Merge remote-tracking branch 'drebs/feature/4324_prevent-double-encryption-when-relaying-2' into develop

8 files changed, 233 insertions, 265 deletions

diff --git a/changes/bug_4416-change-smtp-relay-to-gateway b/changes/bug_4416-change-smtp-relay-to-gateway
new file mode 100644
index 0000000..08bead7
--- /dev/null
+++ b/changes/bug_4416-change-smtp-relay-to-gateway
@@ -0,0 +1 @@
+  o Change SMTP service name from "relay" to "gateway". Closes #4416.
diff --git a/changes/feature-4324_prevent-double-encryption-when-relaying b/changes/feature-4324_prevent-double-encryption-when-relaying
new file mode 100644
index 0000000..a3d70a9
--- /dev/null
+++ b/changes/feature-4324_prevent-double-encryption-when-relaying
@@ -0,0 +1,2 @@
+  o Prevent already encrypted outgoing messages from being encrypted again.
+    Closes #4324.
diff --git a/src/leap/mail/imap/tests/test_imap.py b/src/leap/mail/imap/tests/test_imap.py
index 3411795..ad11315 100644
--- a/src/leap/mail/imap/tests/test_imap.py
+++ b/src/leap/mail/imap/tests/test_imap.py
@@ -91,7 +91,7 @@ def initialize_soledad(email, gnupg_home, tempdir):
     """
 
     uuid = "foobar-uuid"
-    passphrase = "verysecretpassphrase"
+    passphrase = u"verysecretpassphrase"
     secret_path = os.path.join(tempdir, "secret.gpg")
     local_db_path = os.path.join(tempdir, "soledad.u1db")
     server_url = "http://provider"
@@ -101,6 +101,8 @@ def initialize_soledad(email, gnupg_home, tempdir):
 
         get_doc = Mock(return_value=None)
         put_doc = Mock()
+        lock = Mock(return_value=('atoken', 300))
+        unlock = Mock(return_value=True)
 
         def __call__(self):
             return self
diff --git a/src/leap/mail/smtp/README.rst b/src/leap/mail/smtp/README.rst
index 2b2a118..f625441 100644
--- a/src/leap/mail/smtp/README.rst
+++ b/src/leap/mail/smtp/README.rst
@@ -1,43 +1,23 @@
-Leap SMTP Relay
-===============
+Leap SMTP Gateway
+=================
 
 Outgoing mail workflow:
 
     * LEAP client runs a thin SMTP proxy on the user's device, bound to
       localhost.
-    * User's MUA is configured outgoing SMTP to localhost
-    * When SMTP proxy receives an email from MUA
+    * User's MUA is configured outgoing SMTP to localhost.
+    * When SMTP proxy receives an email from MUA:
         * SMTP proxy queries Key Manager for the user's private key and public
-          keys of all recipients
+          keys of all recipients.
         * Message is signed by sender and encrypted to recipients.
         * If recipient's key is missing, email goes out in cleartext (unless
-          user has configured option to send only encrypted email)
-        * Finally, message is relayed to provider's SMTP relay
-
-
-Dependencies
-------------
-
-Leap SMTP Relay depends on the following python libraries:
-
-  * Twisted 12.3.0 [1]
-  * zope.interface 4.0.3 [2]
-
-[1] http://pypi.python.org/pypi/Twisted/12.3.0
-[2] http://pypi.python.org/pypi/zope.interface/4.0.3
-
-
-How to run
-----------
-
-To launch the SMTP relay, run the following command:
-
-  twistd -y smtprelay.tac
+          user has configured option to send only encrypted email).
+        * Finally, message is gatewayed to provider's SMTP server.
 
 
 Running tests
 -------------
 
-Tests are run using Twisted's Trial API, like this:
+Tests are run using Twisted's Trial API, like this::
 
-  trial leap.email.smtp.tests
+    python setup.py test -s leap.mail.gateway.tests
diff --git a/src/leap/mail/smtp/__init__.py b/src/leap/mail/smtp/__init__.py
index be568b8..d3eb9e8 100644
--- a/src/leap/mail/smtp/__init__.py
+++ b/src/leap/mail/smtp/__init__.py
@@ -16,7 +16,7 @@
 # along with this program. If not, see <http://www.gnu.org/licenses/>.
 
