Replace IPSec tunnels by app-level ephemeral TLS sessions.

For some reason giraff doesn't like IPSec.  App-level TLS sessions are
less efficient, but thanks to ansible it still scales well.

23 files changed, 283 insertions, 97 deletions

diff --git a/roles/IMAP/files/etc/dovecot/conf.d/10-master.conf b/roles/IMAP/files/etc/dovecot/conf.d/10-master.conf
index d477d01..30a6f8b 100644
--- a/roles/IMAP/files/etc/dovecot/conf.d/10-master.conf
+++ b/roles/IMAP/files/etc/dovecot/conf.d/10-master.conf
@@ -15,11 +15,6 @@ default_login_user = dovenull
 default_internal_user = dovecot
 
 service imap-login {
-  inet_listener imap {
-    address = 172.16.0.1
-    port = 143
-    ssl = no
-  }
   inet_listener imaps {
     port = 993
     ssl = yes
diff --git a/roles/IMAP/files/etc/dovecot/conf.d/10-ssl.conf b/roles/IMAP/files/etc/dovecot/conf.d/10-ssl.conf
index c5e61d7..526da9c 100644
--- a/roles/IMAP/files/etc/dovecot/conf.d/10-ssl.conf
+++ b/roles/IMAP/files/etc/dovecot/conf.d/10-ssl.conf
@@ -5,18 +5,6 @@
 # SSL/TLS support: yes, no, required. <doc/wiki/SSL.txt>
 ssl = required
 
-# No need for SSL if the packets are protected by IPSec.
-local 172.16.0.1 {
-    protocol imap {
-        disable_plaintext_auth = no
-        ssl = no
-    }
-    protocol sieve {
-        disable_plaintext_auth = no
-        ssl = no
-    }
-}
-
 # PEM encoded X.509 SSL/TLS certificate and private key. They're opened before
 # dropping root privileges, so keep the key file unreadable by anyone but
 # root. Included doc/mkcert.sh can be used to easily generate self-signed
diff --git a/roles/IMAP/tasks/imap.yml b/roles/IMAP/tasks/imap.yml
index 5424485..3e93c53 100644
--- a/roles/IMAP/tasks/imap.yml
+++ b/roles/IMAP/tasks/imap.yml
@@ -62,6 +62,12 @@
         owner=vmail group=vmail
         mode=0700
 
+- name: Create directory /etc/dovecot/ssl
+  file: path=/etc/dovecot/ssl
+        state=directory
+        owner=root group=root
+        mode=0755
+
 - name: Generate a private key and a X.509 certificate for Dovecot
   command: genkeypair.sh x509
                          --pubkey=/etc/dovecot/ssl/imap.fripost.org.pem
@@ -73,6 +79,8 @@
   failed_when: r1.rc > 1
   notify:
     - Restart Dovecot
+  tags:
+    - genkey
 
 - name: Configure Dovecot
   copy: src=etc/dovecot/{{ item }}
diff --git a/roles/IMAP/tasks/mda.yml b/roles/IMAP/tasks/mda.yml
index 0358f12..4a74ed3 100644
--- a/roles/IMAP/tasks/mda.yml
+++ b/roles/IMAP/tasks/mda.yml
@@ -9,7 +9,7 @@
             dest=/etc/postfix-{{ postfix_instance[inst].name }}/main.cf
             owner=root group=root
             mode=0644
-  register: r
+  register: r1
   notify:
     - Restart Postfix
 
@@ -35,8 +35,30 @@
         owner=root group=root
         mode=0644
 
+- name: Build the Postfix relay clientcerts map
+  sudo: False
+  # smtpd_tls_fingerprint_digest MUST be sha256!
+  local_action: shell openssl x509 -in certs/postfix/{{ item }}.pem -noout -fingerprint -sha256 | sed -nr 's/^.*=(.*)/\1 {{ item }}/p'
+  with_items: groups.MX | difference([inventory_hostname]) | sort
+  register: relay_clientcerts
+  changed_when: False
+
+- name: Copy the Postfix relay clientcerts map
+  template: src=etc/postfix/relay_clientcerts.j2
+            dest=/etc/postfix-{{ postfix_instance[inst].name }}/relay_clientcerts
+            owner=root group=root
+            mode=0644
+
+- name: Compile the Postfix relay clientcerts map
+  postmap: cmd=postmap src=/etc/postfix-{{ postfix_instance[inst].name }}/relay_clientcerts db=cdb
+           owner=root group=root
+           mode=0644
+  register: r2
+  notify:
+    - Restart Postfix
+
 - name: Start Postfix
   service: name=postfix state=started
-  when: not r.changed
+  when: not (r1.changed or r2.changed)
 
