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

Same problem here, mail withour an attachment works fine, mail with attachment sometimes not.

I found a workaround: save the mail, force quit the mail program and start is again. Then I can send the mail with attachment.

Waiting for final solution from Apple.

I posted yesterday on this issue. I am not able to detect any pattern to it. Sometimes the dialogue box will pop up asking me  'to try with a selected server' other times not.

Sometimes outgoing messages are slow, sometimes instantaneous.

Sometimes mail appears to have problems with attachments. At the moment the message I am trying to send doesn't have an attachment.

This appears to be a serious problem and not something I have experienced before with updates. Is this Apple succumbing to falling standards by releasing a product that has not been properly tested?

I'm having this same problem with Mail on Mac OS 10.9 not sending outgoing emails (with or without attachements) to either gmail or exchange servers. I now have 15+ emails from the past few days just sitting in the Outbox! Nothing I've tried so far has had any effect.

Help us APPLE!

yet another update. This morning i can't send emails with pages documents converted to word, even though 'connection doctor' is saying that I am connected to my work exchange server. How many times do we all have to write that this fault is incredibly annoying and is seriously effecting our work before we get some response from Apple.?

I have the same issues - mail not working properly with exchange, more specifically when trying to send attachments. it sits in the outbox for a while and sometime's i'll get lucky and a window pops up where I can choose the smtp setver and then it sends it. other times that doesn't work and I h.ave to either restart mail or restart the computer I just upgraded today to mavericks 10.9.1, which was supposed to fix some email issues, but now it's even worse.  Now it doesn't necessarily send when I choose the smtp server (if the window pops up). i've spent hours trying to fix this problem. apple tech support doesn't seem to think it's a system wide issue and keeps telling me that perhaps my exchange settings aere incorrect when I know the settings happen to be 100% correct since I use the same email account on various devices and my mac with mavericks is the only one giving issues. APPLE: if you are reading this, please fix this. I made a switch recently from PC to Mac and I can't even use Outlook 2011 for Mac since it has too many of its owe issues. If this isn't fixed ASAP, I will need to return my Mac and revert back to a PC. It's not possible to work like this...

Hello people,

I have had the same problem since Mavericks came out, with intermittent message send failure, and on hitting retry it would go. Finally figured out what was causing it today, but why it was happening I don't know.

I finally twigged failure to connect would only happen on emails where I had a signature attached. The signature had two small PDF images in it. I tested this a couple of times and was definetly the signature causing it!

I have created a new signature, with exactly the same format and images, voila!! no more failures.

Do not know why it was failing, it has worked with the same sig for the last 2 years!

Anyway, if you have a signature attached normally, try without and if this works create a new signature!

Good luck!!

We should all move to this discussion... 16 pages...

https://discussions.apple.com/message/24153376?ac_cid=tw123456#24153376

still having the same problem since Day 1. Was hoping there was a fix for this by now.

I'm having these issues also. Just came over from Entourage and severely regretting it.

"disabled both 'use auto discover service' and 'use only this server'"

this worked for me, thanks!

Hello everyone,

The Mail.app problem with Exchange accounts appeared to me some time ago. In particular, I noticed that whenever I have attacments in my emails that I'm trying to send, everything stays in my Outbox.

My solution was the following: In "System Preferences -> Internet Accounts -> Details... -> Name " (maybe this is the same as in the settings in Mail.app) I changed my real name to the form

DOMAIN\username

I haven't had any problems (sending) after this adjusment and if I change my real name back in Details, the problems are coming back. Also some delays (in my mind) when receiving emails seems to be gone.

The part "disabled both 'use auto discover service' and 'use only this server'" didn't help me.

Try this and maybe it solves your Mail.app problems. I'm still a bit sceptical and waiting the problem return. We'll see...

I just tried it and--provisionally--it seems to work.  We shall see if it is a consistent fix.  Many thanks for the suggestion as it was just in time (I was syncing up my hated Outlook 2011 client).

I tried changing the name to DOMAIN\username and this didn't fix the issue.

I've now tried several different domains that I own on 2 different exchange providers (each hosted exchange provider uses Exchange 2010, which from my conversation with Apple is definietly supposed to work with mac mail (Rackspace being one hosted exchange provider that I've tried). I've also tried all of the other suggestions that users have posted and still no solution to most of my emails with attachments getting stuck in the outbox.

My echange email works with no problem on Outlook 2011 (which has other issues, so I prefer not to use Outlook 2011), so this is definitely a mac mail issue and Apple still has no clue to how to fix this. I've must have spent hours already on this issue and I am now very disappointed with Apple. I'll keep monitoring the forums, but an all around fix will probably have to come from an Apple update to the mac mail app.

Same here in relation to change of personal name. I have posted a few times about this issue. Why the deafening silence from Apple. This problem in mail affects my work considerably. I haven't had time to change from mail to a different mail program which is going to be another monumental pain in the ***. However, I can't see an alternative. Given that mac users were encouraged to change to Mavericks  I would have expected a little more support from the company. This have been a problem since Mavericks was released. Customer Service seems a low priority at Apple.

Perhaps the only viable solution for me in the meantime is to install Mountain Lion and get rid of Mavericks. I bought a late 2013 macbook pro, which is supposed to be optimized for Mavericks.

Anyone have any idea if I could purchase Mountain Lion online and if so, will it just overwrite Mavericks and I'd be good to go with mac mail? Any advice would be helpful.