Moving encrypt, sign and send logic from gateway (SMTP) to a MailService

8 files changed, 639 insertions, 603 deletions

diff --git a/mail/changes/feature-6357_factor_encryptio_and_sending_out_of_encrypted_message b/mail/changes/feature-6357_factor_encryptio_and_sending_out_of_encrypted_message
new file mode 100644
index 0000000..6b95c6a
--- /dev/null
+++ b/mail/changes/feature-6357_factor_encryptio_and_sending_out_of_encrypted_message
@@ -0,0 +1 @@
+- Creates a OutgoingMail class that has the logic for encrypting, signing and sending messages. Factors that logic out of EncryptedMessage so it can be used by other clients (Closes: #6357)
diff --git a/mail/src/leap/mail/service.py b/mail/src/leap/mail/service.py
new file mode 100644
index 0000000..d595067
--- /dev/null
+++ b/mail/src/leap/mail/service.py
@@ -0,0 +1,384 @@
+# -*- coding: utf-8 -*-
+# service.py
+# Copyright (C) 2013 LEAP
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program. If not, see <http://www.gnu.org/licenses/>.
+import re
+from StringIO import StringIO
+from email.parser import Parser
+from email.mime.application import MIMEApplication
+
+from OpenSSL import SSL
+
+from twisted.mail import smtp
+from twisted.internet import reactor
+from twisted.internet import defer
+from twisted.internet.threads import deferToThread
+from twisted.protocols.amp import ssl
+from twisted.python import log
+
+from leap.common.check import leap_assert_type, leap_assert
+from leap.common.events import proto, signal
+from leap.keymanager import KeyManager
+from leap.keymanager.openpgp import OpenPGPKey
+from leap.keymanager.errors import KeyNotFound
+from leap.mail import __version__
+from leap.mail.utils import validate_address
+from leap.mail.smtp.rfc3156 import MultipartEncrypted
+from leap.mail.smtp.rfc3156 import MultipartSigned
+from leap.mail.smtp.rfc3156 import encode_base64_rec
+from leap.mail.smtp.rfc3156 import RFC3156CompliantGenerator
+from leap.mail.smtp.rfc3156 import PGPSignature
+from leap.mail.smtp.rfc3156 import PGPEncrypted
+
+
+class SSLContextFactory(ssl.ClientContextFactory):
+    def __init__(self, cert, key):
+        self.cert = cert
+        self.key = key
+
+    def getContext(self):
+        self.method = SSL.TLSv1_METHOD  # SSLv23_METHOD
+        ctx = ssl.ClientContextFactory.getContext(self)
+        ctx.use_certificate_file(self.cert)
+        ctx.use_privatekey_file(self.key)
+        return ctx
+
+
+class OutgoingMail:
+    """
+    A service for handling encrypted mail.
+    """
+
+    FOOTER_STRING = "I prefer encrypted email"
+
+    def __init__(self, from_address, keymanager, cert, key, host, port):
+        """
+        Initialize the mail service.
+
+        :param from_address: The sender address.
+        :type from_address: str
+        :param keymanager: A KeyManager for retrieving recipient's keys.
+        :type keymanager: leap.common.keymanager.KeyManager
+        :param cert: The client certificate for SSL authentication.
+        :type cert: str
+        :param key: The client private key for SSL authentication.
+        :type key: str
+        :param host: The hostname of the remote SMTP server.
+        :type host: str
+        :param port: The port of the remote SMTP server.
+        :type port: int
+        """
+
+        # XXX: should we keep these checks?
+        # assert params
+        leap_assert_type(keymanager, KeyManager)
+        leap_assert_type(host, str)
+        leap_assert(host != '')
+        leap_assert_type(port, int)
+        leap_assert(port is not 0)
+        leap_assert_type(cert, unicode)
+        leap_assert(cert != '')
+        leap_assert_type(key, unicode)
+        leap_assert(key != '')
+
+        self._port = port
+        self._host = host
+        self._key = key
+        self._cert = cert
+        self._from_address = from_address
+        self._keymanager = keymanager
+
+    def send_message(self, raw, recipient):
+        """
+        Sends a message to a recipient. Maybe encrypts and signs.
+
+        :param raw: The raw message
+        :type raw: str
+        :param recipient: The recipient for the message
+        :type recipient: smtp.User
+        :return: a deferred which delivers the message when fired
+        """
+        d = deferToThread(lambda: self._maybe_encrypt_and_sign(raw, recipient))
+        d.addCallback(self._route_msg)
+        d.addErrback(self.sendError)
+
+        return d
+
+    def sendSuccess(self, smtp_sender_result):
+        """
+        Callback for a successful send.
+
+        :param smtp_sender_result: The result from the ESMTPSender from _route_msg
+        :type smtp_sender_result: tuple(int, list(tuple))
+        """
+        dest_addrstr = smtp_sender_result[1][0][0]
+        log.msg('Message sent to %s' % dest_addrstr)
+        signal(proto.SMTP_SEND_MESSAGE_SUCCESS, dest_addrstr)
+
+    def sendError(self, failure):
+        """
+        Callback for an unsuccessfull send.
+
+        :param e: The result from the last errback.
+        :type e: anything
+        """
+        # XXX: need to get the address from the exception to send signal
+        # signal(proto.SMTP_SEND_MESSAGE_ERROR, self._user.dest.addrstr)
+        err = failure.value
+        log.err(err)
+        raise err
+
+    def _route_msg(self, encrypt_and_sign_result):
+        """
+        Sends the msg using the ESMTPSenderFactory.
+
+        :param encrypt_and_sign_result: A tuple containing the 'maybe' encrypted message and the recipient
+        :type encrypt_and_sign_result: tuple
+        """
+        message, recipient = encrypt_and_sign_result
+        log.msg("Connecting to SMTP server %s:%s" % (self._host, self._port))
+        msg = message.as_string(False)
+
+        # we construct a defer to pass to the ESMTPSenderFactory
+        d = defer.Deferred()
+        d.addCallbacks(self.sendSuccess, self.sendError)
+        # we don't pass an ssl context factory to the ESMTPSenderFactory
+        # because ssl will be handled by reactor.connectSSL() below.
+        factory = smtp.ESMTPSenderFactory(
+            "",  # username is blank because client auth is done on SSL protocol level
+            "",  # password is blank because client auth is done on SSL protocol level
+            self._from_address,
+            recipient.dest.addrstr,
+            StringIO(msg),
+            d,
+            heloFallback=True,
+            requireAuthentication=False,
+            requireTransportSecurity=True)
+        factory.domain = __version__
+        signal(proto.SMTP_SEND_MESSAGE_START, recipient.dest.addrstr)
+        reactor.connectSSL(
+            self._host, self._port, factory,
+            contextFactory=SSLContextFactory(self._cert, self._key))
+
+
+    def _maybe_encrypt_and_sign(self, raw, recipient):
+        """
+        Attempt to encrypt and sign the outgoing message.
+
+        The behaviour of this method depends on:
+
+            1. the original message's content-type, and
+            2. the availability of the recipient's public key.
+
+        If the original message's content-type is "multipart/encrypted", then
+        the original message is not altered. For any other content-type, the
+        method attempts to fetch the recipient's public key. If the
+        recipient's public key is available, the message is encrypted and
+        signed; otherwise it is only signed.
+
+        Note that, if the C{encrypted_only} configuration is set to True and
+        the recipient's public key is not available, then the recipient
+        address would have been rejected in SMTPDelivery.validateTo().
+
+        The following table summarizes the overall behaviour of the gateway:
+
+        +---------------------------------------------------+----------------+
+        | content-type        | rcpt pubkey | enforce encr. | action         |
+        +---------------------+-------------+---------------+----------------+
+        | multipart/encrypted | any         | any           | pass           |
