Mail app will not send a new message with yahoo account.

When I try to send a message it says try again with selected server I say say it can try agin with selected server. Then the same message keeps on poping up.

Hello andylow,
The article linked below provides some useful troubleshooting steps that can help you isolate and correct the source of the issue.
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/kb/TS3276
Cheers,
Allen

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Hi we have a problem with the Intra-Organisation connector between out Dubai and London office.
If they send us a plain message it is delivered OK, however if there is any attachment most of the time the message sits in the queue and continually retries. On some occasions messages do get delivered.
The errors vary between Connection Timed Out, Connection Dropped and 10061, No connection could be made because the target machine actively refused it.
As Dubai have a dynamic IP address they route all of their external mail via London and that is all going through OK. All of the other sites can send and receive OK with attachments both internally and externally.
To me this looks like I have a problem with the Intra-Organisation SMTP Send Connector on the Dubai server but I cannot spot anything that might be causing this issue.
They have worked previously however another issue did involve removing the Dubai server from the domain and adding it back in. Since then we have had this problem.
I have checked message size limits on the Send connector (100Mb) and the Transport settings (100Mb). I have checked the message size limits on the Intra-Organisation SMTP Send Connector (unlimited) and even on the user's mailbox (unlimited).
Any idea where I should be looking next?
Many thanks, Eddie

