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Exchange 2003 dropping TLS connections.

Posted on 2012-04-10
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Last Modified: 2012-06-27
Hi Guys,

I've got a SBS2003 machine here that is having trouble with encrypted email. When the client sends the STARTTLS command Exchange replies with a 220, the client then sends the second EHLO, then the Exchange server drops the connection. I have tried this by connecting to exchange and typing the commands manually myself with putty and using ethereal to capture the mail stream of other mail servers connecting to our problem server. If exchange replied with a 550 I suspect the remote servers would fail back to un-encrypted, but since it's sending 220 ALL OK then dropping the connection, the remote servers don't fail back to unencrypted and we lose mail.

I've tried re-creating the self signed certificate using the sbs wizards with no success.

Full log below.

220 mail.problem-server.com.au Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at  Tue, 10 Apr 2012 16:55:26 +0930
EHLO sending-server.com.au
250-mail.problem-server.com.au Hello [203.xxx.xxx.39]
250-TURN
250-SIZE
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-TLS
250-STARTTLS
250-X-EXPS GSSAPI NTLM LOGIN
250-X-EXPS=LOGIN
250-AUTH GSSAPI NTLM LOGIN
250-AUTH=LOGIN
250-X-LINK2STATE
250-XEXCH50
250 OK
STARTTLS
220 2.0.0 SMTP server ready
EHLO mail.sending-server.com.au
<connection closed by remote host>
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Question by:nextsoln
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Accepted Solution

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nextsoln earned 0 total points
ID: 37830981
Exchange had been previously incorrectly configured to use a self signed cert for secure smtp. Removing the cert from exchange fixed the issue!
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