Exchange servers and Mavericks Mail

So I made a discovery, I think. The outgoing mail is being stored "On My Mac" not in the outbox for the Exchange account. When I looked at the account details under Preferences, the outgoing server read "none". So I selected the Exchange outgoing mail server from the SMTP list, saved that change, and then the email was sent. For some reason, when I quit Mail and relaunch, it goes back to reading "none" for the outgoing server. So this is what I think the glitch is. I don't understand why this happens.

Thanks to Apple Support, I found the answer to this, I think. Go to Keychain in Utilities and in the search box type the name of your outgoing server. If it's like mine a number of items will pop up. Delete all of them. Then go back to Mail and set up your outgoing server designation and save. Everything should now be fine. Fingers crossed.

Nice, but this problem has nothing to do with what everyone else is experiencing. Others here have documented a very specific BUG that really is not related to ssl certificates and/or saved passwords.

I see. I think.

Yes 10.9.1 seems to have changed the problem from "Faulty Exchange Sync" to "No email with attachments".

Where is Apple writing its SW these days? Have moved to Outlook!!

Actually Mail 7.1 still has got "Faulty Exchange Sync" - its just exacerbated by having an attachment. :-(

Thanks @johnfx!

I had a sh*tload of them in Keychain and deleted all of them. Got rid of the Certificates as well.
When I started mail again, somehow the outgoing Server was automatically added again in preference, so that was a bit weird. Might need to delete more than just the ones I saw in Keychain

Fingers crossed...

For what it's worth - I was having the same problem with sending attachments on Exchange. I'm sure this is not the solution but I change the "If outgoing server is unavailable" setting under preferences to "Automatically try sending later" and i am now able to send emails with attachments, 6mb attachments even. Something I could not do since the Mavericks release.

PROMISED TO KEEP EVERYONE APRISED. I received a response back from Apple in regards to where they are with using my test email account I created for them on my system.

"Hello Randy,

As of 12.17.2013 this information was pushed up to Apple Engineering as it was being looked at by Engineering at my current level. So it's moved to the higher Engineering level as of 12.17.2013.

I checked the ticket today, as of 12.18.2013 no current update. I will continue to monitor the ticket."

It appears they are working on the issue. The test account that I created for Apple on my Exchange server is exhibiting the same issues so that is good for purposes of reproducing the error in their labs. I had to popuplate a mailbox with about 20GB of data to get an Apples to Apples (no pun intended) comparison of the issues I"m encountering.

Randy

I'm trying the keychain idea described by Johnfx. This is a very frustraiting issue.

Yeah it is. There are so many dumb little problems with Mail now. One is that every email I send includes me as a CC. It doesn't matter whether I check or uncheck the box in Preferences. I still have the issue with emails with attachments, alhough deleting all the old mail server keychain items helped a bit. But it still asks me which server to use for outgoing. Another thing is that the popup shows the mail server I designated, but if you go to edit SMTP list it's not listed! What a mess!

As I said yesterday, Entourage is starting to look better to me, although syncing with my iPhone is a nice feature. Hey, one thought, is everyone who is having problems also using iCloud? I noticed a couple of weird sync issues with iCloud. Hmmm.

Tried the Keychain thing... No success. Will switch to AirMail, don't want to, but this is not working...

Installed the 10.9.2 update and here is what i've found

New Messages still beat the desktop to being delivered on my iPhone/iPad

I set the manual fetch option in Mail>Preferences to 1 minute and mail comes through in that time from my exchange accounts.

Not as fast as ActiveSync on iOS but it looks better. I'll continue monitoring this because my team has been waiting for this to be resolved too.

Anybody any luck with 10.9.2 and the issue with bouncing emails that include an attachment? I talked to Apple Support today and somebody at a senior level will call me back on Monday to see what is causing the issue.

Following upgrading to Mavericks I couldn't get mail to send attachments using my exchange account unless they were very small, they just got stuck in the "On My Mac" outbox. Having read this link: https://discussions.apple.com/thread/5475911?answerId=23821417022#23821417022 I tried changing my User name (in Preferences > Accounts) from simply "user.name", to "domain\user.name" and it seems to have fixed the problem, emails with attachments still appear in the "On My Mac" outbox rather than the "Exchange" one, but they get sent just fine. Hopefully the fix will persist.