>Otherwise, the absense of "AUTH" in the EHLO reply might be a configuration >issue with dovecot, or is rather mysterious.
Well, at least no AUTH was something to go on, thanks, I missed that detail. Checked the socket path setting and the file permissions, all looked good there. I Found what I hope is the main issue and cure. Since I was able to send a message to the server from an iPhone, I'm getting close. Noob error but its something I haven't set in a while, didn't realize it was there. An Outlook drop down for "Use the following type of encrypted connection: None, SSL, TLS, or Auto. It was set to none. Fixed. Now if I try to connect I get the AUTH But the message is rejected with recipient address restrictions: Jul 24 15:35:28 tn2 postfix/smtpd[10358]: >>> START Recipient address RESTRICTIONS <<< Jul 24 15:35:28 tn2 postfix/smtpd[10358]: generic_checks: name=reject_invalid_hostname Jul 24 15:35:28 tn2 postfix/smtpd[10358]: reject_invalid_hostname: HDPLEX2 Jul 24 15:35:28 tn2 postfix/smtpd[10358]: generic_checks: name=reject_invalid_hostname status=0 Jul 24 15:35:28 tn2 postfix/smtpd[10358]: generic_checks: name=reject_non_fqdn_hostname Jul 24 15:35:28 tn2 postfix/smtpd[10358]: reject_non_fqdn_hostname: HDPLEX2 Jul 24 15:35:28 tn2 postfix/smtpd[10358]: NOQUEUE: reject: RCPT from hh-hh-hh-hh.lightspeed.nsvltn.sbcglobal.net[hh.hh.hh.hh]: 504 5.5.2 <HDPLEX2>: Helo command rejected: need fully-qualified hostname; from=<shor...@tn2.myserver.com> to=<shor...@tn2.myserver.com> proto=ESMTP helo=<HDPLEX2> Jul 24 15:35:28 tn2 postfix/smtpd[10358]: generic_checks: name=reject_non_fqdn_hostname status=2 Jul 24 15:35:28 tn2 postfix/smtpd[10358]: >>> END Recipient address RESTRICTIONS <<< The client PC's "name" is HDPLEX2. Is there a (safe) workaround to this without changing all my Windows PC's to FQDN names?