 - meta: flush_handlers
diff --git a/roles/IMAP/templates/etc/postfix/main.cf.j2 b/roles/IMAP/templates/etc/postfix/main.cf.j2
index 46f64aa..40c8d32 100644
--- a/roles/IMAP/templates/etc/postfix/main.cf.j2
+++ b/roles/IMAP/templates/etc/postfix/main.cf.j2
@@ -28,11 +28,8 @@ multi_instance_enable = yes
 
 # This server is a Mail Delivery Agent
 mynetworks_style = host
-inet_interfaces  = 172.16.0.1
-{% if 'MX' in group_names %}
-                   127.0.0.1
-{% endif %}
-inet_protocols   = ipv4
+inet_interfaces  = all
+
 
 # No local delivery
 mydestination        =
@@ -64,3 +61,45 @@ recipient_canonical_maps    = pcre:$config_directory/recipient_canonical.pcre
 local_header_rewrite_clients =
 # Tolerate occasional high latency
 smtpd_timeout                = 1200s
+
+
+relay_clientcerts               = cdb:$config_directory/relay_clientcerts
+smtpd_tls_security_level        = may
+smtpd_tls_cert_file             = /etc/postfix/ssl/{{ ansible_fqdn }}.pem
+smtpd_tls_key_file              = /etc/postfix/ssl/{{ ansible_fqdn }}.key
+smtpd_tls_session_cache_database= btree:$data_directory/smtpd_tls_session_cache
+smtpd_tls_received_header       = yes
+smtpd_tls_ask_ccert             = yes
+smtpd_tls_session_cache_timeout = 3600s
+smtpd_tls_fingerprint_digest    = sha256
+
+
+strict_rfc821_envelopes = yes
+smtpd_delay_reject      = yes
+disable_vrfy_command    = yes
+
+smtpd_client_restrictions =
+    permit_mynetworks
+    permit_tls_clientcerts
+    # We are the only ones using this proxy, but if things go wrong we
+    # want to know why
+    defer
+
+smtpd_helo_required     = yes
+smtpd_helo_restrictions =
+    reject_invalid_helo_hostname
+
+smtpd_sender_restrictions =
+    reject_non_fqdn_sender
+    reject_unknown_sender_domain
+
+smtpd_recipient_restrictions =
+    # RFC requirements
+    reject_non_fqdn_recipient
+    reject_unknown_recipient_domain
+    permit_mynetworks
+    permit_tls_clientcerts
+    reject
+
+smtpd_data_restrictions =
+    reject_unauth_pipelining
diff --git a/roles/IMAP/templates/etc/postfix/relay_clientcerts.j2 b/roles/IMAP/templates/etc/postfix/relay_clientcerts.j2
new file mode 120000
index 0000000..b375aa0
--- /dev/null
+++ b/roles/IMAP/templates/etc/postfix/relay_clientcerts.j2
@@ -0,0 +1 @@
+../../../../out/templates/etc/postfix/relay_clientcerts.j2
\ No newline at end of file
diff --git a/roles/MSA/templates/etc/postfix/main.cf.j2 b/roles/MSA/templates/etc/postfix/main.cf.j2
index e3014aa..036a887 100644
--- a/roles/MSA/templates/etc/postfix/main.cf.j2
+++ b/roles/MSA/templates/etc/postfix/main.cf.j2
@@ -40,7 +40,7 @@ local_recipient_maps =
 message_size_limit  = 67108864
 recipient_delimiter = +
 
-# Forward everything to our internal mailhub
+# Forward everything to our internal outgoing proxy
 {% if 'out' in group_names %}
 relayhost     = [127.0.0.1]:{{ postfix_instance.out.port }}
 {% else %}
@@ -48,6 +48,7 @@ relayhost     = [outgoing.fripost.org]:{{ postfix_instance.out.port }}
 {% endif %}
 relay_domains =
 
+
 # Don't rewrite remote headers
 local_header_rewrite_clients     =
 # Avoid splitting the envelope and scanning messages multiple times
@@ -59,24 +60,26 @@ smtp_data_done_timeout           = 1200s
 header_checks  = pcre:$config_directory/anonymize_sender.pcre
 #content_filter = amavisfeed:unix:public/amavisfeed-antivirus
 