 """
-SMTP relay helper function.
+SMTP gateway helper function.
 """
 import logging
 
@@ -26,15 +26,15 @@ from twisted.internet.error import CannotListenError
 logger = logging.getLogger(__name__)
 
 from leap.common.events import proto, signal
-from leap.mail.smtp.smtprelay import SMTPFactory
+from leap.mail.smtp.gateway import SMTPFactory
 
 
-def setup_smtp_relay(port, userid, keymanager, smtp_host, smtp_port,
+def setup_smtp_gateway(port, userid, keymanager, smtp_host, smtp_port,
                      smtp_cert, smtp_key, encrypted_only):
     """
-    Setup SMTP relay to run with Twisted.
+    Setup SMTP gateway to run with Twisted.
 
-    This function sets up the SMTP relay configuration and the Twisted
+    This function sets up the SMTP gateway configuration and the Twisted
     reactor.
 
     :param port: The port in which to run the server.
@@ -46,48 +46,29 @@ def setup_smtp_relay(port, userid, keymanager, smtp_host, smtp_port,
     :type keymanager: leap.common.keymanager.KeyManager
     :param smtp_host: The hostname of the remote SMTP server.
     :type smtp_host: str
-    :param smtp_port:  The port of the remote SMTP server.
+    :param smtp_port: The port of the remote SMTP server.
     :type smtp_port: int
     :param smtp_cert: The client certificate for authentication.
     :type smtp_cert: str
     :param smtp_key: The client key for authentication.
     :type smtp_key: str
-    :param encrypted_only: Whether the SMTP relay should send unencrypted mail
+    :param encrypted_only: Whether the SMTP gateway should send unencrypted mail
                            or not.
     :type encrypted_only: bool
 
     :returns: tuple of SMTPFactory, twisted.internet.tcp.Port
     """
-    # The configuration for the SMTP relay is a dict with the following
-    # format:
-    #
-    # {
-    #     'host': '<host>',
-    #     'port': <int>,
-    #     'cert': '<cert path>',
-    #     'key': '<key path>',
-    #     'encrypted_only': <True/False>
-    # }
-    config = {
-        'host': smtp_host,
-        'port': smtp_port,
-        'cert': smtp_cert,
-        'key': smtp_key,
-        'encrypted_only': encrypted_only
-    }
-
     # configure the use of this service with twistd
-    factory = SMTPFactory(userid, keymanager, config)
+    factory = SMTPFactory(userid, keymanager, smtp_host, smtp_port, smtp_cert,
+                          smtp_key, encrypted_only)
     try:
-        tport = reactor.listenTCP(port, factory,
-                                  interface="localhost")
-        signal(proto.SMTP_SERVICE_STARTED, str(smtp_port))
+        tport = reactor.listenTCP(port, factory, interface="localhost")
+        signal(proto.SMTP_SERVICE_STARTED, str(port))
         return factory, tport
     except CannotListenError:
         logger.error("STMP Service failed to start: "
-                     "cannot listen in port %s" % (
-                         smtp_port,))
-        signal(proto.SMTP_SERVICE_FAILED_TO_START, str(smtp_port))
+                     "cannot listen in port %s" % port)
+        signal(proto.SMTP_SERVICE_FAILED_TO_START, str(port))
     except Exception as exc:
-        logger.error("Unhandled error while launching smtp relay service")
+        logger.error("Unhandled error while launching smtp gateway service")
         logger.exception(exc)
diff --git a/src/leap/mail/smtp/smtprelay.py b/src/leap/mail/smtp/gateway.py
index 92a9f0e..06405b4 100644
--- a/src/leap/mail/smtp/smtprelay.py
+++ b/src/leap/mail/smtp/gateway.py
@@ -1,5 +1,5 @@
 # -*- coding: utf-8 -*-
-# smtprelay.py
+# gateway.py
 # Copyright (C) 2013 LEAP
 #
 # This program is free software: you can redistribute it and/or modify
@@ -16,9 +16,9 @@
 # along with this program. If not, see <http://www.gnu.org/licenses/>.
 
 """
-LEAP SMTP encrypted relay.
+LEAP SMTP encrypted gateway.
 
-The following classes comprise the SMTP relay service:
+The following classes comprise the SMTP gateway service:
 
     * SMTPFactory - A twisted.internet.protocol.ServerFactory that provides
       the SMTPDelivery protocol.
@@ -68,67 +68,15 @@ generator.Generator = RFC3156CompliantGenerator
 
 
 #
-# Exceptions
-#
-
-class MalformedConfig(Exception):
-    """
-    Raised when the configuration dictionary passed as parameter is malformed.
-    """
-    pass
-
-
-#
 # Helper utilities
 #
 