+        | other               | available   | any           | encrypt + sign |
+        | other               | unavailable | yes           | reject         |
+        | other               | unavailable | no            | sign           |
+        +---------------------+-------------+---------------+----------------+
+
+        :param raw: The raw message
+        :type raw: str
+        :param recipient: The recipient for the message
+        :type: recipient: smtp.User
+
+        """
+        # pass if the original message's content-type is "multipart/encrypted"
+        lines = raw.split('\r\n')
+        origmsg = Parser().parsestr(raw)
+
+        if origmsg.get_content_type() == 'multipart/encrypted':
+            return origmsg
+
+        from_address = validate_address(self._from_address)
+        username, domain = from_address.split('@')
+
+        # add a nice footer to the outgoing message
+        # XXX: footer will eventually optional or be removed
+        if origmsg.get_content_type() == 'text/plain':
+            lines.append('--')
+            lines.append('%s - https://%s/key/%s' %
+                         (self.FOOTER_STRING, domain, username))
+            lines.append('')
+
+        origmsg = Parser().parsestr('\r\n'.join(lines))
+
+        # get sender and recipient data
+        signkey = self._keymanager.get_key(from_address, OpenPGPKey, private=True)
+        log.msg("Will sign the message with %s." % signkey.fingerprint)
+        to_address = validate_address(recipient.dest.addrstr)
+        try:
+            # try to get the recipient pubkey
+            pubkey = self._keymanager.get_key(to_address, OpenPGPKey)
+            log.msg("Will encrypt the message to %s." % pubkey.fingerprint)
+            signal(proto.SMTP_START_ENCRYPT_AND_SIGN,
+                   "%s,%s" % (self._from_address, to_address))
+            newmsg = self._encrypt_and_sign(origmsg, pubkey, signkey)
+
+            signal(proto.SMTP_END_ENCRYPT_AND_SIGN,
+                   "%s,%s" % (self._from_address, to_address))
+        except KeyNotFound:
+            # at this point we _can_ send unencrypted mail, because if the
+            # configuration said the opposite the address would have been
+            # rejected in SMTPDelivery.validateTo().
+            log.msg('Will send unencrypted message to %s.' % to_address)
+            signal(proto.SMTP_START_SIGN, self._from_address)
+            newmsg = self._sign(origmsg, signkey)
+            signal(proto.SMTP_END_SIGN, self._from_address)
+        return newmsg, recipient
+
+
+    def _encrypt_and_sign(self, origmsg, pubkey, signkey):
+        """
+        Create an RFC 3156 compliang PGP encrypted and signed message using
+        C{pubkey} to encrypt and C{signkey} to sign.
+
+        :param origmsg: The original message
+        :type origmsg: email.message.Message
+        :param pubkey: The public key used to encrypt the message.
+        :type pubkey: OpenPGPKey
+        :param signkey: The private key used to sign the message.
+        :type signkey: OpenPGPKey
+        :return: The encrypted and signed message
+        :rtype: MultipartEncrypted
+        """
+        # create new multipart/encrypted message with 'pgp-encrypted' protocol
+        newmsg = MultipartEncrypted('application/pgp-encrypted')
+        # move (almost) all headers from original message to the new message
+        self._fix_headers(origmsg, newmsg, signkey)
+        # create 'application/octet-stream' encrypted message
+        encmsg = MIMEApplication(
+            self._keymanager.encrypt(origmsg.as_string(unixfrom=False), pubkey,
+                                     sign=signkey),
+            _subtype='octet-stream', _encoder=lambda x: x)
+        encmsg.add_header('content-disposition', 'attachment',
+                          filename='msg.asc')
+        # create meta message
+        metamsg = PGPEncrypted()
+        metamsg.add_header('Content-Disposition', 'attachment')
+        # attach pgp message parts to new message
+        newmsg.attach(metamsg)
+        newmsg.attach(encmsg)
+        return newmsg
+
+
+    def _sign(self, origmsg, signkey):
+        """
+        Create an RFC 3156 compliant PGP signed MIME message using C{signkey}.
+
+        :param origmsg: The original message
+        :type origmsg: email.message.Message
+        :param signkey: The private key used to sign the message.
+        :type signkey: leap.common.keymanager.openpgp.OpenPGPKey
+        :return: The signed message.
+        :rtype: MultipartSigned
+        """
+        # create new multipart/signed message
+        newmsg = MultipartSigned('application/pgp-signature', 'pgp-sha512')
+        # move (almost) all headers from original message to the new message
+        self._fix_headers(origmsg, newmsg, signkey)
+        # apply base64 content-transfer-encoding
+        encode_base64_rec(origmsg)
+        # get message text with headers and replace \n for \r\n
+        fp = StringIO()
+        g = RFC3156CompliantGenerator(
+            fp, mangle_from_=False, maxheaderlen=76)
+        g.flatten(origmsg)
+        msgtext = re.sub('\r?\n', '\r\n', fp.getvalue())
+        # make sure signed message ends with \r\n as per OpenPGP stantard.
+        if origmsg.is_multipart():
+            if not msgtext.endswith("\r\n"):
+                msgtext += "\r\n"
+        # calculate signature
+        signature = self._keymanager.sign(msgtext, signkey, digest_algo='SHA512',
+                                          clearsign=False, detach=True, binary=False)
+        sigmsg = PGPSignature(signature)
+        # attach original message and signature to new message
+        newmsg.attach(origmsg)
+        newmsg.attach(sigmsg)
+        return newmsg
+
+
+    def _fix_headers(self, origmsg, newmsg, signkey):
+        """
+        Move some headers from C{origmsg} to C{newmsg}, delete unwanted
+        headers from C{origmsg} and add new headers to C{newms}.
+
+        Outgoing messages are either encrypted and signed or just signed
+        before being sent. Because of that, they are packed inside new
+        messages and some manipulation has to be made on their headers.
+
+        Allowed headers for passing through:
+
+            - From
+            - Date
+            - To
+            - Subject
+            - Reply-To
+            - References
+            - In-Reply-To
+            - Cc
+
+        Headers to be added:
+
+            - Message-ID (i.e. should not use origmsg's Message-Id)
+            - Received (this is added automatically by twisted smtp API)
+            - OpenPGP (see #4447)
+
+        Headers to be deleted:
+
+            - User-Agent
+
+        :param origmsg: The original message.
+        :type origmsg: email.message.Message
+        :param newmsg: The new message being created.
+        :type newmsg: email.message.Message
+        :param signkey: The key used to sign C{newmsg}
+        :type signkey: OpenPGPKey
+        """
+        # move headers from origmsg to newmsg
+        headers = origmsg.items()
+        passthrough = [
+            'from', 'date', 'to', 'subject', 'reply-to', 'references',
+            'in-reply-to', 'cc'
+        ]
+        headers = filter(lambda x: x[0].lower() in passthrough, headers)
+        for hkey, hval in headers:
+            newmsg.add_header(hkey, hval)
+            del (origmsg[hkey])
+        # add a new message-id to newmsg
+        newmsg.add_header('Message-Id', smtp.messageid())
+        # add openpgp header to newmsg
+        username, domain = signkey.address.split('@')
+        newmsg.add_header(
+            'OpenPGP', 'id=%s' % signkey.key_id,
+            url='https://%s/key/%s' % (domain, username),
+            preference='signencrypt')
+        # delete user-agent from origmsg
+        del (origmsg['user-agent'])
diff --git a/mail/src/leap/mail/smtp/__init__.py b/mail/src/leap/mail/smtp/__init__.py
index bbd4064..f740f5e 100644
--- a/mail/src/leap/mail/smtp/__init__.py
+++ b/mail/src/leap/mail/smtp/__init__.py
@@ -22,6 +22,8 @@ import logging
 
