On Tue, May 12, 2020 at 03:08:16PM -0700, Alexander Vasarab wrote:

> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: > <data scrubbed>[<data 
> scrubbed>]: 250 2.1.0 Ok
> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: watchdog_pat: 
> 0x55bec82e41e0
> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: < <data scrubbed>[<data 
> scrubbed>]: RCPT TO:<<data scrubbed>>
> 
> ...lots of debug info e.g. config maps, etc...
> 
> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: > <data scrubbed>[<data 
> scrubbed>]: 250 2.1.5 Ok
> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: watchdog_pat: 
> 0x55bec82e41e0
> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: warning: TLS library 
> problem: error:140E0197:SSL routines:SSL_shutdown:shutdown while in 
> init:../ssl/ssl_lib.c:2086:
> May 12 14:27:22 vasaconsulting postfix/smtpd[3482]: smtp_get: EOF

That's really weird, your server is closing the connection for no
obvious reason, right after sending a "250 OK" for "RCPT", and with no
indication from the client at either the TLS or TCP layer that there's
no more data.

At this point, clone your submission service onto port 588, and
configure that copy with "smtpd -vvv" + all the other options.
Then use your client to connect to port 588, and there should
now be voluminous logging from the Postfix I/O layer (events
and vstreams).  The question is now whether Postfix is seeing
EOF from OpenSSL and then reciprocating by closing the stream,
or somehow deciding to close the stream (for no obvious reason).

-- 
    Viktor.

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