diff --git a/Vagrantfile b/Vagrantfile
index b990d1311..c919f16a0 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -10,10 +10,12 @@ Vagrant.configure(VAGRANTFILE_API_VERSION) do |config|
   config.vm.define "sender" do |sender|
     sender.vm.network "private_network", ip: "192.168.33.5"
     sender.vm.hostname = "sender.example.com"
+    config.vm.synced_folder "vm-postfix-config-sender", "/etc/postfix"
   end
   config.vm.define "valid" do |valid|
     valid.vm.network "private_network", ip: "192.168.33.7"
     valid.vm.hostname = "valid-example-recipient.com"
+    config.vm.synced_folder "vm-postfix-config-valid", "/etc/postfix"
   end
   config.vm.provision :shell, path: "vagrant-bootstrap.sh"
 
@@ -21,4 +23,5 @@ Vagrant.configure(VAGRANTFILE_API_VERSION) do |config|
  #   vb.gui = true
      vb.customize ["modifyvm", :id, "--memory", "256"]
   end
+
 end
diff --git a/vagrant-bootstrap.sh b/vagrant-bootstrap.sh
index 215abacfd..9ec1e3d11 100755
--- a/vagrant-bootstrap.sh
+++ b/vagrant-bootstrap.sh
@@ -4,7 +4,7 @@ export DEBIAN_FRONTEND=noninteractive
 
 apt-get update -q
 apt-get install -q -y -o Dpkg::Options::="--force-confdef" -o Dpkg::Options::="--force-confold" \
-  postfix dnsmasq mutt
+  postfix dnsmasq mutt vim
 