 from twisted.internet import reactor
 from twisted.internet.error import CannotListenError
+from twisted.mail import smtp
+from leap.mail.service import OutgoingMail
 
 logger = logging.getLogger(__name__)
 
@@ -59,8 +61,8 @@ def setup_smtp_gateway(port, userid, keymanager, smtp_host, smtp_port,
     :returns: tuple of SMTPFactory, twisted.internet.tcp.Port
     """
     # configure the use of this service with twistd
-    factory = SMTPFactory(userid, keymanager, smtp_host, smtp_port, smtp_cert,
-                          smtp_key, encrypted_only)
+    outgoing_mail = OutgoingMail(str(userid), keymanager, smtp_cert, smtp_key, smtp_host, smtp_port)
+    factory = SMTPFactory(userid, keymanager, encrypted_only, outgoing_mail)
     try:
         tport = reactor.listenTCP(port, factory, interface="localhost")
         signal(proto.SMTP_SERVICE_STARTED, str(port))
diff --git a/mail/src/leap/mail/smtp/gateway.py b/mail/src/leap/mail/smtp/gateway.py
index 13d3bbf..b022091 100644
--- a/mail/src/leap/mail/smtp/gateway.py
+++ b/mail/src/leap/mail/smtp/gateway.py
@@ -31,39 +31,27 @@ The following classes comprise the SMTP gateway service:
 
 
 """
-import re
-from StringIO import StringIO
-from email.Header import Header
-from email.utils import parseaddr
-from email.parser import Parser
-from email.mime.application import MIMEApplication
 
 from zope.interface import implements
-from OpenSSL import SSL
 from twisted.mail import smtp
 from twisted.internet.protocol import ServerFactory
-from twisted.internet import reactor, ssl
-from twisted.internet import defer
-from twisted.internet.threads import deferToThread
 from twisted.python import log
 
-from leap.common.check import leap_assert, leap_assert_type
+from email.Header import Header
+from leap.common.check import leap_assert_type
 from leap.common.events import proto, signal
-from leap.keymanager import KeyManager
 from leap.keymanager.openpgp import OpenPGPKey
 from leap.keymanager.errors import KeyNotFound
-from leap.mail import __version__
+from leap.mail.utils import validate_address
+
 from leap.mail.smtp.rfc3156 import (
-    MultipartSigned,
-    MultipartEncrypted,
-    PGPEncrypted,
-    PGPSignature,
     RFC3156CompliantGenerator,
-    encode_base64_rec,
 )
 
+from leap.mail.service import OutgoingMail
 # replace email generator with a RFC 3156 compliant one.
 from email import generator
+
 generator.Generator = RFC3156CompliantGenerator
 
 
@@ -74,31 +62,6 @@ generator.Generator = RFC3156CompliantGenerator
 LOCAL_FQDN = "bitmask.local"
 
 
-def validate_address(address):
-    """
-    Validate C{address} as defined in RFC 2822.
-
-    :param address: The address to be validated.
-    :type address: str
-
-    @return: A valid address.
-    @rtype: str
-
-    @raise smtp.SMTPBadRcpt: Raised if C{address} is invalid.
-    """
-    leap_assert_type(address, str)
-    # in the following, the address is parsed as described in RFC 2822 and
-    # ('', '') is returned if the parse fails.
-    _, address = parseaddr(address)
-    if address == '':
-        raise smtp.SMTPBadRcpt(address)
-    return address
-
-
-#
-# SMTPFactory
-#
-
 class SMTPHeloLocalhost(smtp.SMTP):
     """
     An SMTP class that ensures a proper FQDN
@@ -119,45 +82,26 @@ class SMTPFactory(ServerFactory):
     """
     domain = LOCAL_FQDN
 
-    def __init__(self, userid, keymanager, host, port, cert, key,
-                 encrypted_only):
+    def __init__(self, userid, keymanager, encrypted_only, outgoing_mail):
         """
         Initialize the SMTP factory.
 
         :param userid: The user currently logged in
         :type userid: unicode
-        :param keymanager: A KeyManager for retrieving recipient's keys.
-        :type keymanager: leap.common.keymanager.KeyManager
-        :param host: The hostname of the remote SMTP server.
-        :type host: str
-        :param port: The port of the remote SMTP server.
-        :type port: int
-        :param cert: The client certificate for authentication.
-        :type cert: str
-        :param key: The client key for authentication.
-        :type key: str
+        :param keymanager: A Key Manager from where to get recipients' public
+                           keys.
         :param encrypted_only: Whether the SMTP gateway should send unencrypted
                                mail or not.
         :type encrypted_only: bool
+        :param outgoing_mail: The outgoing mail to send the message
+        :type outgoing_mail: leap.mail.service.OutgoingMail
         """
-        # assert params
-        leap_assert_type(keymanager, KeyManager)
-        leap_assert_type(host, str)
-        leap_assert(host != '')
-        leap_assert_type(port, int)
-        leap_assert(port is not 0)
-        leap_assert_type(cert, unicode)
-        leap_assert(cert != '')
-        leap_assert_type(key, unicode)
-        leap_assert(key != '')
+
         leap_assert_type(encrypted_only, bool)
         # and store them
         self._userid = userid
         self._km = keymanager
-        self._host = host
-        self._port = port
-        self._cert = cert
-        self._key = key
+        self._outgoing_mail = outgoing_mail
         self._encrypted_only = encrypted_only
 
     def buildProtocol(self, addr):
@@ -170,9 +114,7 @@ class SMTPFactory(ServerFactory):
         @return: The protocol.
         @rtype: SMTPDelivery
         """
-        smtpProtocol = SMTPHeloLocalhost(SMTPDelivery(
-            self._userid, self._km, self._host, self._port, self._cert,
-            self._key, self._encrypted_only))
+        smtpProtocol = SMTPHeloLocalhost(SMTPDelivery(self._userid, self._km, self._encrypted_only, self._outgoing_mail))
         smtpProtocol.factory = self
         return smtpProtocol
 
@@ -188,33 +130,23 @@ class SMTPDelivery(object):
 
     implements(smtp.IMessageDelivery)
 
-    def __init__(self, userid, keymanager, host, port, cert, key,
-                 encrypted_only):
+    def __init__(self, userid, keymanager, encrypted_only, outgoing_mail):
         """
         Initialize the SMTP delivery object.
 
