Mailing List Message #106013
From: James Roman <>
Subject: Re: being rejected redux
Date: Wed, 9 Mar 2016 10:55:40 -0500
To: CommuniGate Pro Discussions <>
X-Mailer: Apple Mail (2.3112)
One additional item to add. You can test the SSL authentication process manually using openssl by following instructions on this web site:

On Mar 9, 2016, at 10:03 AM, James Roman <> wrote:

I’m being a bit lazy by not looking up your previous post, but I can’t see from this message how is involved? 

I’ll focus on the logs provided for now. The session below looks normal for a test session. 

10:01:00.713 4 SMTPI-002041([]:46991) []:465
<- []:46991 incoming connection(

Connection initiated

10:01:00.845 4 SMTPI-002041([]:46991)
TLS-002539(ECDHE_AES128_SHA256) connection accepted for DOMAIN(

TLS session for successfully initiated

10:01:00.845 4 SMTPI-002041([]:46991) rsp: 220 ESMTP
CommuniGate Pro 6.1.9 is glad to see you!

Mail server sends encrypted response to begin ESMTP handshake

10:01:00.885 4 SMTPI-002041([]:46991) cmd: EHLO []

Client sends EHLO command 

10:01:00.885 4 SMTPI-002041([]) rsp: your
name is not []\r\n250-DSN\r\n250-SIZE\r\n250-AUTH LOGIN PLAIN

Server responds with available commands (2xx numbers mean that the server finds no problems so far.) 

10:01:00.922 4 SMTPI-002041([]) cmd: QUIT

Client quits session

10:01:00.922 4 SMTPI-002041([]) rsp: 221
CommuniGate Pro SMTP closing connection
10:01:00.922 4 SMTPI-002041([]) TLS connection is closing
10:01:00.922 4 SMTPI-002041([]) closing connection
10:01:00.922 4 SMTPI-002041([]) releasing stream

Session closed.

Typically instead of the QUIT command, the client would issue the requisite authentication command (AUTH LOGIN PLAIN CRAM-MD5 DIGEST-MD5
GSSAPI) instead. Since this is on port 465, authentication is required to send. If this is actually the apple mail client, either is is simply running the connection doctor to test the connection, there is no actual mail to send to this server, so it QUITs the session, or the client is balking at some aspect of the connection. If the client is balking, I would speculate that it may not like the certificate that the server is providing. There should be something in the Mac console logs that informs you. You may need to import the certificate into your Apple keychain and explicitly trust it. 

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