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can't send mail using exchange account in mavericks

Since upgrading to Mavericks I have had multiple problems sending mail. When I use my exchange account for work many emails will not send. This seems to happen more oftern when I have attachments, even reasonably sized attachments. The connection doctor shows a good connection to the exchange server. The messages just won't go out. I do not see any options in the settings for the exchange account that I can modify to fix this problem.

Posted on Nov 4, 2013 10:46 AM

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72 replies

Nov 8, 2013 3:24 PM in response to Daniel Mullin1

I started having the same problem.. surprisingly after today's update to Mail and iBooks apps. Mail won't send (it will sit in the "On My Mac" outbox for a couple of hours) and then I get a notification to "Try again with a different server". It seems that plaintext messages get sent perfectly.. but even if I attach a 250kB file, the message will not send, no matter what I do. Very frustrating.

Nov 12, 2013 9:09 AM in response to ken3448

Figure I will add my comments in here as well. Same type of issues as above. Using o365 exchange, after latest mail app update, now all exchange email with attachments seem to just sit my outbox.


If there is not attachment (or a meeting request invite), it seems to work more often than not. but I can't get into bug testing that deep. Attachments though, those always cause an issue.

Nov 19, 2013 3:35 AM in response to Daniel Mullin1

I also have this problem. Mails with attachment are (sometimes, not always) not send. After a few minutes, "select outgoing server" is shown and the mail is send. If I open the actiivity window in Mail Cmd Option 0, then is shows "Adding mail" (I do not know the exact message since I have a dutch version). But this never ends. It also helps to stop this process (hit the stop sign). Then stop and start mail and the message is send immediately.


I hope somebody finds a solution. at the moment Mail is useless since it sometimes does not send mail, which is a rather import feature of a mail programm

Nov 19, 2013 1:15 PM in response to Daniel Mullin1

I'm just adding myself to the list - exactly the same problem of sending emails, especially with attachments - 'select outgoing server' window comes up most times. Today an email with two pdf attachments sent on the second attempt but the attachments were empty files. When sending screenshots to my IT support service the screenshots were stripped from the email.


Also, whilst writing emails I twice received a message that said 'some actions taken while the account exchange was offline could not be completed online' - followed by a longer message. Net result was that the message I was working on was found in my recovered messages folder - but the window stayed open. I've never seen this before today - using same account on the same netork connection.


I hope we'll see a fix soon.

Nov 20, 2013 12:58 PM in response to Daniel Mullin1

I have the same problem too.

Even small, 50Kb attachments come back with the error message from the exchange server.

They usually go out after pretending to edit it, and trying to send it again the second time.



Mine is a Macbook Air with mavericks.

My colleague with a Macbook Pro and with mavericks does not have any problem sending attachments.

I also do not have problem sending attachents through gmail account.


Also my mail searches cannot find some of the emails.

Very frustrating.

One problem after the other (Wifi, Mail reindexing, Mail searches, attachments).

Nov 22, 2013 12:01 PM in response to Daniel Mullin1

Hi all,

With the internal server, external server, user name and password all defined, I disabled both 'use auto discover service' and 'use only this server'. When I open a new mail it gives me a choice though the correct exchange server is always the default - I am running two exchange services and two POP accounts, plus gmail.


Since then, I have had no problems sending although it still seems slower than I remember - and receiving is still much slower than my iPhone or iPad.


I hope that helps some of you.


Cheers

can't send mail using exchange account in mavericks

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