Exchange servers and Mavericks Mail

Did the people who manage your servers apply an update, do you know?

Evidently they (IT) are in the process of udating a 14 year old server from Exchange 2007 to 2010. They had moved everyone's accounts, except the two folks with Macs, my wife and her boss, when the issues started. They said they wanted to troubleshoot the update first before moving the accounts. I know little about Exchange server, but it seems understndable that these two accounts had problems if they had not been moved.

Things seem to be working okay. Although yesterday my wife was unable to send a couple of Exchange emails via Mail and had to resort to using TouchDown to do so. In the afternoon, her boss lost all conection to Exchange via Mail and also had to resort to using TouchDown. TouchDown has worked great for both of them but they prefer Mail so that they have one location for all their email accounts.

I heard that the TouchDown 3rd party add-on ActiveSync Email client was not ready for prime time. Is that not the case today?

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.

TouchDown is an application that support ActiveSync, if that is what you mean. Thus far I have been pleased but am just using it when Mail will not access the Exchange server.

That's grat to hear JohnnyDeLuxe! It appears you are running Exchange 2007, if you do not mind please do one of the following on the Exchange server so we can get an idea of which CU (Cummulative Update) is currently installed.

Option 1) To view the server properties in the Exchange Management console, follow these steps:

1. Start the Microsoft Exchange Management console.
2. In the navigation pane, expand the Server Configuration objects until you locate the server object, and then select the server object.
3. On the right side, notice the Exchange version number.

Option 2) To view the server properties in the Exchange Management shell, follow these steps:

1. Start the Microsoft Exchange Management shell.
2. Run the following command at the command line:

   get-exchangeserver

This further bolsters my stats which suggest this to be an issue isolated to those who are running Exchange 2010.

Hi bradhs,

I'm not familiar or have acess to Windows products, so can your suggestion be done from a Mac, and if so, where do I start? My search comes up with only windows like suggestions.

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.

Exactly my experience. Exchange is fine on iOS Mail. Airmail works without a flaw. OS X Mail in Mavericks fails intermittently and constantly need to be reinstalled. This is an Apple failure.

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.