         :param userid: The user currently logged in
         :type userid: unicode
-        :param keymanager: A KeyManager for retrieving recipient's keys.
-        :type keymanager: leap.common.keymanager.KeyManager
-        :param host: The hostname of the remote SMTP server.
-        :type host: str
-        :param port: The port of the remote SMTP server.
-        :type port: int
-        :param cert: The client certificate for authentication.
-        :type cert: str
-        :param key: The client key for authentication.
-        :type key: str
+        :param keymanager: A Key Manager from where to get recipients' public
+                           keys.
         :param encrypted_only: Whether the SMTP gateway should send unencrypted
                                mail or not.
         :type encrypted_only: bool
+        :param outgoing_mail: The outgoing mail to send the message
+        :type outgoing_mail: leap.mail.service.OutgoingMail
         """
         self._userid = userid
+        self._outgoing_mail = outgoing_mail
         self._km = keymanager
-        self._host = host
-        self._port = port
-        self._cert = cert
-        self._key = key
         self._encrypted_only = encrypted_only
         self._origin = None
 
@@ -280,9 +212,7 @@ class SMTPDelivery(object):
                     "encrypted_only' is set to False).")
             signal(
                 proto.SMTP_RECIPIENT_ACCEPTED_UNENCRYPTED, user.dest.addrstr)
-        return lambda: EncryptedMessage(
-            self._origin, user, self._km, self._host, self._port, self._cert,
-            self._key)
+        return lambda: EncryptedMessage(user, self._outgoing_mail)
 
     def validateFrom(self, helo, origin):
         """
@@ -314,19 +244,6 @@ class SMTPDelivery(object):
 # EncryptedMessage
 #
 
-class SSLContextFactory(ssl.ClientContextFactory):
-    def __init__(self, cert, key):
-        self.cert = cert
-        self.key = key
-
-    def getContext(self):
-        self.method = SSL.TLSv1_METHOD  # SSLv23_METHOD
-        ctx = ssl.ClientContextFactory.getContext(self)
-        ctx.use_certificate_file(self.cert)
-        ctx.use_privatekey_file(self.key)
-        return ctx
-
-
 class EncryptedMessage(object):
     """
     Receive plaintext from client, encrypt it and send message to a
@@ -334,44 +251,21 @@ class EncryptedMessage(object):
     """
     implements(smtp.IMessage)
 
-    FOOTER_STRING = "I prefer encrypted email"
-
-    def __init__(self, fromAddress, user, keymanager, host, port, cert, key):
+    def __init__(self, user, outgoing_mail):
         """
         Initialize the encrypted message.
 
-        :param fromAddress: The address of the sender.
-        :type fromAddress: twisted.mail.smtp.Address
         :param user: The recipient of this message.
         :type user: twisted.mail.smtp.User
-        :param keymanager: A KeyManager for retrieving recipient's keys.
-        :type keymanager: leap.common.keymanager.KeyManager
-        :param host: The hostname of the remote SMTP server.
-        :type host: str
-        :param port: The port of the remote SMTP server.
-        :type port: int
-        :param cert: The client certificate for authentication.
-        :type cert: str
-        :param key: The client key for authentication.
-        :type key: str
+        :param outgoing_mail: The outgoing mail to send the message
+        :type outgoing_mail: leap.mail.service.OutgoingMail
         """
         # assert params
         leap_assert_type(user, smtp.User)
-        leap_assert_type(keymanager, KeyManager)
-        # and store them
-        self._fromAddress = fromAddress
-        self._user = user
-        self._km = keymanager
-        self._host = host
-        self._port = port
-        self._cert = cert
-        self._key = key
-        # initialize list for message's lines
-        self.lines = []
 
-    #
-    # methods from smtp.IMessage
-    #
+        self._user = user
+        self._lines = []
+        self._outgoing_mail = outgoing_mail
 
     def lineReceived(self, line):
         """
@@ -380,7 +274,7 @@ class EncryptedMessage(object):
         :param line: The received line.
         :type line: str
         """
-        self.lines.append(line)
+        self._lines.append(line)
 
     def eomReceived(self):
         """
@@ -391,10 +285,10 @@ class EncryptedMessage(object):
         :returns: a deferred
         """
         log.msg("Message data complete.")
-        self.lines.append('')  # add a trailing newline
-        d = deferToThread(self._maybe_encrypt_and_sign)
-        d.addCallbacks(self.sendMessage, self.skipNoKeyErrBack)
-        return d
+        self._lines.append('')  # add a trailing newline
+        raw_mail = '\r\n'.join(self._lines)
+
+        return self._outgoing_mail.send_message(raw_mail, self._user)
 
