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Trying TLS on mail.DOMAINNAME (5):Īs you can see it shows the new SIZE but the SmtpReceive logs again show it was sending STARTTLS:

To make sure I was talking to the expected receive connector I disabled the others and doubled my maximum message size. I checked the SmtpReceive logs (which I set to verbose for this test) and they showed it was sending STARTTLS (along with a bunch of other stuff): I was fixing an issue with Reverse DNS Mismatch (had the ISP change it) and noticed a "Warning - Does not support TLS." with the mxtoolbox SMTP test which I thought odd as it showed that we weren't advertising STARTTLS after receiving an EHLO:Ģ20 remote.DOMAINNAME Microsoft ESMTP MAIL Service ready at Thu, 09:42:10 -0700 Ģ50-remote.DOMAINNAME Hello If this is long, I tried everything I could think of. Email, OWA, Activesync all working fine, ESET mail security 4.5.

Exchange 2010 SP3ur8 on 2008R2 SP1 fully patched, single server, static IP address, default settings with self-signed SMTP certificate and Internet receive connector setup for TLS.