On Fri, Jun 11, 2021 at 10:32:38AM -0500, Linda Pagillo wrote:

> Thank you Herbert! I will give that a try. However... I'm trying to test
> connecting to port 465 over SSL from my Outlook mail client and it will not
> connect. Any ideas why not? I can connect to 993 and 995 from Outlook.

Test one thing at a time.  First get it working for interactive
connections via:

    $ (sleep 2; printf "QUIT\r\n") | openssl s_client -noservername -brief 
-connect 127.0.0.1:465

from which I see output of the form:

    CONNECTION ESTABLISHED
    Protocol version: TLSv1.3
    Ciphersuite: TLS_AES_256_GCM_SHA384
    Peer certificate: CN = amnesiac.local
    Hash used: SHA256
    Signature type: RSA-PSS
    Verification: OK
    Server Temp Key: X25519, 253 bits
    220 amnesiac.local ESMTP Postfix
    DONE

showing a working TLS handshake.  Once that works, proceeed to testing
Outlook, and looking at the Postfix logs for relevant diagnostic
messages.  It some mail clients' SMTP configuration, IIRC "SSL" refers to
port 465 implicit SSL, and "TLS" refers to port 587 "STARTTLS", make
sure you're configuring the client to use implicit TLS.

The Postfix source distribution includes a stock master.cf file, which
has a commented out sample "submissions" (port 465) entry:

    #submissions     inet  n       -       n       -       -       smtpd
    #  -o syslog_name=postfix/submissions
    #  -o smtpd_tls_wrappermode=yes
    #  -o smtpd_sasl_auth_enable=yes
    #  -o smtpd_reject_unlisted_recipient=no
    #     Instead of specifying complex smtpd_<xxx>_restrictions here,
    #     specify "smtpd_<xxx>_restrictions=$mua_<xxx>_restrictions"
    #     here, and specify mua_<xxx>_restrictions in main.cf (where
    #     "<xxx>" is "client", "helo", "sender", "relay", or "recipient").
    #  -o smtpd_client_restrictions=
    #  -o smtpd_helo_restrictions=
    #  -o smtpd_sender_restrictions=
    #  -o smtpd_relay_restrictions=
    #  -o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
    #  -o milter_macro_daemon_name=ORIGINATING

You should start with:

    465     inet  n       -       n       -       -       smtpd
      -o syslog_name=postfix/submissions
      -o smtpd_tls_wrappermode=yes
      -o smtpd_sasl_auth_enable=yes
      -o smtpd_reject_unlisted_recipient=no
      -o smtpd_client_restrictions=
      -o smtpd_helo_restrictions=
      -o smtpd_sender_restrictions=
      -o smtpd_relay_restrictions=
      -o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
      -o milter_macro_daemon_name=ORIGINATING

and change as little as possible to meet your needs.  If you end up
needing more complex rules, heed the advice in:

    Instead of specifying complex smtpd_<xxx>_restrictions here,
    specify "smtpd_<xxx>_restrictions=$mua_<xxx>_restrictions"
    here, and specify mua_<xxx>_restrictions in main.cf (where
    "<xxx>" is "client", "helo", "sender", "relay", or "recipient").

-- 
    Viktor.

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