Hi Ed,
I think you may have hit on the problem - this is all one org so having read up more on this it should not be using this.
I spotted that the server was using this connector when I was looking the message tracking for the server and started looking into what it does and how to control it.
I used the Set-TransportServer command to set protocol logging on this to verbose, it get entries in the SMTP send logs like this:
2014-09-18T14:51:52.154Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,0,,192.168.4.5:25,*,,attempting to connect
2014-09-18T14:51:52.300Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,1,192.168.5.1:52766,192.168.4.5:25,+,,
2014-09-18T14:51:52.423Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,2,192.168.5.1:52766,192.168.4.5:25,<,"220 <remote server FQDN> Microsoft ESMTP MAIL Service ready at Thu, 18 Sep 2014 15:51:51 +0100",
2014-09-18T14:51:52.443Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,3,192.168.5.1:52766,192.168.4.5:25,>,EHLO <local server FQDN>,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,4,192.168.5.1:52766,192.168.4.5:25,<,250-<remote server FQDN> Hello [192.168.5.1],
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,5,192.168.5.1:52766,192.168.4.5:25,<,250-SIZE,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,6,192.168.5.1:52766,192.168.4.5:25,<,250-PIPELINING,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,7,192.168.5.1:52766,192.168.4.5:25,<,250-DSN,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,8,192.168.5.1:52766,192.168.4.5:25,<,250-ENHANCEDSTATUSCODES,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,9,192.168.5.1:52766,192.168.4.5:25,<,250-STARTTLS,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,10,192.168.5.1:52766,192.168.4.5:25,<,250-X-ANONYMOUSTLS,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,11,192.168.5.1:52766,192.168.4.5:25,<,250-AUTH NTLM,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,12,192.168.5.1:52766,192.168.4.5:25,<,250-X-EXPS GSSAPI NTLM,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,13,192.168.5.1:52766,192.168.4.5:25,<,250-8BITMIME,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,14,192.168.5.1:52766,192.168.4.5:25,<,250-BINARYMIME,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,15,192.168.5.1:52766,192.168.4.5:25,<,250-CHUNKING,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,16,192.168.5.1:52766,192.168.4.5:25,<,250-XEXCH50,
2014-09-18T14:51:52.576Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,17,192.168.5.1:52766,192.168.4.5:25,<,250 XRDST,
2014-09-18T14:51:52.591Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,18,192.168.5.1:52766,192.168.4.5:25,>,X-ANONYMOUSTLS,
2014-09-18T14:51:52.723Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,19,192.168.5.1:52766,192.168.4.5:25,<,220 2.0.0 SMTP server ready,
2014-09-18T14:51:53.072Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,20,192.168.5.1:52766,192.168.4.5:25,*,,Received certificate
2014-09-18T14:51:53.072Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,21,192.168.5.1:52766,192.168.4.5:25,*,FC006F5961FE665AD4FC1C0123FCEB6C0A477A49,Certificate thumbprint
2014-09-18T14:51:53.074Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,22,192.168.5.1:52766,192.168.4.5:25,>,EHLO <local server FQDN>,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,23,192.168.5.1:52766,192.168.4.5:25,<,250-<remote server FQDN> Hello [192.168.5.1],
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,24,192.168.5.1:52766,192.168.4.5:25,<,250-SIZE,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,25,192.168.5.1:52766,192.168.4.5:25,<,250-PIPELINING,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,26,192.168.5.1:52766,192.168.4.5:25,<,250-DSN,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,27,192.168.5.1:52766,192.168.4.5:25,<,250-ENHANCEDSTATUSCODES,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,28,192.168.5.1:52766,192.168.4.5:25,<,250-AUTH NTLM,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,29,192.168.5.1:52766,192.168.4.5:25,<,250-X-EXPS EXCHANGEAUTH GSSAPI NTLM,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,30,192.168.5.1:52766,192.168.4.5:25,<,250-X-EXCHANGEAUTH SHA256,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,31,192.168.5.1:52766,192.168.4.5:25,<,250-8BITMIME,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,32,192.168.5.1:52766,192.168.4.5:25,<,250-BINARYMIME,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,33,192.168.5.1:52766,192.168.4.5:25,<,250-CHUNKING,
2014-09-18T14:51:53.209Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,34,192.168.5.1:52766,192.168.4.5:25,<,250-XEXCH50,
2014-09-18T14:51:53.210Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,35,192.168.5.1:52766,192.168.4.5:25,<,250 XRDST,
2014-09-18T14:51:53.225Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,36,192.168.5.1:52766,192.168.4.5:25,>,X-EXPS EXCHANGEAUTH SHA256 ,
2014-09-18T14:51:53.225Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,37,192.168.5.1:52766,192.168.4.5:25,>,<Binary Data>,
2014-09-18T14:51:54.132Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,38,192.168.5.1:52766,192.168.4.5:25,<,235 <authentication information>,
2014-09-18T14:51:54.143Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,39,192.168.5.1:52766,192.168.4.5:25,*,SMTPSendEXCH50 SendRoutingHeaders SendForestHeaders SendOrganizationHeaders,Set Session Permissions
2014-09-18T14:51:54.163Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,40,192.168.5.1:52766,192.168.4.5:25,*,3757,sending message
2014-09-18T14:51:54.164Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,41,192.168.5.1:52766,192.168.4.5:25,>,MAIL FROM:<[email protected]> SIZE=98854 BODY=BINARYMIME,
2014-09-18T14:51:54.169Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,42,192.168.5.1:52766,192.168.4.5:25,>,RCPT TO:<[email protected]>,
2014-09-18T14:51:54.298Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,43,192.168.5.1:52766,192.168.4.5:25,<,250 2.1.0 Sender OK,
2014-09-18T14:51:54.300Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,44,192.168.5.1:52766,192.168.4.5:25,<,250 2.1.5 Recipient OK,
2014-09-18T14:51:54.316Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,45,192.168.5.1:52766,192.168.4.5:25,>,BDAT 98856 LAST,
2014-09-18T15:05:12.690Z,Intra-Organization SMTP Send Connector,08D1A167376C6407,46,192.168.5.1:52766,192.168.4.5:25,<,250 2.6.0 <23B7E7C020C8304085B1502492A968D13F75EA450D@localserver>
Queued mail for delivery,
So it does appear for some reason that the local mail server thinks it needs to use the wrong connector even though both servers that are in the same domain. It is odd that it only seems to affect messages with attachments.
Can you give me any suggestions to try and find the root cause of this problem?
Many thanks, Eddie

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