     def connectionLost(self):
         """
@@ -404,290 +298,4 @@ class EncryptedMessage(object):
         log.err()
         signal(proto.SMTP_CONNECTION_LOST, self._user.dest.addrstr)
         # unexpected loss of connection; don't save
-        self.lines = []
-
-    # ends IMessage implementation
-
-    def skipNoKeyErrBack(self, failure):
-        """
-        Errback that ignores a KeyNotFound
-
-        :param failure: the failure
-        :type Failure: Failure
-        """
-        err = failure.value
-        if failure.check(KeyNotFound):
-            pass
-        else:
-            raise err
-
-    def parseMessage(self):
-        """
-        Separate message headers from body.
-        """
-        parser = Parser()
-        return parser.parsestr('\r\n'.join(self.lines))
-
-    def sendQueued(self, r):
-        """
-        Callback for the queued message.
-
-        :param r: The result from the last previous callback in the chain.
-        :type r: anything
-        """
-        log.msg(r)
-
-    def sendSuccess(self, r):
-        """
-        Callback for a successful send.
-
-        :param r: The result from the last previous callback in the chain.
-        :type r: anything
-        """
-        log.msg(r)
-        signal(proto.SMTP_SEND_MESSAGE_SUCCESS, self._user.dest.addrstr)
-
-    def sendError(self, failure):
-        """
-        Callback for an unsuccessfull send.
-
-        :param e: The result from the last errback.
-        :type e: anything
-        """
-        signal(proto.SMTP_SEND_MESSAGE_ERROR, self._user.dest.addrstr)
-        err = failure.value
-        log.err(err)
-        raise err
-
-    def sendMessage(self, *args):
-        """
-        Sends the message.
-
-        :return: A deferred with callback and errback for
-                 this #message send.
-        :rtype: twisted.internet.defer.Deferred
-        """
-        d = deferToThread(self._route_msg)
-        d.addCallbacks(self.sendQueued, self.sendError)
-        return d
-
-    def _route_msg(self):
-        """
-        Sends the msg using the ESMTPSenderFactory.
-        """
-        log.msg("Connecting to SMTP server %s:%s" % (self._host, self._port))
-        msg = self._msg.as_string(False)
-
-        # we construct a defer to pass to the ESMTPSenderFactory
-        d = defer.Deferred()
-        d.addCallbacks(self.sendSuccess, self.sendError)
-        # we don't pass an ssl context factory to the ESMTPSenderFactory
-        # because ssl will be handled by reactor.connectSSL() below.
-        factory = smtp.ESMTPSenderFactory(
-            "",  # username is blank because server does not use auth.
-            "",  # password is blank because server does not use auth.
-            self._fromAddress.addrstr,
-            self._user.dest.addrstr,
-            StringIO(msg),
-            d,
-            heloFallback=True,
-            requireAuthentication=False,
-            requireTransportSecurity=True)
-        factory.domain = __version__
-        signal(proto.SMTP_SEND_MESSAGE_START, self._user.dest.addrstr)
-        reactor.connectSSL(
-            self._host, self._port, factory,
-            contextFactory=SSLContextFactory(self._cert, self._key))
-
-    #
-    # encryption methods
-    #
-
-    def _encrypt_and_sign(self, pubkey, signkey):
-        """
-        Create an RFC 3156 compliang PGP encrypted and signed message using
-        C{pubkey} to encrypt and C{signkey} to sign.
-
-        :param pubkey: The public key used to encrypt the message.
-        :type pubkey: OpenPGPKey
-        :param signkey: The private key used to sign the message.
-        :type signkey: OpenPGPKey
-        """
-        # create new multipart/encrypted message with 'pgp-encrypted' protocol
-        newmsg = MultipartEncrypted('application/pgp-encrypted')
-        # move (almost) all headers from original message to the new message
-        self._fix_headers(self._origmsg, newmsg, signkey)
-        # create 'application/octet-stream' encrypted message
-        encmsg = MIMEApplication(
-            self._km.encrypt(self._origmsg.as_string(unixfrom=False), pubkey,
-                             sign=signkey),
-            _subtype='octet-stream', _encoder=lambda x: x)
-        encmsg.add_header('content-disposition', 'attachment',
-                          filename='msg.asc')
-        # create meta message
-        metamsg = PGPEncrypted()
-        metamsg.add_header('Content-Disposition', 'attachment')
-        # attach pgp message parts to new message
-        newmsg.attach(metamsg)
-        newmsg.attach(encmsg)
-        self._msg = newmsg
-
-    def _sign(self, signkey):
-        """
-        Create an RFC 3156 compliant PGP signed MIME message using C{signkey}.
-
-        :param signkey: The private key used to sign the message.
-        :type signkey: leap.common.keymanager.openpgp.OpenPGPKey
-        """
-        # create new multipart/signed message
-        newmsg = MultipartSigned('application/pgp-signature', 'pgp-sha512')
-        # move (almost) all headers from original message to the new message
-        self._fix_headers(self._origmsg, newmsg, signkey)
-        # apply base64 content-transfer-encoding
-        encode_base64_rec(self._origmsg)
-        # get message text with headers and replace \n for \r\n
-        fp = StringIO()
-        g = RFC3156CompliantGenerator(
-            fp, mangle_from_=False, maxheaderlen=76)
-        g.flatten(self._origmsg)
-        msgtext = re.sub('\r?\n', '\r\n', fp.getvalue())
-        # make sure signed message ends with \r\n as per OpenPGP stantard.
-        if self._origmsg.is_multipart():
-            if not msgtext.endswith("\r\n"):
-                msgtext += "\r\n"
-        # calculate signature
-        signature = self._km.sign(msgtext, signkey, digest_algo='SHA512',
-                                  clearsign=False, detach=True, binary=False)
-        sigmsg = PGPSignature(signature)
-        # attach original message and signature to new message
-        newmsg.attach(self._origmsg)
-        newmsg.attach(sigmsg)
-        self._msg = newmsg
-
-    def _maybe_encrypt_and_sign(self):
-        """
-        Attempt to encrypt and sign the outgoing message.
-
-        The behaviour of this method depends on:
-
-            1. the original message's content-type, and
-            2. the availability of the recipient's public key.
-
-        If the original message's content-type is "multipart/encrypted", then
-        the original message is not altered. For any other content-type, the
-        method attempts to fetch the recipient's public key. If the
-        recipient's public key is available, the message is encrypted and
-        signed; otherwise it is only signed.
-
-        Note that, if the C{encrypted_only} configuration is set to True and
-        the recipient's public key is not available, then the recipient
-        address would have been rejected in SMTPDelivery.validateTo().
-
-        The following table summarizes the overall behaviour of the gateway:
-
-        +---------------------------------------------------+----------------+
-        | content-type        | rcpt pubkey | enforce encr. | action         |
-        +---------------------+-------------+---------------+----------------+
-        | multipart/encrypted | any         | any           | pass           |
-        | other               | available   | any           | encrypt + sign |
-        | other               | unavailable | yes           | reject         |
-        | other               | unavailable | no            | sign           |
-        +---------------------+-------------+---------------+----------------+
-        """
-        # pass if the original message's content-type is "multipart/encrypted"
-        self._origmsg = self.parseMessage()
-        if self._origmsg.get_content_type() == 'multipart/encrypted':
-            self._msg = self._origmsg
-            return
-
-        from_address = validate_address(self._fromAddress.addrstr)
-        username, domain = from_address.split('@')
-
-        # add a nice footer to the outgoing message
-        if self._origmsg.get_content_type() == 'text/plain':
-            self.lines.append('--')
-            self.lines.append('%s - https://%s/key/%s' %
-                              (self.FOOTER_STRING, domain, username))
-            self.lines.append('')
-
-        self._origmsg = self.parseMessage()
-
-        # get sender and recipient data
-        signkey = self._km.get_key(from_address, OpenPGPKey, private=True)
-        log.msg("Will sign the message with %s." % signkey.fingerprint)
-        to_address = validate_address(self._user.dest.addrstr)
-        try:
-            # try to get the recipient pubkey
-            pubkey = self._km.get_key(to_address, OpenPGPKey)
-            log.msg("Will encrypt the message to %s." % pubkey.fingerprint)
-            signal(proto.SMTP_START_ENCRYPT_AND_SIGN,
-                   "%s,%s" % (self._fromAddress.addrstr, to_address))
-            self._encrypt_and_sign(pubkey, signkey)
-            signal(proto.SMTP_END_ENCRYPT_AND_SIGN,
-                   "%s,%s" % (self._fromAddress.addrstr, to_address))
-        except KeyNotFound:
-            # at this point we _can_ send unencrypted mail, because if the
-            # configuration said the opposite the address would have been
-            # rejected in SMTPDelivery.validateTo().
-            log.msg('Will send unencrypted message to %s.' % to_address)
-            signal(proto.SMTP_START_SIGN, self._fromAddress.addrstr)
-            self._sign(signkey)
-            signal(proto.SMTP_END_SIGN, self._fromAddress.addrstr)
-
-    def _fix_headers(self, origmsg, newmsg, signkey):
-        """
-        Move some headers from C{origmsg} to C{newmsg}, delete unwanted
-        headers from C{origmsg} and add new headers to C{newms}.
-
-        Outgoing messages are either encrypted and signed or just signed
-        before being sent. Because of that, they are packed inside new
-        messages and some manipulation has to be made on their headers.
-
-        Allowed headers for passing through:
-
-            - From
-            - Date
-            - To
-            - Subject
-            - Reply-To
-            - References
-            - In-Reply-To
-            - Cc
-
-        Headers to be added:
-
-            - Message-ID (i.e. should not use origmsg's Message-Id)
-            - Received (this is added automatically by twisted smtp API)
-            - OpenPGP (see #4447)
-
-        Headers to be deleted:
-
-            - User-Agent
-
-        :param origmsg: The original message.
-        :type origmsg: email.message.Message
-        :param newmsg: The new message being created.
-        :type newmsg: email.message.Message
-        :param signkey: The key used to sign C{newmsg}
-        :type signkey: OpenPGPKey
-        """
-        # move headers from origmsg to newmsg
-        headers = origmsg.items()
-        passthrough = [
-            'from', 'date', 'to', 'subject', 'reply-to', 'references',
-            'in-reply-to', 'cc'
-        ]
-        headers = filter(lambda x: x[0].lower() in passthrough, headers)
-        for hkey, hval in headers:
-            newmsg.add_header(hkey, hval)
-            del(origmsg[hkey])
-        # add a new message-id to newmsg
-        newmsg.add_header('Message-Id', smtp.messageid())
-        # add openpgp header to newmsg
-        username, domain = signkey.address.split('@')
-        newmsg.add_header(
-            'OpenPGP', 'id=%s' % signkey.key_id,
-            url='https://%s/key/%s' % (domain, username),
-            preference='signencrypt')
-        # delete user-agent from origmsg
-        del(origmsg['user-agent'])
+        self._lines = []
diff --git a/mail/src/leap/mail/smtp/tests/__init__.py b/mail/src/leap/mail/smtp/tests/__init__.py
new file mode 100644
index 0000000..e69de29
--- /dev/null
+++ b/mail/src/leap/mail/smtp/tests/__init__.py
diff --git a/mail/src/leap/mail/smtp/tests/test_gateway.py b/mail/src/leap/mail/smtp/tests/test_gateway.py
index 3635a9f..aeace4a 100644
--- a/mail/src/leap/mail/smtp/tests/test_gateway.py
+++ b/mail/src/leap/mail/smtp/tests/test_gateway.py
@@ -20,17 +20,14 @@
 SMTP gateway tests.
 """
 