-# Tunnel everything through IPSec
-smtp_tls_security_level = none
+
+# TLS
 {% if 'out' in group_names %}
-smtp_bind_address       = 127.0.0.1
+smtp_tls_security_level         = none
+smtp_bind_address               = 127.0.0.1
 {% else %}
-smtp_bind_address       = 172.16.0.1
+smtp_tls_security_level         = encrypt
+smtp_tls_cert_file              = /etc/postfix/ssl/{{ ansible_fqdn }}.pem
+smtp_tls_key_file               = /etc/postfix/ssl/{{ ansible_fqdn }}.key
+smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
+smtp_tls_policy_maps            = cdb:/etc/postfix/tls_policy
+smtp_tls_fingerprint_digest     = sha256
 {% endif %}
 
-# TLS
 smtpd_tls_security_level        = encrypt
-smtpd_tls_cert_file             = /etc/ssl/certs/ssl-cert-snakeoil.pem
-smtpd_tls_key_file              = /etc/ssl/private/ssl-cert-snakeoil.key
+smtpd_tls_cert_file             = /etc/postfix/ssl/smtp.fripost.org.pem
+smtpd_tls_key_file              = /etc/postfix/ssl/private/smtp.fripost.org.key
 smtpd_tls_session_cache_database= btree:$data_directory/smtpd_tls_session_cache
 smtpd_tls_received_header       = yes
 smtpd_tls_ask_ccert             = yes
-smtpd_tls_fingerprint_digest    = sha1
-smtpd_tls_eecdh_grade           = strong
-tls_random_source               = dev:/dev/urandom
 
 # SASL
 smtpd_sasl_auth_enable          = yes
diff --git a/roles/MX/templates/etc/postfix/main.cf.j2 b/roles/MX/templates/etc/postfix/main.cf.j2
index 34e38a0..4d8e53e 100644
--- a/roles/MX/templates/etc/postfix/main.cf.j2
+++ b/roles/MX/templates/etc/postfix/main.cf.j2
@@ -41,7 +41,7 @@ local_recipient_maps =
 message_size_limit  = 67108864
 recipient_delimiter = +
 
-# Forward everything to our internal mailhub
+# Forward everything to our internal outgoing proxy
 {% if 'out' in group_names %}
 relayhost     = [127.0.0.1]:{{ postfix_instance.out.port }}
 {% else %}
@@ -49,6 +49,7 @@ relayhost     = [outgoing.fripost.org]:{{ postfix_instance.out.port }}
 {% endif %}
 relay_domains =
 
+
 # Virtual transport
 # We use a dedicated "virtual" domain to decongestion potential
 # bottlenecks on trivial_rewrite(8) due to slow LDAP lookups in
@@ -67,6 +68,7 @@ virtual_alias_maps      = pcre:$config_directory/virtual/reserved_alias.pcre
 virtual_mailbox_maps    =
 transport_maps          = cdb:$config_directory/virtual/transport
 
+
 # Don't rewrite remote headers
 local_header_rewrite_clients     =
 # Pass the client information along to the content filter
@@ -77,15 +79,20 @@ reserved-alias_recipient_limit   = 1
 # Tolerate occasional high latency
 smtp_data_done_timeout           = 1200s
 
-# Tunnel everything through IPSec
-smtp_tls_security_level = none
+
 {% if 'out' in group_names %}
-smtp_bind_address       = 127.0.0.1
+smtp_tls_security_level         = none
+smtp_bind_address               = 127.0.0.1
 {% else %}
-smtp_bind_address       = 172.16.0.1
+smtp_tls_security_level         = encrypt
+smtp_tls_cert_file              = /etc/postfix/ssl/{{ ansible_fqdn }}.pem
+smtp_tls_key_file               = /etc/postfix/ssl/{{ ansible_fqdn }}.key
+smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
+smtp_tls_policy_maps            = cdb:/etc/postfix/tls_policy
+smtp_tls_fingerprint_digest     = sha256
 {% endif %}
+smtpd_tls_security_level        = none
 
-# TLS
 smtpd_tls_security_level        = may
 smtpd_tls_cert_file             = /etc/ssl/certs/ssl-cert-snakeoil.pem
 smtpd_tls_key_file              = /etc/ssl/private/ssl-cert-snakeoil.key
@@ -93,9 +100,6 @@ smtpd_tls_CApath                = /etc/ssl/certs/
 smtpd_tls_session_cache_database= btree:$data_directory/smtpd_tls_session_cache
 smtpd_tls_received_header       = yes
 smtpd_tls_ask_ccert             = yes
-smtpd_tls_fingerprint_digest    = sha1
-smtpd_tls_eecdh_grade           = strong
-tls_random_source               = dev:/dev/urandom
 
