Mail Connection Doctor is lying

Have been having problems sending messages through a SMTP server, others are ok but this one;
The other servers I tried greets with EHLO, this one old fashioned HELO.
Obviously from the log below, the connection and handshaking completers, even the initial HELO is being sent.
But it just sends QUIT after receiving the 250 response (ok), and lies to me that it could not connect.
I tried this with unencrypted SMTP as well, the same problem.
(SMTP works on the iPad and iPhone with exactly the same settings to the same server)
This has been going on for a while now.
Doesn't Apple have enginners that werent born when the ancient, and simple, SMTP protocol was introduced.
Do you even test your software against Sendmail (8.14.5/8.14.4, or others)?
A junior software developer implements a SMTP cleint in a few days.
OS X 10.8.5, Mail 6.6 (1510)
Gosh.
Connection Doctor says;
INITIATING CONNECTION Sep 28 14:43:02.146  -- host:mail.server.com -- port:465 -- socket:0x0 -- thread:0x7fef443293a0
CONNECTED Sep 28 14:43:02.821 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:mail.server.com -- port:465 -- socket:0x7fef43e71fb0 -- thread:0x7fef443293a0
READ Sep 28 14:43:04.608 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:mail.server.com -- port:465 -- socket:0x7fef43e71fb0 -- thread:0x7fef443293a0
220 mail.server.com ESMTP Sendmail 8.14.5/8.14.4; Sat, 28 Sep 2013 14:43:03 +0200
WROTE Sep 28 14:43:04.660 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:mail.server.com -- port:465 -- socket:0x7fef43e71fb0 -- thread:0x7fef443293a0
HELO [client-ip]
READ Sep 28 14:43:04.738 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:mail.server.com -- port:465 -- socket:0x7fef43e71fb0 -- thread:0x7fef443293a0
250 mail.server.com Hello client-reverse-ns-lookup [client-ip], pleased to meet you
WROTE Sep 28 14:43:04.793 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:mail.server.com -- port:465 -- socket:0x7fef43e71fb0 -- thread:0x7fef443293a0
QUIT

Yes, it is obviously a connection check.
Mail makes the same SMTP prologue when sending, decides that the server isn't up after the successful handshake and marks it bad, refusing to use that server for outgoing messages.

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