Tablo ripper ssl

I understand everything you have said
I see the problem as ripper forces ssl
and does not accept self signed certificates, or clear text email server
since I don’t want to register the domain I am out of luck with ripper app
maybe using a gmail account or some other registered domain with a valid MX record lookup.

from postfix log file
both configured the exact same, postfix relay server ip “192.168.12.10 server1” port 25
windows10 pc 192.168.12.65

ripper test ----------------------------------------------------------
Aug 13 14:02:10 server1 postfix/smtpd[4387]: connect from unknown[192.168.12.65]
Aug 13 14:02:10 server1 postfix/smtpd[4387]: lost connection after STARTTLS from unknown[192.168.12.65]
Aug 13 14:02:10 server1 postfix/smtpd[4387]: disconnect from unknown[192.168.12.65] ehlo=1 starttls=1 commands=2

wifi softperfect test------------------------------------------------
Aug 13 14:02:59 server1 postfix/smtpd[4387]: connect from unknown[192.168.12.65]
Aug 13 14:02:59 server1 postfix/smtpd[4387]: 2C2382C07A6: client=unknown[192.168.12.65]
Aug 13 14:02:59 server1 postfix/cleanup[4411]: 2C2382C07A6: message-id=<>
Aug 13 14:02:59 server1 postfix/qmgr[3409]: 2C2382C07A6: from=me@comcast.net, size=429, nrcpt=1 (queue active)
Aug 13 14:02:59 server1 postfix/smtpd[4387]: disconnect from unknown[192.168.12.65] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
Aug 13 14:03:02 server1 postfix/smtp[4412]: 2C2382C07A6: to=me@comcast.net, relay=smtp.comcast.net[68.87.20.6]:587, delay=3.5, delays=0.05/0.01/3/0.36, dsn=2.0.0, status=sent (250 2.0.0 6JRDkxen5YPV76JRGkTDhn mail accepted for delivery)
Aug 13 14:03:02 server1 postfix/qmgr[3409]: 2C2382C07A6: removed

======================================================

Have you tired importing the self-signed certificate from your mail server into the Trusted Root Certification Authorities store on windows computer? I suspect that would permit TabloRipper to trust the certificate

33+ years in IT and this is a bit over my head. The following came to mind (my apologies):

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