-
 import re
 from datetime import datetime
+
 from twisted.test import proto_helpers
-from twisted.mail.smtp import User, Address
 
 from mock import Mock
-
 from leap.mail.smtp.gateway import (
-    SMTPFactory,
-    EncryptedMessage,
+    SMTPFactory
 )
 from leap.mail.tests import (
     TestCaseWithKeyManager,
@@ -39,6 +36,7 @@ from leap.mail.tests import (
 )
 from leap.keymanager import openpgp
 
+
 # some regexps
 IP_REGEX = "(([0-9]|[1-9][0-9]|1[0-9]{2}|2[0-4][0-9]|25[0-5])\.){3}" + \
     "([0-9]|[1-9][0-9]|1[0-9]{2}|2[0-4][0-9]|25[0-5])"
@@ -71,20 +69,6 @@ class TestSmtpGateway(TestCaseWithKeyManager):
                                            % (string, pattern))
             raise self.failureException(msg)
 
-    def test_openpgp_encrypt_decrypt(self):
-        "Test if openpgp can encrypt and decrypt."
-        text = "simple raw text"
-        pubkey = self._km.get_key(
-            ADDRESS, openpgp.OpenPGPKey, private=False)
-        encrypted = self._km.encrypt(text, pubkey)
-        self.assertNotEqual(
-            text, encrypted, "Ciphertext is equal to plaintext.")
-        privkey = self._km.get_key(
-            ADDRESS, openpgp.OpenPGPKey, private=True)
-        decrypted = self._km.decrypt(encrypted, privkey)
-        self.assertEqual(text, decrypted,
-                         "Decrypted text differs from plaintext.")
-
     def test_gateway_accepts_valid_email(self):
         """
         Test if SMTP server responds correctly for valid interaction.
@@ -102,10 +86,8 @@ class TestSmtpGateway(TestCaseWithKeyManager):
         # method...
         proto = SMTPFactory(
             u'anotheruser@leap.se',
-            self._km, self._config['host'],
-            self._config['port'],
-            self._config['cert'], self._config['key'],
-            self._config['encrypted_only']).buildProtocol(('127.0.0.1', 0))
+            self._km,
+            self._config['encrypted_only'], outgoing_mail=Mock()).buildProtocol(('127.0.0.1', 0))
         # snip...
         transport = proto_helpers.StringTransport()
         proto.makeConnection(transport)
@@ -116,151 +98,6 @@ class TestSmtpGateway(TestCaseWithKeyManager):
                              'Did not get expected answer from gateway.')
         proto.setTimeout(None)
 