 
 # http://en.linuxreviews.org/HOWTO_Stop_spam_using_Postfix
diff --git a/roles/MX/templates/etc/postfix/virtual/transport.j2 b/roles/MX/templates/etc/postfix/virtual/transport.j2
index 2250a71..a34dcad 100644
--- a/roles/MX/templates/etc/postfix/virtual/transport.j2
+++ b/roles/MX/templates/etc/postfix/virtual/transport.j2
@@ -3,11 +3,11 @@ reserved.locahost.localdomain   reserved-alias:
 {% if 'LDA' in group_names %}
 mda.fripost.org smtpl:[127.0.0.1]:{{ postfix_instance.IMAP.port }}
 {% else %}
-mda.fripost.org smtps:[mda.fripost.org]:{{ postfix_instance.IMAP.port }}
+mda.fripost.org smtp:[mda.fripost.org]:{{ postfix_instance.IMAP.port }}
 {% endif %}
 
 {% if 'lists' in group_names %}
 lists.fripost.org smtpl:[127.0.0.1]:{{ postfix_instance.lists.port }}
 {% else %}
-lists.fripost.org smtps:[lists.fripost.org]:{{ postfix_instance.lists.port }}
+lists.fripost.org smtp:[lists.fripost.org]:{{ postfix_instance.lists.port }}
 {% endif %}
diff --git a/roles/common/files/etc/postfix/master.cf b/roles/common/files/etc/postfix/master.cf
index e845371..70f7f4e 100644
--- a/roles/common/files/etc/postfix/master.cf
+++ b/roles/common/files/etc/postfix/master.cf
@@ -25,8 +25,6 @@ proxywrite unix -       -       n       -       1       proxymap
 smtp      unix  -       -       -       -       -       smtp
 smtpl     unix  -       -       -       -       -       smtp
   -o smtp_bind_address=127.0.0.1
-smtps     unix  -       -       -       -       -       smtp
-  -o smtp_bind_address=172.16.0.1
 relay     unix  -       -       -       -       -       smtp
 #       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
 showq     unix  n       -       -       -       -       showq
@@ -42,10 +40,7 @@ scache    unix  -       -       -       -       1       scache
 2525      inet  n       -       -       -       -       smtpd
 2526      inet  n       -       -       -       -       smtpd
 2527      inet  n       -       -       -       -       smtpd
-  -o mynetworks=0.0.0.0/0
 127.0.0.1:2580 inet n   -       -       -       -       smtpd
-127.0.0.1:smtp inet n   -       -       -       -       smtpd
-  -o inet_interfaces=127.0.0.1
 reserved-alias unix  -  n       n       -       -       pipe
   flags=Rhu user=nobody argv=/usr/local/sbin/reserved-alias.pl ${sender} ${original_recipient} @fripost.org
 mlmmj     unix  -       n       n       -       -       pipe
diff --git a/roles/common/tasks/ipsec.yml b/roles/common/tasks/ipsec.yml
index 51d717f..36807d2 100644
--- a/roles/common/tasks/ipsec.yml
+++ b/roles/common/tasks/ipsec.yml
@@ -12,14 +12,18 @@
   failed_when: r1.rc > 1
   notify:
     - Restart IPSec
+  tags:
+    - genkey
 
 - name: Fetch the public part of IPSec's host key
-  sudo: False
   # Ensure we don't fetch private data
+  sudo: False
   fetch: src=/etc/ipsec.d/certs/{{ inventory_hostname }}.pem
          dest=certs/ipsec/
          fail_on_missing=yes
          flat=yes
+  tags:
+    - genkey
 
 # Don't copy our pubkey due to a possible race condition.  Only the
 # remote machine has authority regarding its key.
diff --git a/roles/common/tasks/mail.yml b/roles/common/tasks/mail.yml
index 8572784..74919c8 100644
--- a/roles/common/tasks/mail.yml
+++ b/roles/common/tasks/mail.yml
@@ -44,7 +44,37 @@
   notify:
     - Restart Postfix
 
