timeout. The message file (.EML) isn't moving from the LOCAL OUTBOX to the EXCHANGE OUTBOX. This is very likely because Mailbox Behaviors is set to save Drafts locally, instead of on the server. Change that setting, re-start Mail, then try the exercise again.

I had the intermittent failures. I had the total inability to send any kind of large message. Once I made sure my account was using domain\username and Drafts were being saved to the server in Mailbox Behavior, Mail+Exchange became rock solid.

OR

Don't do anything except complain and blame software you didn't pay a dime for.

Drafts are saved on the server.

Do you really believe that Airmail, a 1.99 app, shOuld have a more robust Exchange implementation than Apple Mail on OSX?

I am glad Mail has worked for you. it has not for me. This is not the apple experience I expect (having used Apple hardware/software for 29 years).

If I wanted this experience, I would use Microsoft products.

Drafts saved locally is not the problem. And, the fact that 10.9.2 is PRIMARILY focused on fixing these mail problems suggests that this problem is real and pervasive. I appreciate the advice for a tone of moderation, but have to concur that this was a collosal and damaging failure on Apple's part. What is most frustrating is that this problem is and has been known for some time, but no moderator has stepped into this ridiculously long thread to stop the madness. Apple screwed up on mission-critical serviceability and that's that. I'm over it, but please learn something from this. When it is clear that you have a problem, just own up to it and tell me you're working on it and I will continue to sing your praises. But, to ignore it and stay silent while you are secretly working on the fix hurts everyone; mostly Apple. Worse yet, you leave us to dangle with this needless speculations. The last 34 pages of this never needed to happen. What a waste of everyone's time. Please have more respect for the fact that most of us are trying to be productive and really want Apple to succeed.

By taking the following actions, I FINALLY got Mail to work for me:

1. Change Description to <domain>\<username>

2. Check the box to store draft messages on the server

3. Quit Mail and restart

I had to do BOTH 1 and 2 above to get it to work. It has been sucessful so far (tested with a few different attachments that used to give me trouble). I will keep monitoring to see if anything changes in different work settings...

All sorts of workarounds have been suggested but for a business tool it is unacceptable.

The facts are simple.

. For a significant number it does NOT work any more, the emphasis on "any more" . Mavericks broke it for some business users.

. It took weeks for Apple to notice the problem.

. It has taken weeks more to fix and test a beta that we have to assume contains a fix, but testers are forbidden from posting, only hinting. No acknowledgement from Apple because it is too darned embarrassing.

. Mavericks is not free, the cost of Macs contains a significant premium to pay for Mavericks for all existing users . The rest is made up by savings by dropping outdated services like syncservices which will also in some cases lead to paid-for icloud storage. There is no need to feel guilty that we are ungrateful recipients of bounteous gifts.

I've been seeing problems with Mail + Exchange on 2 out of 3 machines all running latest version of Mavericks (actually 2 out of 4 machines if you include my laptop).

Something that seems to have worked on 1 machine where I have tried it is to create the mail account on the Mac as an IMAP account rather than an Exchange account.

Something else that I noticed while doing this is that there is some kind of authentication problem going on. The user's password was not accepted by Exchange when set up as an Exchange account but worked fine when set up as an IMAP account. Additionally, when I re-enabled the Exhchange account on the Mac it would no longer accept the password - which previously was working (or at least not indicating that it didn't work).

I need to research and test further but I have a feeling there is some issue with the way in which passwords are encrypted. In older versions of Mail it was possible to specify the encryption method for passwords being sent to the Exchange server (they would only work with this setting set to "Password"). This no longer seems to be the case and I could see no way to change the way passwords are sent. So I wonder if the fault is in the way the password is encrypted at the Mac end or decrypted at the Exchange end.

Due to the password "working" then not working once I disabled and tried to re-enable the Exchange account I also wonder if this is to do with upgrading the OS and the account being automatically migrated from Lion - where everything worked fine.

Like I said, I haven't had time to fully test this but the user who I applied this quick fix to told me this morning that he has not had any problems with Mail since I did it (a few days ago) where he was having multiple issues daily prior to the fix.

To be honest this issue with Mail and Exchange is a major problem and not something that Apple seems happy to ignore. I've had problem with my iphone, ipad and Mail on my macbook. I've got Outlook which works without fault. However I use Daylight which links to Mail. So its important for me that Mail works properly with Exchange. I'm a small business owner and really dont have time to spend hours looking for work arounds. Apple should be ashamed of themselves!!!!!! How can they expect to grow they business market if they cannot get the basic requirements of email right!!!!

Not exactly - I'm still seeing that a mailbox stops receiving new messages after a while.

This is being observed on newly configured machines and those with existing V2 data in the users library/mail folder.

Going to keep testing but definitely much better than anything available before.

BradHS, if there are specific instructions for setting up Exchange, why isn't Apple publishing them, since whatever the setup might be it is different to what worked for Mountain Lion and previous OS versions? All these issues started the minute I/we upgraded to Mavericks. Exchange setup wasn't touched.

I installed 10.9.2 and see no difference. Nor do the release notes suggest any as it relates to Exchange. Closest comment is: 'Resolves an issue that prevented Mail from receiving new messages from certain providers'. No mention of Exchange whatseover. 'Certain providers' is surely not a common way to describe Exchange. No mention of Exchange issue resolution in 10.9.1 or 2 release notes or pre-release notes either based on screen shots I have seen.

If Apple was simply trying to save on space in their release notes, there are nearly 89,000 views of this discussion alone on the subject, one of two dozen such discussions on this forum when I last counted, so it would suprise me that if they fixed the issue they would be so shy to mention it. Especially since it affects corporate users, some very large.

I have, personally, two iOS 7 devices and one OS X 10 connected to our Exchange Sever 2007 SP3.

The iOS devices are perfectly synchronous in every way: inbound email, outbound email, deleted email, etc. Always have been. So was Mail prior to Mavericks though our sys admin had to create workarounds to achieve this, evidently.

With Mail set to 'check for email automatically':

Inbound messages in OS X Mail are delayed in what appears to be a random fashion: anywhere from a minute or two to twenty minutes plus. Unless one closes and reopens Mail. The time stamp is always the same as for iOS, so presumably set by Exchange. So a message time stamped '2:40pm' actually arrives in Mail at 2:42pm or 2:55pm or whenever. Same in 10.9.2 as 10.9.1 and 10.9.

With Mail set to 'Check for email every minute':

Inbound messages arrive within a minute.

And if that was all, I could live with the problem until Apple finally gets around to fixing it.

But when you delete an email in Mail:

On iOS 7, it generally won't delete in OS X 10.9, for maybe 10-20 minutes, or won't at all, until you click on it, at which point it dissapears instantly.

On OS X 10.9 it might quickly delete in iOS 7, or after an extended period or not at all (i.e longer than I have tested). And if you try to manually delete in iOS it indicates 'Can't move to trash', or words to that effect.

I have been going through these functions all afternoon with a stopwatch. My head is aching, my eyes are blurry and I can't get beyond what seems like pretty random behavior.

I need to go back to running my company and our sys admin has little appetite for matters Apple at this point though they will do what they have to to keep their Apple loving CEO happy!