-    def test_message_encrypt(self):
-        """
-        Test if message gets encrypted to destination email.
-        """
-        proto = SMTPFactory(
-            u'anotheruser@leap.se',
-            self._km, self._config['host'],
-            self._config['port'],
-            self._config['cert'], self._config['key'],
-            self._config['encrypted_only']).buildProtocol(('127.0.0.1', 0))
-        fromAddr = Address(ADDRESS_2)
-        dest = User(ADDRESS, 'gateway.leap.se', proto, ADDRESS)
-        m = EncryptedMessage(
-            fromAddr, dest, self._km, self._config['host'],
-            self._config['port'], self._config['cert'], self._config['key'])
-        for line in self.EMAIL_DATA[4:12]:
-            m.lineReceived(line)
-        # m.eomReceived()  # this includes a defer, so we avoid calling it here
-        m.lines.append('')  # add a trailing newline
-        # we need to call the following explicitelly because it was deferred
-        # inside the previous method
-        m._maybe_encrypt_and_sign()
-        # assert structure of encrypted message
-        self.assertTrue('Content-Type' in m._msg)
-        self.assertEqual('multipart/encrypted', m._msg.get_content_type())
-        self.assertEqual('application/pgp-encrypted',
-                         m._msg.get_param('protocol'))
-        self.assertEqual(2, len(m._msg.get_payload()))
-        self.assertEqual('application/pgp-encrypted',
-                         m._msg.get_payload(0).get_content_type())
-        self.assertEqual('application/octet-stream',
-                         m._msg.get_payload(1).get_content_type())
-        privkey = self._km.get_key(
-            ADDRESS, openpgp.OpenPGPKey, private=True)
-        decrypted = self._km.decrypt(
-            m._msg.get_payload(1).get_payload(), privkey)
-        self.assertEqual(
-            '\n' + '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n\r\n--\r\n' +
-            'I prefer encrypted email - https://leap.se/key/anotheruser\r\n',
-            decrypted,
-            'Decrypted text differs from plaintext.')
-
-    def test_message_encrypt_sign(self):
-        """
-        Test if message gets encrypted to destination email and signed with
-        sender key.
-        """
-        proto = SMTPFactory(
-            u'anotheruser@leap.se',
-            self._km, self._config['host'],
-            self._config['port'],
-            self._config['cert'], self._config['key'],
-            self._config['encrypted_only']).buildProtocol(('127.0.0.1', 0))
-        user = User(ADDRESS, 'gateway.leap.se', proto, ADDRESS)
-        fromAddr = Address(ADDRESS_2)
-        m = EncryptedMessage(
-            fromAddr, user, self._km, self._config['host'],
-            self._config['port'], self._config['cert'], self._config['key'])
-        for line in self.EMAIL_DATA[4:12]:
-            m.lineReceived(line)
-        # trigger encryption and signing
-        # m.eomReceived()  # this includes a defer, so we avoid calling it here
-        m.lines.append('')  # add a trailing newline
-        # we need to call the following explicitelly because it was deferred
-        # inside the previous method
-        m._maybe_encrypt_and_sign()
-        # assert structure of encrypted message
-        self.assertTrue('Content-Type' in m._msg)
-        self.assertEqual('multipart/encrypted', m._msg.get_content_type())
-        self.assertEqual('application/pgp-encrypted',
-                         m._msg.get_param('protocol'))
-        self.assertEqual(2, len(m._msg.get_payload()))
-        self.assertEqual('application/pgp-encrypted',
-                         m._msg.get_payload(0).get_content_type())
-        self.assertEqual('application/octet-stream',
-                         m._msg.get_payload(1).get_content_type())
-        # decrypt and verify
-        privkey = self._km.get_key(
-            ADDRESS, openpgp.OpenPGPKey, private=True)
-        pubkey = self._km.get_key(ADDRESS_2, openpgp.OpenPGPKey)
-        decrypted = self._km.decrypt(
-            m._msg.get_payload(1).get_payload(), privkey, verify=pubkey)
-        self.assertEqual(
-            '\n' + '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n\r\n--\r\n' +
-            'I prefer encrypted email - https://leap.se/key/anotheruser\r\n',
-            decrypted,
-            'Decrypted text differs from plaintext.')
-
-    def test_message_sign(self):
-        """
-        Test if message is signed with sender key.
-        """
-        # mock the key fetching
-        self._km.fetch_keys_from_server = Mock(return_value=[])
-        proto = SMTPFactory(
-            u'anotheruser@leap.se',
-            self._km, self._config['host'],
-            self._config['port'],
-            self._config['cert'], self._config['key'],
-            self._config['encrypted_only']).buildProtocol(('127.0.0.1', 0))
-        user = User('ihavenopubkey@nonleap.se',
-                    'gateway.leap.se', proto, ADDRESS)
-        fromAddr = Address(ADDRESS_2)
-        m = EncryptedMessage(
-            fromAddr, user, self._km, self._config['host'],
-            self._config['port'], self._config['cert'], self._config['key'])
-        for line in self.EMAIL_DATA[4:12]:
-            m.lineReceived(line)
-        # trigger signing
-        # m.eomReceived()  # this includes a defer, so we avoid calling it here
-        m.lines.append('')  # add a trailing newline
-        # we need to call the following explicitelly because it was deferred
-        # inside the previous method
-        m._maybe_encrypt_and_sign()
-        # assert structure of signed message
-        self.assertTrue('Content-Type' in m._msg)
-        self.assertEqual('multipart/signed', m._msg.get_content_type())
-        self.assertEqual('application/pgp-signature',
-                         m._msg.get_param('protocol'))
-        self.assertEqual('pgp-sha512', m._msg.get_param('micalg'))
-        # assert content of message
-        self.assertEqual(
-            '\r\n'.join(self.EMAIL_DATA[9:13]) + '\r\n--\r\n' +
-            'I prefer encrypted email - https://leap.se/key/anotheruser\r\n',
-            m._msg.get_payload(0).get_payload(decode=True))
-        # assert content of signature
-        self.assertTrue(
-            m._msg.get_payload(1).get_payload().startswith(
-                '-----BEGIN PGP SIGNATURE-----\n'),
-            'Message does not start with signature header.')
-        self.assertTrue(
-            m._msg.get_payload(1).get_payload().endswith(
-                '-----END PGP SIGNATURE-----\n'),
-            'Message does not end with signature footer.')
-        # assert signature is valid
-        pubkey = self._km.get_key(ADDRESS_2, openpgp.OpenPGPKey)
-        # replace EOL before verifying (according to rfc3156)
-        signed_text = re.sub('\r?\n', '\r\n',
-                             m._msg.get_payload(0).as_string())
-        self.assertTrue(
-            self._km.verify(signed_text,
-                            pubkey,
-                            detached_sig=m._msg.get_payload(1).get_payload()),
-            'Signature could not be verified.')
-
     def test_missing_key_rejects_address(self):
         """
         Test if server rejects to send unencrypted when 'encrypted_only' is
@@ -276,10 +113,8 @@ class TestSmtpGateway(TestCaseWithKeyManager):
         # prepare the SMTP factory
         proto = SMTPFactory(
             u'anotheruser@leap.se',
-            self._km, self._config['host'],
-            self._config['port'],
-            self._config['cert'], self._config['key'],
-            self._config['encrypted_only']).buildProtocol(('127.0.0.1', 0))
+            self._km,
+            self._config['encrypted_only'], outgoing_mail=Mock()).buildProtocol(('127.0.0.1', 0))
         transport = proto_helpers.StringTransport()
         proto.makeConnection(transport)
         proto.lineReceived(self.EMAIL_DATA[0] + '\r\n')
@@ -307,10 +142,8 @@ class TestSmtpGateway(TestCaseWithKeyManager):
         # prepare the SMTP factory with encrypted only equal to false
         proto = SMTPFactory(
             u'anotheruser@leap.se',
-            self._km, self._config['host'],
-            self._config['port'],
-            self._config['cert'], self._config['key'],
-            False).buildProtocol(('127.0.0.1', 0))
+            self._km,
+            False, outgoing_mail=Mock()).buildProtocol(('127.0.0.1', 0))
         transport = proto_helpers.StringTransport()
         proto.makeConnection(transport)
         proto.lineReceived(self.EMAIL_DATA[0] + '\r\n')
diff --git a/mail/src/leap/mail/tests/test_service.py b/mail/src/leap/mail/tests/test_service.py
new file mode 100644