-- name: Update the static local Postfix database
+- name: Create directory /etc/postfix/ssl
+  file: path=/etc/postfix/ssl
+        state=directory
+        owner=root group=root
+        mode=0755
+  tags:
+    - genkey
+
+- name: Generate a private key and a X.509 certificate for Postfix
+  command: genkeypair.sh x509
+                         --pubkey=/etc/postfix/ssl/{{ ansible_fqdn }}.pem
+                         --privkey=/etc/postfix/ssl/{{ ansible_fqdn }}.key
+                         --dns={{ ansible_fqdn }}
+                         -t ecdsa -b secp384r1 -h sha512
+  register: r4
+  changed_when: r4.rc == 0
+  failed_when: r4.rc > 1
+  tags:
+    - genkey
+
+- name: Fetch Postfix's X.509 certificate
+  # Ensure we don't fetch private data
+  sudo: False
+  fetch: src=/etc/postfix/ssl/{{ ansible_fqdn }}.pem
+         dest=certs/postfix/
+         fail_on_missing=yes
+         flat=yes
+  tags:
+    - genkey
+
+- name: Compile the static local Postfix database
   postmap: cmd=postalias src=/etc/aliases db=cdb
            owner=root group=root
            mode=0644
@@ -53,8 +83,33 @@
 - name: Delete /etc/aliases.db
   file: path=/etc/aliases.db state=absent
 
+- name: Build the Postfix TLS policy map
+  sudo: False
+  # smtp_tls_fingerprint_digest MUST be sha256!
+  local_action: shell openssl x509 -in certs/postfix/{{ item }}.pem -noout -fingerprint -sha256 | cut -d= -f2
+  with_items: groups.out | sort
+  register: tls_policy
+  changed_when: False
+  when: "'out' not in group_names"
+
+- name: Copy the Postfix TLS policy map
+  template: src=etc/postfix/tls_policy.j2
+            dest=/etc/postfix/tls_policy
+            owner=root group=root
+            mode=0644
+  when: "'out' not in group_names"
+
+- name: Compile the Postfix TLS policy map
+  postmap: cmd=postmap src=/etc/postfix/tls_policy db=cdb
+           owner=root group=root
+           mode=0644
+  when: "'out' not in group_names"
+  register: r5
+  notify:
+    - Restart Postfix
+
 - name: Start Postfix
   service: name=postfix state=started
-  when: not (r1.changed or r2.changed or r3.changed)
+  when: not (r1.changed or r2.changed or r3.changed or r5.changed)
 
 - meta: flush_handlers
diff --git a/roles/common/tasks/main.yml b/roles/common/tasks/main.yml
index 0048443..464abd0 100644
--- a/roles/common/tasks/main.yml
+++ b/roles/common/tasks/main.yml
@@ -15,8 +15,7 @@
         owner=root group=root
         mode=0755
   tags:
-    - genkeypair
-- include: ipsec.yml    tags=strongswan,ipsec
+    - genkey
 - include: logging.yml  tags=logging
 - include: ntp.yml      tags=ntp
 - include: mail.yml     tags=mail,postfix
diff --git a/roles/common/templates/etc/iptables/services.j2 b/roles/common/templates/etc/iptables/services.j2
index 923aa35..3e31f04 100644
--- a/roles/common/templates/etc/iptables/services.j2
+++ b/roles/common/templates/etc/iptables/services.j2
@@ -4,9 +4,6 @@
 # direction              protocol     destination port            source port
 # (in|out|inout)[46]?    (tcp|udp|..) (port|port:port|port,port)  (port|port:port|port,port)
 
-inout   udp     500      500                            # ISAKMP
-#inout   udp     4500    4500    # IPSec NAT Traversal
-
 out     tcp     80,443                                  # HTTP/HTTPS
 out     udp     53                                      # DNS
 out     udp     67                                      # DHCP
@@ -20,15 +17,23 @@ in      tcp     {{ ansible_ssh_port|default('22') }}    # SSH
 in      tcp     25                                      # SMTP
 {% endif %}
 {% if 'out' in group_names %}
-#out     tcp     25                                     # SMTP
+in      tcp     {{ postfix_instance.out.port }}
+out     tcp     25                                      # SMTP
+{% else %}
+out     tcp     {{ postfix_instance.out.port }}
 {% endif %}
 {% if 'IMAP' in group_names %}
 in      tcp     993                                     # IMAPS
 in      tcp     4190                                    # ManageSieve
 {% endif %}
+{% if 'MDA' in group_names %}
+in      tcp     {{ postfix_instance.mda.port }}
+{% endif %}
 {% if 'MSA' in group_names %}
 in      tcp     587                                     # SMTP-AUTH
 {% endif %}
 {% if 'webmail' in group_names %}
 in     tcp      80,443                                  # HTTP/HTTPS
+out    tcp      993                                     # IMAP # TODO imapc
+out    tcp      4190
 {% endif %}
diff --git a/roles/common/templates/etc/postfix/main.cf.j2 b/roles/common/templates/etc/postfix/main.cf.j2
index 70d4b98..1abce71 100644
--- a/roles/common/templates/etc/postfix/main.cf.j2
+++ b/roles/common/templates/etc/postfix/main.cf.j2
@@ -17,7 +17,6 @@ append_dot_mydomain = no
 # This server is for internal use only
 mynetworks_style = host
 inet_interfaces  = loopback-only
-inet_protocols   = ipv4
 