 # Provide hostnames so the boxes can talk to each other. DNSMasq will also serve
 # results to each box based on these contents.
diff --git a/vm-postfix-config-sender/dynamicmaps.cf b/vm-postfix-config-sender/dynamicmaps.cf
new file mode 100644
index 000000000..1c48bdcde
--- /dev/null
+++ b/vm-postfix-config-sender/dynamicmaps.cf
@@ -0,0 +1,6 @@
+# Postfix dynamic maps configuration file.
+#
+#type	location of .so file			open function	(mkmap func)
+#====	================================	=============	============
+tcp	/usr/lib/postfix/dict_tcp.so		dict_tcp_open	
+sqlite	/usr/lib/postfix/dict_sqlite.so		dict_sqlite_open	
diff --git a/vm-postfix-config-sender/main.cf b/vm-postfix-config-sender/main.cf
new file mode 100644
index 000000000..2d926a657
--- /dev/null
+++ b/vm-postfix-config-sender/main.cf
@@ -0,0 +1,42 @@
+# 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 $mail_name (Ubuntu)
+biff = no
+
+# appending .domain is the MUA's job.
+append_dot_mydomain = no
+
+# Uncomment the next line to generate "delayed mail" warnings
+#delay_warning_time = 4h
+
+readme_directory = no
+
+# TLS parameters
+smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
+smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
+smtpd_use_tls=yes
+smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
+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.
+
+myhostname = sender.example.com
+alias_maps = hash:/etc/aliases
+alias_database = hash:/etc/aliases
+myorigin = /etc/mailname
+mydestination = sender.example.com, localhost.example.com, , localhost
+relayhost = 
+mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
+mailbox_size_limit = 0
+recipient_delimiter = +
+inet_interfaces = all
+
+#STARTTLS EVERYWHERE MAGIC STARTS HERE
+smtp_tls_policy_maps = texthash:/etc/postfix/tls_policy
diff --git a/vm-postfix-config-sender/master.cf b/vm-postfix-config-sender/master.cf
new file mode 100644
index 000000000..3df29d8a9
--- /dev/null
+++ b/vm-postfix-config-sender/master.cf
@@ -0,0 +1,113 @@
+#
+# Postfix master process configuration file.  For details on the format
+# of the file, see the master(5) manual page (command: "man 5 master").
+#
+# Do not forget to execute "postfix reload" after editing this file.
+#
+# ==========================================================================
+# service type  private unpriv  chroot  wakeup  maxproc command + args
+#               (yes)   (yes)   (yes)   (never) (100)
+# ==========================================================================
+smtp      inet  n       -       -       -       -       smtpd
+#smtp      inet  n       -       -       -       1       postscreen
+#smtpd     pass  -       -       -       -       -       smtpd
+#dnsblog   unix  -       -       -       -       0       dnsblog
+#tlsproxy  unix  -       -       -       -       0       tlsproxy
+#submission inet n       -       -       -       -       smtpd
+#  -o syslog_name=postfix/submission
+#  -o smtpd_tls_security_level=encrypt
+#  -o smtpd_sasl_auth_enable=yes
+#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
+#  -o milter_macro_daemon_name=ORIGINATING
+#smtps     inet  n       -       -       -       -       smtpd
+#  -o syslog_name=postfix/smtps
+#  -o smtpd_tls_wrappermode=yes
+#  -o smtpd_sasl_auth_enable=yes
+#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
+#  -o milter_macro_daemon_name=ORIGINATING
+#628       inet  n       -       -       -       -       qmqpd
+pickup    fifo  n       -       -       60      1       pickup
+cleanup   unix  n       -       -       -       0       cleanup
+qmgr      fifo  n       -       n       300     1       qmgr
+#qmgr     fifo  n       -       n       300     1       oqmgr
+tlsmgr    unix  -       -       -       1000?   1       tlsmgr
+rewrite   unix  -       -       -       -       -       trivial-rewrite
+bounce    unix  -       -       -       -       0       bounce
+defer     unix  -       -       -       -       0       bounce
+trace     unix  -       -       -       -       0       bounce
+verify    unix  -       -       -       -       1       verify
+flush     unix  n       -       -       1000?   0       flush
+proxymap  unix  -       -       n       -       -       proxymap
+proxywrite unix -       -       n       -       1       proxymap
+smtp      unix  -       -       -       -       -       smtp
+relay     unix  -       -       -       -       -       smtp
+#       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
+showq     unix  n       -       -       -       -       showq
+error     unix  -       -       -       -       -       error
+retry     unix  -       -       -       -       -       error
+discard   unix  -       -       -       -       -       discard
+local     unix  -       n       n       -       -       local
+virtual   unix  -       n       n       -       -       virtual
+lmtp      unix  -       -       -       -       -       lmtp
+anvil     unix  -       -       -       -       1       anvil
+scache    unix  -       -       -       -       1       scache
+#
+# ====================================================================
+# Interfaces to non-Postfix software. Be sure to examine the manual
+# pages of the non-Postfix software to find out what options it wants.
+#
+# Many of the following services use the Postfix pipe(8) delivery
+# agent.  See the pipe(8) man page for information about ${recipient}
+# and other message envelope options.
+# ====================================================================
+#
+# maildrop. See the Postfix MAILDROP_README file for details.
+# Also specify in main.cf: maildrop_destination_recipient_limit=1
+#
+maildrop  unix  -       n       n       -       -       pipe
+  flags=DRhu user=vmail argv=/usr/bin/maildrop -d ${recipient}
+#
+# ====================================================================
+#
+# Recent Cyrus versions can use the existing "lmtp" master.cf entry.
+#
+# Specify in cyrus.conf:
+#   lmtp    cmd="lmtpd -a" listen="localhost:lmtp" proto=tcp4
+#
+# Specify in main.cf one or more of the following:
+#  mailbox_transport = lmtp:inet:localhost
+#  virtual_transport = lmtp:inet:localhost
+#
+# ====================================================================
+#
+# Cyrus 2.1.5 (Amos Gouaux)
+# Also specify in main.cf: cyrus_destination_recipient_limit=1
+#
+#cyrus     unix  -       n       n       -       -       pipe
+#  user=cyrus argv=/cyrus/bin/deliver -e -r ${sender} -m ${extension} ${user}
+#
+# ====================================================================
+# Old example of delivery via Cyrus.
+#
+#old-cyrus unix  -       n       n       -       -       pipe
+#  flags=R user=cyrus argv=/cyrus/bin/deliver -e -m ${extension} ${user}
+#
+# ====================================================================
+#
+# See the Postfix UUCP_README file for configuration details.
+#
+uucp      unix  -       n       n       -       -       pipe
+  flags=Fqhu user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient)
+#
+# Other external delivery methods.
+#
+ifmail    unix  -       n       n       -       -       pipe
+  flags=F user=ftn argv=/usr/lib/ifmail/ifmail -r $nexthop ($recipient)
+bsmtp     unix  -       n       n       -       -       pipe
+  flags=Fq. user=bsmtp argv=/usr/lib/bsmtp/bsmtp -t$nexthop -f$sender $recipient
+scalemail-backend unix	-	n	n	-	2	pipe
+  flags=R user=scalemail argv=/usr/lib/scalemail/bin/scalemail-store ${nexthop} ${user} ${extension}
+mailman   unix  -       n       n       -       -       pipe
+  flags=FR user=list argv=/usr/lib/mailman/bin/postfix-to-mailman.py
+  ${nexthop} ${user}
+
diff --git a/vm-postfix-config-sender/tls_policy b/vm-postfix-config-sender/tls_policy
new file mode 100644
index 000000000..7792bad7f
--- /dev/null
+++ b/vm-postfix-config-sender/tls_policy
@@ -0,0 +1 @@
+valid-example-recipient.com encrypt protocols=TLSv1.2