>openssl s_client -starttls smtp -crlf -connect localhost:465 Using STARTTLS to port 465 (which should be a native SSL-listener) is wrong - and should NOT work.
The webpage you refered to shows: $ openssl s_client -crlf -connect zcs723.EXAMPLE.com:465 to test port 465 Making port 465 a plain listener is possible in assp - yes - but most SMTP software assumes a SSL-listener at port 465 per default. Thomas Von: "James Brown via Assp-test" <assp-test@lists.sourceforge.net> An: "ASSP development mailing list" <assp-test@lists.sourceforge.net> Kopie: "James Brown" <jlbr...@bordo.com.au> Datum: 12.12.2018 07:42 Betreff: Re: [Assp-test] Submission with Postfix & ASSP On 11 Dec 2018, at 3:23 pm, James Brown via Assp-test < assp-test@lists.sourceforge.net> wrote: Thanks Daniel. I changed master.cf to: 10026 inet n - n - - smtpd -o smtpd_sasl_auth_enable=yes 126 inet n - n - - smtpd -o syslog_name=assptls -o smtpd_tls_wrappermode=yes -o smtpd_proxy_filter= -o myhostname=mail.bordo.com.au ASSP: listenPort2 is 465 smtpAuthServer is SSL:127.0.0.1:126 James. Update: After adding to: /usr/local/etc/dovecot/conf.d/10-master.conf : service stats { fifo_listener stats-mail { mode = 0666 } fifo_listener stats-user { mode = 0666 } unix_listener stats { mode = 0666 } } Appleās Mail.app was able to send through! Thunderbird still gives the strange question marks and fails: Dec-12-18 17:13:41 [Worker_1] Info: try to connect to server at 127.0.0.1:126 using SSL Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:692: socket not yet connected Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:694: socket connected Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:717: ssl handshake not started Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:753: not using SNI because hostname is unknown Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:806: set socket to non-blocking to enforce timeout=5 Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:819: call Net::SSLeay::connect Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:822: done Net::SSLeay::connect -> -1 Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:832: ssl handshake in progress Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:842: waiting for fd to become ready: SSL wants a read first Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:862: socket ready, retrying connect Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:819: call Net::SSLeay::connect Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:822: done Net::SSLeay::connect -> 1 Dec-12-18 17:13:41 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:877: ssl handshake done Dec-12-18 17:13:41 [Worker_1] Info: connected to server at 127.0.0.1:126 using SSL - TLSv1_2 , ECDHE-RSA-AES128-GCM-SHA256 Dec-12-18 17:13:41 [Worker_1] Connected: session:7FA1A0ABD938 127.0.0.1:61009 > 127.0.0.1:465 > 127.0.0.1:61010 > 127.0.0.1:126 , 28-29 Dec-12-18 17:13:41 [Worker_1] [SSL-out] 127.0.0.1 info: bad line-end sequence in '????????????+?????9??????;????EC??1?H2??'?z ?BH`???H???9??F(????R??B?'Y?}????????????+?/?????,?0?????/?5?[LF]??????????????[LF]???????????????????????#????????????3?k?i??? ??@?X???3???????6?Im???[CR]???S]?2.???A?a7????I??0?ue'??????f??M??'??|d???R?????/}??????fl?q???????????H?+? ??????????[CR]???????????????????????????-???????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????' from 127.0.0.1 was corrected to '????????????+?????9??????;????EC??1?H2??'?z ?BH`???H???9??F(????R??B?'Y?}????????????+?/?????,?0?????/?5?[CR][LF]??????????????[CR][LF]???????????????????????#????????????3?k?i??? ??@?X???3???????6?Im???[CR][LF]???S]?2.???A?a7????I??0?ue'??????f??M??'??|d???R?????/}??????fl?q???????????H?+? ??????????[CR][LF]???????????????????????????-???????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????' Dec-12-18 17:13:41 [Worker_1] [SSL-out] 127.0.0.1 warning: got an unexpected SSLv3/TLS handshake Client-Helo-Frame of version (03.01) from IP '127.0.0.1' at local IP '127.0.0.1' and Port '465' - this frame is ignored Dec-12-18 17:15:27 [Worker_1] [SSL-out] 127.0.0.1 info: no (more) data readable from 127.0.0.1 (connection closed by peer) Dec-12-18 17:15:27 [Worker_1] [SSL-out] 127.0.0.1 disconnected: session:7FA1A0ABD938 127.0.0.1 - command list was 'n/a' - used 2 SocketCalls - processing time 106 seconds Connecting using: openssl s_client -starttls smtp -crlf -connect localhost:465 (As per Simple Troubleshooting For SMTP Via Telnet And Openssl - Zimbra :: Tech Center ) worked fine, so I suppose it is just a bug of Thunderbird? 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