 # No local delivery
 mydestination        =
@@ -30,7 +29,7 @@ default_database_type = cdb
 virtual_alias_maps    = cdb:/etc/aliases
 alias_database        = $virtual_alias_maps
 
-# Forward everything to our internal mailhub
+# Forward everything to our internal outgoing proxy
 {% if 'out' in group_names %}
 relayhost     = [127.0.0.1]:{{ postfix_instance.out.port }}
 {% else %}
@@ -38,14 +37,18 @@ relayhost     = [outgoing.fripost.org]:{{ postfix_instance.out.port }}
 {% endif %}
 relay_domains =
 
-# Tunnel everything through IPSec
-smtp_tls_security_level  = none
 {% if 'out' in group_names %}
-smtp_bind_address        = 127.0.0.1
+smtp_tls_security_level         = none
+smtp_bind_address               = 127.0.0.1
 {% else %}
-smtp_bind_address        = 172.16.0.1
+smtp_tls_security_level         = encrypt
+smtp_tls_cert_file              = $config_directory/ssl/{{ ansible_fqdn }}.pem
+smtp_tls_key_file               = $config_directory/ssl/{{ ansible_fqdn }}.key
+smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
+smtp_tls_policy_maps            = cdb:$config_directory/tls_policy
+smtp_tls_fingerprint_digest     = sha256
 {% endif %}
-smtpd_tls_security_level = none
+smtpd_tls_security_level        = none
 
 # Turn off all TCP/IP listener ports except that dedicated to
 # samhain(8), which sadly cannot use pickup through the sendmail binary.
diff --git a/roles/common/templates/etc/postfix/tls_policy.j2 b/roles/common/templates/etc/postfix/tls_policy.j2
new file mode 100644
index 0000000..b4fc453
--- /dev/null
+++ b/roles/common/templates/etc/postfix/tls_policy.j2
@@ -0,0 +1,6 @@
+# {{ ansible_managed }}
+
+[outgoing.fripost.org]:{{ postfix_instance.out.port }} fingerprint ciphers=high protocols=TLSv1.2
+{% for x in tls_policy.results %}
+   match={{ x.stdout }}
+{% endfor %}
diff --git a/roles/lists/templates/etc/postfix/main.cf.j2 b/roles/lists/templates/etc/postfix/main.cf.j2
index 083fa2b..b7a82fe 100644
--- a/roles/lists/templates/etc/postfix/main.cf.j2
+++ b/roles/lists/templates/etc/postfix/main.cf.j2
@@ -66,11 +66,24 @@ smtp_destination_recipient_limit = 1000
 smtp_data_done_timeout       = 1200s
 smtpd_timeout                = 1200s
 
-# Tunnel everything through IPSec
-smtp_tls_security_level  = none
+
+# Forward everything to our internal outgoing proxy
+{% if 'out' in group_names %}
+relayhost     = [127.0.0.1]:{{ postfix_instance.out.port }}
+{% else %}
+relayhost     = [outgoing.fripost.org]:{{ postfix_instance.out.port }}
+{% endif %}
+relay_domains =
+
 {% if 'out' in group_names %}
-smtp_bind_address        = 127.0.0.1
+smtp_tls_security_level         = none
+smtp_bind_address               = 127.0.0.1
 {% else %}
-smtp_bind_address        = 172.16.0.1
+smtp_tls_security_level         = encrypt
+smtp_tls_cert_file              = $config_directory/ssl/{{ ansible_fqdn }}.pem
+smtp_tls_key_file               = $config_directory/ssl/{{ ansible_fqdn }}.key
+smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
+smtp_tls_policy_maps            = cdb:$config_directory/tls_policy
+smtp_tls_fingerprint_digest     = sha256
 {% endif %}
-smtpd_tls_security_level = none
+smtpd_tls_security_level        = none
diff --git a/roles/out/tasks/main.yml b/roles/out/tasks/main.yml
index 4bf4363..8bd8bbb 100644
--- a/roles/out/tasks/main.yml
+++ b/roles/out/tasks/main.yml
@@ -10,8 +10,30 @@
   notify:
     - Restart Postfix
 
