I am using WinZip-19.5 on a Win 10 Pro machine. It has built in configurations for different email site; Outlook, Gmail, Yahoo. You can also configure your own server.
I configured it to use Postfix on my FreeBSD-10.1 machine. It fails. This is from the Postfix logs: Sep 13 11:22:41 scorpio postfix/submission/smtpd[18955]: connect from cpe-174-109-28-112.nc.res.rr.com[174.109.28.112] Sep 13 11:22:41 scorpio postfix/submission/smtpd[18955]: SSL_accept error from cpe-174-109-28-112.nc.res.rr.com[174.109.28.112]: -1 Sep 13 11:22:41 scorpio postfix/submission/smtpd[18955]: warning: TLS library problem: error:1408A0C1:SSL routines:ssl3_get_client_hello:no shared cipher:s3_srvr.c:1413: Sep 13 11:22:41 scorpio postfix/submission/smtpd[18955]: lost connection after STARTTLS from cpe-174-109-28-112.nc.res.rr.com[174.109.28.112] Sep 13 11:22:41 scorpio postfix/submission/smtpd[18955]: disconnect from cpe-174-109-28-112.nc.res.rr.com[174.109.28.112] starttls=0/1 commands=0/1 The connection, using TLS and port 587 works fine if I connect to Gmail, using a different account name and password obviously. I am running Posfix 3.0.2 -- Jerry