Exchange - inbound email only works from some servers

Posted by Kryptonite on Server Fault See other posts from Server Fault or by Kryptonite
Published on 2012-09-05T18:26:53Z Indexed on 2012/09/05 21:40 UTC
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I am having a problem where inbound mail from outside only works when sent from certain hosts.

For example, when I send myself an email from my personal gmail account all is well, as the logs show:

2012-09-05 18:14:16 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 EHLO 250 - -

2012-09-05 18:14:16 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 STARTTLS 220 - -

2012-09-05 18:14:16 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 STARTTLS 220 - -

2012-09-05 18:14:16 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 EHLO 250 - -

2012-09-05 18:14:16 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 MAIL 250 - -

2012-09-05 18:14:16 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 RCPT 250 - -

2012-09-05 18:14:48 209.85.223.175 mail-ie0-f175.google.com SMTPSVC1 MAILSVR 192.168.1.79 0 QUIT 240 - -

However, if I sent from my personal Yahoo account, I get this response:

Sorry, we were unable to deliver your message to the following address.
<[email protected]>: Remote host said: 530 5.7.0 Must issue a
STARTTLS command first [MAIL_FROM]

(NB: Nothing appeared in the smtp log for this message.)

Any suggestions where to start looking?

EDIT ----

I don't know if it matters, but the certificate I am using for TLS is self signed.

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