+- name: Build the Postfix relay clientcerts map
+  sudo: False
+  # smtpd_tls_fingerprint_digest MUST be sha256!
+  local_action: shell openssl x509 -in certs/postfix/{{ item }}.pem -noout -fingerprint -sha256 | sed -nr 's/^.*=(.*)/\1 {{ item }}/p'
+  with_items: groups.all | difference([inventory_hostname]) | sort
+  register: relay_clientcerts
+  changed_when: False
+
+- name: Copy the Postfix relay clientcerts map
+  template: src=etc/postfix/relay_clientcerts.j2
+            dest=/etc/postfix-{{ postfix_instance[inst].name }}/relay_clientcerts
+            owner=root group=root
+            mode=0644
+
+- name: Compile the Postfix relay clientcerts map
+  postmap: cmd=postmap src=/etc/postfix-{{ postfix_instance[inst].name }}/relay_clientcerts db=cdb
+           owner=root group=root
+           mode=0644
+  register: r2
+  notify:
+    - Restart Postfix
+
 - name: Start Postfix
   service: name=postfix state=started
-  when: not r.changed
+  when: not (r1.changed or r2.changed)
 
 - meta: flush_handlers
diff --git a/roles/out/templates/etc/postfix/main.cf.j2 b/roles/out/templates/etc/postfix/main.cf.j2
index 1a7985f..11bcc10 100644
--- a/roles/out/templates/etc/postfix/main.cf.j2
+++ b/roles/out/templates/etc/postfix/main.cf.j2
@@ -1,5 +1,5 @@
 ########################################################################
-# Outgoing MTA configuration
+# Outgoing MTA (outgoing SMTP proxy) configuration
 #
 # {{ ansible_managed }}
 # Do NOT edit this file directly!
@@ -19,7 +19,7 @@ append_dot_mydomain = no
 
 # Turn off all TCP/IP listener ports except that necessary for the
 # outgoing SMTP proxy.
-master_service_disable = !2525.inet inet
+master_service_disable = !{{ postfix_instance.out.port }}.inet inet
 
 queue_directory       = /var/spool/postfix-{{ postfix_instance[inst].name }}
 data_directory        = /var/lib/postfix-{{ postfix_instance[inst].name }}
@@ -27,10 +27,8 @@ multi_instance_group  = {{ postfix_instance[inst].group | default('') }}
 multi_instance_name   = postfix-{{ postfix_instance[inst].name }}
 multi_instance_enable = yes
 
-# Accept everything coming through IPSec.
-# TODO: this should our virtual private subnetwork
-mynetworks      = 0.0.0.0/0
-inet_interfaces = 172.16.0.1, 127.0.0.1
+mynetworks_style = host
+inet_interfaces  = all
 
 # No local delivery
 mydestination        =
@@ -42,8 +40,8 @@ local_recipient_maps =
 message_size_limit  = 67108864
 recipient_delimiter = +
 
-relay_domains           =
-relay_transport         = error:5.3.2 Relay Transport unavailable
+relay_domains       =
+relay_transport     = error:5.3.2 Relay Transport unavailable
 
 # All header rewriting happens upstream
 local_header_rewrite_clients =
@@ -51,13 +49,29 @@ local_header_rewrite_clients =
 
 smtp_tls_security_level         = may
 smtp_tls_note_starttls_offer    = yes
-smtp_tls_cert_file              = /etc/postfix-out/ssl/smtp.fripost.org.pem
-smtp_tls_key_file               = /etc/postfix-out/ssl/smtp.fripost.org.key
-smtp_tls_CApath                 = /etc/ssl/certs/
 smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
-smtp_tls_fingerprint_digest     = sha1
-tls_random_source               = dev:/dev/urandom
 
+relay_clientcerts               = cdb:$config_directory/relay_clientcerts
+smtpd_tls_security_level        = may
+smtpd_tls_cert_file             = /etc/postfix/ssl/{{ ansible_fqdn }}.pem
+smtpd_tls_key_file              = /etc/postfix/ssl/{{ ansible_fqdn }}.key
+smtpd_tls_session_cache_database= btree:$data_directory/smtpd_tls_session_cache
+smtpd_tls_received_header       = yes
+smtpd_tls_ask_ccert             = yes
+smtpd_tls_session_cache_timeout = 3600s
+smtpd_tls_fingerprint_digest    = sha256
+
+
+strict_rfc821_envelopes = yes
+smtpd_delay_reject      = yes
+disable_vrfy_command    = yes
+
+smtpd_client_restrictions =
+    permit_mynetworks
+    permit_tls_clientcerts
+    # We are the only ones using this proxy, but if things go wrong we
+    # want to know why
+    defer
 