index 0000000..f0a807d
--- /dev/null
+++ b/mail/src/leap/mail/tests/test_service.py
@@ -0,0 +1,185 @@
+# -*- coding: utf-8 -*-
+# test_gateway.py
+# Copyright (C) 2013 LEAP
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program. If not, see <http://www.gnu.org/licenses/>.
+
+
+"""
+SMTP gateway tests.
+"""
+
+import re
+from datetime import datetime
+from twisted.mail.smtp import User, Address
+
+from mock import Mock
+
+from leap.mail.smtp.gateway import SMTPFactory
+from leap.mail.service import OutgoingMail
+from leap.mail.tests import (
+    TestCaseWithKeyManager,
+    ADDRESS,
+    ADDRESS_2,
+)
+from leap.keymanager import openpgp
+
+
+class TestOutgoingMail(TestCaseWithKeyManager):
+    EMAIL_DATA = ['HELO gateway.leap.se',
+                  'MAIL FROM: <%s>' % ADDRESS_2,
+                  'RCPT TO: <%s>' % ADDRESS,
+                  'DATA',
+                  'From: User <%s>' % ADDRESS_2,
+                  'To: Leap <%s>' % ADDRESS,
+                  'Date: ' + datetime.now().strftime('%c'),
+                  'Subject: test message',
+                  '',
+                  'This is a secret message.',
+                  'Yours,',
+                  'A.',
+                  '',
+                  '.',
+                  'QUIT']
+
+    def setUp(self):
+        TestCaseWithKeyManager.setUp(self)
+        self.lines = [line for line in self.EMAIL_DATA[4:12]]
+        self.lines.append('')  # add a trailing newline
+        self.raw = '\r\n'.join(self.lines)
+        self.fromAddr = ADDRESS_2
+        self.outgoing_mail = OutgoingMail(self.fromAddr, self._km, self._config['cert'], self._config['key'],
+                                        self._config['host'], self._config['port'])
+        self.proto = SMTPFactory(
+            u'anotheruser@leap.se',
+            self._km,
+            self._config['encrypted_only'],
+            self.outgoing_mail).buildProtocol(('127.0.0.1', 0))
+        self.dest = User(ADDRESS, 'gateway.leap.se', self.proto, ADDRESS)
+
+    def test_openpgp_encrypt_decrypt(self):
+        "Test if openpgp can encrypt and decrypt."
+        text = "simple raw text"
+        pubkey = self._km.get_key(
+            ADDRESS, openpgp.OpenPGPKey, private=False)
+        encrypted = self._km.encrypt(text, pubkey)
+        self.assertNotEqual(
+            text, encrypted, "Ciphertext is equal to plaintext.")
+        privkey = self._km.get_key(
+            ADDRESS, openpgp.OpenPGPKey, private=True)
+        decrypted = self._km.decrypt(encrypted, privkey)
+        self.assertEqual(text, decrypted,
+                         "Decrypted text differs from plaintext.")
+
+    def test_message_encrypt(self):
+        """
+        Test if message gets encrypted to destination email.
+        """
+
+        message, _ = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
+
+        # assert structure of encrypted message
+        self.assertTrue('Content-Type' in message)
+        self.assertEqual('multipart/encrypted', message.get_content_type())
+        self.assertEqual('application/pgp-encrypted',
+                         message.get_param('protocol'))
+        self.assertEqual(2, len(message.get_payload()))
+        self.assertEqual('application/pgp-encrypted',
+                         message.get_payload(0).get_content_type())
+        self.assertEqual('application/octet-stream',
+                         message.get_payload(1).get_content_type())
+        privkey = self._km.get_key(
+            ADDRESS, openpgp.OpenPGPKey, private=True)
+        decrypted = self._km.decrypt(
+            message.get_payload(1).get_payload(), privkey)
+
+        expected = '\n' + '\r\n'.join(
+            self.EMAIL_DATA[9:12]) + '\r\n\r\n--\r\n' + 'I prefer encrypted email - https://leap.se/key/anotheruser\r\n'
+        self.assertEqual(
+            expected,
+            decrypted,
+            'Decrypted text differs from plaintext.')
+
+    def test_message_encrypt_sign(self):
+        """
+        Test if message gets encrypted to destination email and signed with
+        sender key.
+        """
+        message, _ = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
+
+        # assert structure of encrypted message
+        self.assertTrue('Content-Type' in message)
+        self.assertEqual('multipart/encrypted', message.get_content_type())
+        self.assertEqual('application/pgp-encrypted',
+                         message.get_param('protocol'))
+        self.assertEqual(2, len(message.get_payload()))
+        self.assertEqual('application/pgp-encrypted',
+                         message.get_payload(0).get_content_type())
+        self.assertEqual('application/octet-stream',
+                         message.get_payload(1).get_content_type())
+        # decrypt and verify
+        privkey = self._km.get_key(
+            ADDRESS, openpgp.OpenPGPKey, private=True)
+        pubkey = self._km.get_key(ADDRESS_2, openpgp.OpenPGPKey)
+        decrypted = self._km.decrypt(
+            message.get_payload(1).get_payload(), privkey, verify=pubkey)
+        self.assertEqual(
+            '\n' + '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n\r\n--\r\n' +
+            'I prefer encrypted email - https://leap.se/key/anotheruser\r\n',
+            decrypted,
+            'Decrypted text differs from plaintext.')
+
+    def test_message_sign(self):
+        """
+        Test if message is signed with sender key.
+        """
+        # mock the key fetching
+        self._km.fetch_keys_from_server = Mock(return_value=[])
+        recipient = User('ihavenopubkey@nonleap.se',
+                    'gateway.leap.se', self.proto, ADDRESS)
+        self.outgoing_mail = OutgoingMail(self.fromAddr, self._km, self._config['cert'], self._config['key'],
+                                        self._config['host'], self._config['port'])
+
+        message, _ = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, recipient)
+
+        # assert structure of signed message
+        self.assertTrue('Content-Type' in message)
+        self.assertEqual('multipart/signed', message.get_content_type())
+        self.assertEqual('application/pgp-signature',
+                         message.get_param('protocol'))
+        self.assertEqual('pgp-sha512', message.get_param('micalg'))
+        # assert content of message
+        self.assertEqual(
+            '\r\n'.join(self.EMAIL_DATA[9:13]) + '\r\n--\r\n' +
+            'I prefer encrypted email - https://leap.se/key/anotheruser\r\n',
+            message.get_payload(0).get_payload(decode=True))
+        # assert content of signature
+        self.assertTrue(
+            message.get_payload(1).get_payload().startswith(
+                '-----BEGIN PGP SIGNATURE-----\n'),
+            'Message does not start with signature header.')
+        self.assertTrue(
+            message.get_payload(1).get_payload().endswith(
+                '-----END PGP SIGNATURE-----\n'),
+            'Message does not end with signature footer.')
+        # assert signature is valid
+        pubkey = self._km.get_key(ADDRESS_2, openpgp.OpenPGPKey)
+        # replace EOL before verifying (according to rfc3156)
+        signed_text = re.sub('\r?\n', '\r\n',
+                             message.get_payload(0).as_string())
+        self.assertTrue(
+            self._km.verify(signed_text,
+                            pubkey,
+                            detached_sig=message.get_payload(1).get_payload()),
+            'Signature could not be verified.')
diff --git a/mail/src/leap/mail/utils.py b/mail/src/leap/mail/utils.py
index fed24b3..457097b 100644
--- a/mail/src/leap/mail/utils.py
+++ b/mail/src/leap/mail/utils.py
@@ -17,12 +17,15 @@
 """
 Mail utilities.
 """
+from email.utils import parseaddr
 import json
 import re
 import traceback
 import Queue
 
 from leap.soledad.common.document import SoledadDocument
+from leap.common.check import leap_assert_type
+from twisted.mail import smtp
 
 
 CHARSET_PATTERN = r"""charset=([\w-]+)"""
@@ -224,6 +227,26 @@ def accumulator_queue(fun, lim):
     return _accumulator
 
 
+def validate_address(address):
+    """
+    Validate C{address} as defined in RFC 2822.
+
+    :param address: The address to be validated.
+    :type address: str
+
+    @return: A valid address.
+    @rtype: str
+
+    @raise smtp.SMTPBadRcpt: Raised if C{address} is invalid.
+    """
+    leap_assert_type(address, str)
+    # in the following, the address is parsed as described in RFC 2822 and
+    # ('', '') is returned if the parse fails.
+    _, address = parseaddr(address)
+    if address == '':
+        raise smtp.SMTPBadRcpt(address)
+    return address
+
 #
 # String manipulation
 #