Q: can't send mail using exchange account in mavericks

Hello,

I have seen the same thing on both of my MBPs with Mavericks.

What I did to *cause* the issue was to uncheck the, "Store draft messages on the server," box in Mailbox Behaviors.  I must have reckoned that keeping drafts on the server was simply a waste of time - why not leave them on my Mac until I was ready to send, right?  Wrong.

When messages (whether they had attachments or were just a little more wordy than normal) tried to move from the Outbox (On My Mac) to the server's Outbox, they'd hang.  Quick, "test 123," messages would go, but not meaty messages.

What I did to resolve the issue was to put the check back for Store draft messages on the server.

I'm sure somewhere in one of the logs will be a message telling me about the problem, I just haven't had a chance to look.

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...

This seems to be enough for me to get it work:

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

Sorry to poor cold water on this one. I have had the 'store draft messages box' ticked and no change at all. I still don;t get why this is a problem and hasn;t been subject to some sort of input/upgrade from Apple. It looks to me like I will have to dump Mail which is a complete pain in the ***.

ag174,

for 1, did you do <domain>/<username> or <domain>\<username>?

I did <domain>\<username> and it worked better for me but after a couple of days I had the issue again.  Odd though, it was not as bad as it was previously.

I just tried the #2 suggestion "Check the box to store draft messages on the server".  I have no idea why this would make a difference but it does seem to work better for me.

it should be a backslash so \

<domain>\<username>

@malcolm - I as well already had it checked.  It seems it is with just attachements.

Same problem here. Anythign with a message attached is bad news. I have four email accounts:  ICloud, an exdhange account and two POPs.

I originally had this aggravating problem but after changing a few of the recommended fixes I soon went back to what I had originally, then loaded Software  OS X 10.9.2 (13C64). I don't have any problems with either my iMac or MacBook Pro. Both are using the latest Mavericks update. Sometime back I changed my email settings to all using IMAP. I use iCloud for contacts and calandar and "Find My Mac" only. Whatever happened I am happy to have excellent service with email again (heavy professional user). 

Let me repeat what solved my problem: no funky domain name, no IMAP, no nothing, just

check the box in the "Mailbox Behaviors" => Draft:  Store draft messages on the server

So I've had the exchange account issue for awhile for 5 different exchange account emails.  I recently had to re-install Mavericks and the issue litterally stopped immediately.

Purely speculation, but could this have been a glitch with the upgrade version of the software? Because after a clean install it has gone away.

I don't know enough about computers to even begin trying what some of you have suggested. Where do I go to find "Change Description to <domain>\username and "check box to store draft messages on server". I went to system preferences but did not find those options. I am so frustrated that I can't send a simple E-Mail with 3 pictures attached. I clicked the send icon (paper airplane) but did not hear the sound that usually goes with it. I checked my SENT and nothing was there to indicate it was gone. As I write this (2hours later), I suddenly hear the SENT sound and a message in the corner saying Mail Delivery failure. What is going on??