 smtpd_helo_required     = yes
 smtpd_helo_restrictions =
@@ -72,7 +86,8 @@ smtpd_recipient_restrictions =
     reject_non_fqdn_recipient
     reject_unknown_recipient_domain
     permit_mynetworks
-    reject_unauth_destination
+    permit_tls_clientcerts
+    reject
 
 smtpd_data_restrictions =
     reject_unauth_pipelining
diff --git a/roles/out/templates/etc/postfix/relay_clientcerts.j2 b/roles/out/templates/etc/postfix/relay_clientcerts.j2
new file mode 100644
index 0000000..3f724ea
--- /dev/null
+++ b/roles/out/templates/etc/postfix/relay_clientcerts.j2
@@ -0,0 +1,5 @@
+# {{ ansible_managed }}
+
+{% for x in relay_clientcerts.results %}
+{{ x.stdout }}
+{% endfor %}
diff --git a/roles/webmail/tasks/roundcube.yml b/roles/webmail/tasks/roundcube.yml
index 2085974..feb38ee 100644
--- a/roles/webmail/tasks/roundcube.yml
+++ b/roles/webmail/tasks/roundcube.yml
@@ -89,6 +89,8 @@
   failed_when: r1.rc > 1
   notify:
     - Restart Nginx
+  tags:
+    - genkey
 
 - name: Copy /etc/nginx/sites-available/roundcube
   copy: src=etc/nginx/sites-available/roundcube
diff --git a/roles/webmail/templates/etc/postfix/main.cf.j2 b/roles/webmail/templates/etc/postfix/main.cf.j2
index b070881..595f618 100644
--- a/roles/webmail/templates/etc/postfix/main.cf.j2
+++ b/roles/webmail/templates/etc/postfix/main.cf.j2
@@ -40,7 +40,7 @@ local_recipient_maps =
 message_size_limit  = 67108864
 recipient_delimiter = +
 
-# Forward everything to our internal mailhub
+# Forward everything to our internal outgoing proxy
 {% if 'out' in group_names %}
 relayhost     = [127.0.0.1]:{{ postfix_instance.out.port }}
 {% else %}
@@ -48,6 +48,7 @@ relayhost     = [outgoing.fripost.org]:{{ postfix_instance.out.port }}
 {% endif %}
 relay_domains =
 
+
 # Don't rewrite remote headers
 local_header_rewrite_clients     =
 # Avoid splitting the envelope and scanning messages multiple times
@@ -55,17 +56,18 @@ smtp_destination_recipient_limit = 1000
 # Tolerate occasional high latency
 smtp_data_done_timeout           = 1200s
 
-# Pass the mail to the antivirus
-#content_filter = amavisfeed:unix:public/amavisfeed-antivirus
-
-# Tunnel everything through IPSec
-smtp_tls_security_level  = none
 {% if 'out' in group_names %}
-smtp_bind_address        = 127.0.0.1
+smtp_tls_security_level         = none
+smtp_bind_address               = 127.0.0.1
 {% else %}
-smtp_bind_address        = 172.16.0.1
+smtp_tls_security_level         = encrypt
+smtp_tls_cert_file              = /etc/postfix/ssl/{{ ansible_fqdn }}.pem
+smtp_tls_key_file               = /etc/postfix/ssl/{{ ansible_fqdn }}.key
+smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
+smtp_tls_policy_maps            = cdb:/etc/postfix/tls_policy
+smtp_tls_fingerprint_digest     = sha256
 {% endif %}
-smtpd_tls_security_level = none
+smtpd_tls_security_level        = none
 
 
 strict_rfc821_envelopes = yes
diff --git a/roles/webmail/templates/usr/share/roundcube/plugins/managesieve/config.inc.php.j2 b/roles/webmail/templates/usr/share/roundcube/plugins/managesieve/config.inc.php.j2
index c716ddc..d88a09a 100644
--- a/roles/webmail/templates/usr/share/roundcube/plugins/managesieve/config.inc.php.j2
+++ b/roles/webmail/templates/usr/share/roundcube/plugins/managesieve/config.inc.php.j2
@@ -26,7 +26,7 @@ $rcmail_config['managesieve_auth_pw'] = null;
 // use or not TLS for managesieve server connection
 // it's because I've problems with TLS and dovecot's managesieve plugin
 // and it's not needed on localhost
-$rcmail_config['managesieve_usetls'] = FALSE;
+$rcmail_config['managesieve_usetls'] = TRUE;
 
 // default contents of filters script (eg. default spam filter)
 $rcmail_config['managesieve_default'] = '/etc/dovecot/sieve/global';