Re: Mac Server 5.4 Mail Service TLS Error

2017-11-14 Thread avignonais
Ah, ok, so this involves our certificate instead of a postfix mis-configuration of some sort. Yes, our (only) certificate is self-signed, we don't s u b s c r i b e to any SSL Certificate service. On the Mac we can specify "Always trust" when the Mail client first asks about the self-signed ce

Re: Mac Server 5.4 Mail Service TLS Error

2017-11-14 Thread avignonais
Did you get my PCAP file that I uploaded (see reply above). I sent it as you asked... -- Sent from: http://postfix.1071664.n5.nabble.com/Postfix-Users-f2.html

Re: Mac Server 5.4 Mail Service TLS Error

2017-11-13 Thread avignonais
OK.. I'm far from proficient in this, but checking for instructions online I *think* I was able to capture a pcap file that should include the failed email attempt sent from one of our Windows 10 PCs specifying "Require SSL for outgoing email." I looked thru the pcap file using Mac Terminal but hav

Re: Mac Server 5.4 Mail Service TLS Error

2017-11-10 Thread avignonais
Understood. Not sure I'd be able to install the debugger or sniffer utilities you link to, but FWIW here's the entire relevant logfile captured by that Terminal command I mentioned in my earlier reply. It's everthing that was recorded pertaining to a failed test email sent from our Windows 10 PC, w

Re: Mac Server 5.4 Mail Service TLS Error

2017-11-10 Thread avignonais
Thanks! From what I think you're saying, it sounds like this wouldn't be particularly fixable, at least not by me, LOL. That's ok, we can still send mail from the Win 10 PC if we uncheck "Require SSL for outgoing." Awhile back, possibly with Mac Server 5.3 or maybe even earlier, mail logs stopped

Mac Server 5.4 Mail Service TLS Error

2017-11-10 Thread avignonais
Mac Mini, 10.13 High Sierra running Mac Server 5.4. From a Mac client, specifying "Use TLS/SSL" in SMTP settings works just fine when sending out mail. However, from Windows 10 Mail running on a PC in the same network, I cannot keep "Require SSL for outgoing email" checked in the Win10 Mail setting