can't send mail using exchange account in mavericks

I have identical problem. 5 IMAP accounts and 1 Exchange acount. Only on this EX account I have regularlly problems with attachements. 1 minute or 2 after, I receive the message to try again, and normally it goes.

It deppends also on the quality of the net, or the place you are at office, home, airport or hotel.

The problem is that I found today that the email is going out twice. More than one prson told me, I got your email twice.

I was 5y ago a PC/outlook user. I won't give up of Mail, and I won't come back to any other version of OS. Just wait to Apple to solve the issues. It happens to every one.

Today I had an exchange email to send with a 6MB PDF attached. I couldn't wait at lunch time, and decided just to go away, expecting to find the "send again" up on my return. Surprise! No message, and the email was simply sent by himself.

So conclusion, be cool, seat back, or just continue working, and it will go. One day this will be solved. We all know the other millions of problems with PC's... We're just too stressed. Remember the time you had to go to the post office to send your letters... :-) Or asking the operator to make you an international phone call.

Just an update that changing the name did indeed fix the problem. Specifically, System Preferences --> Internet Accounts --> Exchange. The "Name" field needs to be in the "domain\username" format. I had assumed that this entry was for the reply-to name and had the username entered elsewhere in the email client account set-up.

Since I made this change, everything works perfectly--no more hang ups at all.

So I now regard this issue as resolved.

Did not work for me.

But changing it to just the username itself did!

change my name to my username and it fixed it for me

Thanks for your help

Changing my name to DOMAIN\Username WORKED!

Thank you internets!

DOMAIN\username does work, but only if I am under the domain (at the university).

It does not work from outside unless I try repeatedly.

I am experiencing similar issues with sending mail. Seems more when it comes to attachments. And I do not see this issue on my iPhone or iPad. Quite frustrating as I wish I never upgraded to Mavericks. I often wonder if all the Apple employees (almost 90,000) are using their own Apple Mail if they are experiencing the same issue. They must be pulling their own hair out on this one cause an issue like this seems widespread and it is not resolved yet. I run a software company (and my employees are reporting this same issue) and it seems every time we do a major release something goes awry. All the testing in the world (we think) and we still miss things. And I often wonder why don't we just leave well enough alone? Here is a fine example where I was perfectly happy with the previous version and like a dummy I hit the upgrade button cause it had newer and better features. I am sure they will get this eventually fixed but if there is another version called 11.0 I am not touching it for at least a year. Hopefully for all of us this next release that has been released to beta fixes this issue.

I apologize for not being able to post a solution

Well, in my mind i doubt that Apple are using Exchange for their servers!!

On another note, I have discovered that often when i get a message send failure, it ha actually gone, so I am constantly sending double mails on my work email account, very proffessional eh!!

Good point about Exchange and Apple. And I have seen the double send too. Thanks for the post.

I have a similar issue, but after the mail sits in the outbox and fails, it then asks me if it should try to send with the hosted exchange account. I allow it and the mail actually does go out. I hope they get this fixed soon. Microsoft BTW was of no help, they suggested trying use Outlook instead of Mac Mail - When I attempted that, I had a variety of sync issues. You guys may have noticed, but the issue only happens when there is an attachment in th email mail message...

I had the same issue. I thought it was my internet connection on Comcast, but I had upgraded it and still had the issue. The suggestion to do the following helped me:

Open Internet accournts in Control Panels

Select the Exchange acocunt

Click Details button

Specify <domain>\<username> in the Name field in that format

For example: apple\tcooke

Changing to Domain\username does not work for me. I'm over it. I'm ditching Mail when I have time to next week.

I hate to ask, because it is very likely that the answer will be removed, but is there a real alternative?

I'm not sure I understand the fix that has worked for some of you....

<domain>/<username>

In the Exchange / Email Account / Details I have my email address.

What do I place in front of it?

What will it affect?

What is the function of that email address?

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.