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

Tried this and it does not work for me, unless I choose another (gmail) server, that I obviously don't want to do.

Same for me, but if I remove my pop accounts exchange seems to work be fine. Not a solution but maybe a clue??

Removing all accounts (POP and IMAP) except the Exchange account works for me!  Very strange behavior.

Won't work for long, see:

https://discussions.apple.com/thread/5470507

Relatively annoying. I am having the same issue. Searched, and can't seem to find a solution. Whenever I send with attachments the whole thing just stops. When presented with the choose another server option, and click try again, it works 75% of the time. Autodiscovery also is a mess.

Just sitting around trying to figure out a solution to my main email problem, sending emails without a lot of work-arounds. I was frustrated to the point of thinking of getting out my old PC but decided to start over again.

My solution was to delete all email contacts from Contacts.app (first made a copy). Going down to nothing left in the database, I reconnected with iCloud and selected (have everything else de-selected from that service). Now have Contacts (only). iCloud re-populated my contacts. When I went to an email I composed a test and used a group contact list. It went immediately when sent, too. It populated the email addresses in the BCC line with ease! Before this start over move, I had major problems getting those addresses to populate.

Looks like starting afresh was the key to my Macbook Pro computer so I'll try it with the iMac.

So I did find one thing that appears to work. My Exchange uses SSL. I only had SSL for internal selected. I have since checked it for External also, and so far so good I am working.

I have had all the same problems and none of the things suggested have worked.  I have just provided my feedback to Apple: http://www.apple.com/feedback/

You should do the same.

Same here... Just got of a chat with Support and they walked me through some settings and told me that it should work. Told him that we really didn't change a thing, but was willing to give it a try. Just tried it again and tada... email with attachment using Exchange... bounced back. What happens to me is that if I press "Try again" the receipients actually get the same mail twice so even though it bounces, it still sends the email.

How embarrassing is that.. Just discovered that same behavior—message gets sent twice. Makes it look like I don't know how to use email. I hope that a fix is in the works.

Deleting and then re-adding my exchange account in the "Internet Accounts" preference pane seems to have worked for me.

Though, it might be advisable to add the account as a duplicate first, before deleting it. I guess that way you don't run the risk of losing functionality you already have.

cheers,

Luke

I cannot send emails to multiple recipients nor emails with attachments.

Our entire IT department cannot solve the problem either..

Just adding my name to the list. Other work colleagues are having the problem. Given the length of this thread, might be nice for someone from Apple to assist. It is seriously affecting my productivity. I had no problems before donwloading Mavericks so very annoying.

Also noticed that PDFs can lock for short periods when scrolling post Mavericks.

I don't have a solution...but I can add some new info.

I am having trouble sending via Mac Mail using Mavericks on 2 computers from my home network.  Both computers are up-to-date with software updates.  Both using the same email account.  1 is a MacBook Pro using wifi, the other an iMac using ethernet.

I am traveling this week, and I have been able to send attachments from my MacBook Pro when using airport and hotel wifi.

So I am wondering if the issue is with my home router and/or ISP.