---

smtpd_tls_security_level: "none"

extra_mydestination: "smtp-server-refusing-tls"

---

smtpd_tls_security_level: "encrypt"

extra_mydestination: "smtp-server-requiring-tls"

      - smtp-server-requiring-tls

      - smtp-server-refusing-tls

        10.31.127.22: "client1 smtp-server-requiring-tls"

        10.31.127.23: "client2 smtp-server-refusing-tls"

    - name: Install and configure Postfix for testing mail sending from managed servers

      block:

        - name: Install Postfix

          apt:

            name: postfix

            state: present

        - name: Purge Exim

          apt:

            name: "exim4*"

            state: absent

            purge: true

        - name: Configure Postfix

          template:

            src: "helper_smtp_main.cf.j2"

            dest: "/etc/postfix/main.cf"

            owner: root

            group: root

            mode: 0644

          notify:

            - Restart Postfix

        - name: Enable Postfix service

          service:

            name: postfix

            state: started

            enabled: true

    - name: Restart Postfix

      service:

        name: postfix

        state: restarted

# See /usr/share/postfix/main.cf.dist for a commented, more complete version

# Debian specific:  Specifying a file name will cause the first

# line of that file to be used as the name.  The Debian default

# is /etc/mailname.

#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Debian/GNU)

biff = no

# appending .domain is the MUA's job.

append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings

#delay_warning_time = 4h

readme_directory = no

# See http://www.postfix.org/COMPATIBILITY_README.html -- default to 2 on

# fresh installs.

compatibility_level = 2

# TLS parameters

smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem

smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key

smtpd_use_tls=yes

smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache

smtpd_tls_security_level = {{ smtpd_tls_security_level }}

smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for

# information on enabling SSL in the smtp client.

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination

myhostname = contrib-buster.localdomain

alias_maps = hash:/etc/aliases

alias_database = hash:/etc/aliases

myorigin = /etc/mailname

mydestination = $myhostname, localhost.localdomain, localhost, {{ extra_mydestination }}

relayhost = 

mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128

mailbox_size_limit = 0

recipient_delimiter = +

inet_interfaces = all

inet_protocols = all

def test_postfix_sends_mails_without_tls_when_unavailable(host):

    """

    Tests if Postfix sends out mails even if STARTTLS is not available

    on remote server.

    """

    # Verify that the remote host refuses to accept mails over TLS first.

    send = host.run('swaks --tls --suppress-data --to root@smtp-server-refusing-tls --server smtp-server-refusing-tls')

    assert send.rc == 29

    assert "Host did not advertise STARTTLS" in send.stderr

    message_id = str(uuid.uuid4())

    send = host.run('swaks --header %s --suppress-data --to root@smtp-server-refusing-tls --server localhost', "Message-Id: <%s>" % message_id)

    assert send.rc == 0

    with host.sudo():

        mail_log = host.file('/var/log/mail.log')

        pattern = r"postfix/cleanup\[\d+\]: (?P<queue_id>[^:]+): message-id=<%s>" % message_id

        match_result = re.search(pattern, mail_log.content_string)

        assert match_result is not None

        queue_id = match_result.group('queue_id')

        pattern = r"postfix/smtp\[\d+\]: %s: to=<root@smtp-server-refusing-tls>, relay=smtp-server-refusing-tls.*, status=sent" % queue_id

        match_result = re.search(pattern, mail_log.content_string)

        assert match_result is not None, queue_id

def test_postfix_sends_mails_over_tls_when_available(host):

    """

    Tests if Postfix sends out mails using STARTTLS if available on

    remote server (oportunistic encryption).

    """

    # Verify that the remote host refuses to accept mails without TLS first.

    send = host.run('swaks --suppress-data --to root@smtp-server-requiring-tls --server smtp-server-requiring-tls')

    assert send.rc == 23

    assert "Must issue a STARTTLS command first" in send.stdout

    message_id = str(uuid.uuid4())

    send = host.run('swaks --tls --header %s --suppress-data --to root@smtp-server-requiring-tls --server localhost', "Message-Id: <%s>" % message_id)

    assert send.rc == 0

    with host.sudo():

        mail_log = host.file('/var/log/mail.log')

        pattern = r"postfix/cleanup\[\d+\]: (?P<queue_id>[^:]+): message-id=<%s>" % message_id

        match_result = re.search(pattern, mail_log.content_string)

        assert match_result is not None

        queue_id = match_result.group('queue_id')

        pattern = r"postfix/smtp\[\d+\]: %s: to=<root@smtp-server-requiring-tls>, relay=smtp-server-requiring-tls.*, status=sent" % queue_id

        match_result = re.search(pattern, mail_log.content_string)

        assert match_result is not None, queue_id

smtp_tls_security_level = may