-HOST_KEY = 'host'
-PORT_KEY = 'port'
-CERT_KEY = 'cert'
-KEY_KEY = 'key'
-ENCRYPTED_ONLY_KEY = 'encrypted_only'
-
-
-def assert_config_structure(config):
-    """
-    Assert that C{config} is a dict with the following structure:
-
-        {
-            HOST_KEY: '<str>',
-            PORT_KEY: <int>,
-            CERT_KEY: '<str>',
-            KEY_KEY: '<str>',
-            ENCRYPTED_ONLY_KEY: <bool>,
-        }
-
-    @param config: The dictionary to check.
-    @type config: dict
-    """
-    # assert smtp config structure is valid
-    leap_assert_type(config, dict)
-    leap_assert(HOST_KEY in config)
-    leap_assert_type(config[HOST_KEY], str)
-    leap_assert(PORT_KEY in config)
-    leap_assert_type(config[PORT_KEY], int)
-    leap_assert(CERT_KEY in config)
-    leap_assert_type(config[CERT_KEY], (str, unicode))
-    leap_assert(KEY_KEY in config)
-    leap_assert_type(config[KEY_KEY], (str, unicode))
-    leap_assert(ENCRYPTED_ONLY_KEY in config)
-    leap_assert_type(config[ENCRYPTED_ONLY_KEY], bool)
-    # assert received params are not empty
-    leap_assert(config[HOST_KEY] != '')
-    leap_assert(config[PORT_KEY] is not 0)
-    leap_assert(config[CERT_KEY] != '')
-    leap_assert(config[KEY_KEY] != '')
-
-
 def validate_address(address):
     """
     Validate C{address} as defined in RFC 2822.
 
-    @param address: The address to be validated.
-    @type address: str
+    :param address: The address to be validated.
+    :type address: str
 
     @return: A valid address.
     @rtype: str
@@ -150,48 +98,63 @@ def validate_address(address):
 
 class SMTPFactory(ServerFactory):
     """
-    Factory for an SMTP server with encrypted relaying capabilities.
+    Factory for an SMTP server with encrypted gatewaying capabilities.
     """
 
-    def __init__(self, userid, keymanager, config):
+    def __init__(self, userid, keymanager, host, port, cert, key,
+                 encrypted_only):
         """
         Initialize the SMTP factory.
 
-        @param keymanager: A KeyManager for retrieving recipient's keys.
-        @type keymanager: leap.common.keymanager.KeyManager
-        @param config: A dictionary with smtp configuration. Should have
-            the following structure:
-                {
-                    HOST_KEY: '<str>',
-                    PORT_KEY: <int>,
-                    CERT_KEY: '<str>',
-                    KEY_KEY: '<str>',
-                    ENCRYPTED_ONLY_KEY: <bool>,
-                }
-        @type config: dict
-        @param userid: The user currently logged in
-        @type userid: unicode
+        :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 encrypted_only: Whether the SMTP gateway should send unencrypted
+                               mail or not.
+        :type encrypted_only: bool
         """
         # assert params
         leap_assert_type(keymanager, KeyManager)
-        assert_config_structure(config)
+        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._config = config
+        self._host = host
+        self._port = port
+        self._cert = cert
+        self._key = key
+        self._encrypted_only = encrypted_only
 
     def buildProtocol(self, addr):
         """
         Return a protocol suitable for the job.
 
-        @param addr: An address, e.g. a TCP (host, port).
-        @type addr:  twisted.internet.interfaces.IAddress
+        :param addr: An address, e.g. a TCP (host, port).
+        :type addr:  twisted.internet.interfaces.IAddress
 
         @return: The protocol.
         @rtype: SMTPDelivery
         """
-        smtpProtocol = smtp.SMTP(SMTPDelivery(self._userid, self._km,
-                                              self._config))
+        smtpProtocol = smtp.SMTP(SMTPDelivery(
+            self._userid, self._km, self._host, self._port, self._cert,
+            self._key, self._encrypted_only))
         smtpProtocol.factory = self
         return smtpProtocol
 
@@ -207,49 +170,53 @@ class SMTPDelivery(object):
 
     implements(smtp.IMessageDelivery)
 
-    def __init__(self, userid, keymanager, config):
+    def __init__(self, userid, keymanager, host, port, cert, key,
+                 encrypted_only):
         """
         Initialize the SMTP delivery object.
 
-        @param keymanager: A KeyManager for retrieving recipient's keys.
-        @type keymanager: leap.common.keymanager.KeyManager
-        @param config: A dictionary with smtp configuration. Should have
-            the following structure:
-                {
-                    HOST_KEY: '<str>',
-                    PORT_KEY: <int>,
-                    CERT_KEY: '<str>',
-                    KEY_KEY: '<str>',
-                    ENCRYPTED_ONLY_KEY: <bool>,
-                }
-        @type config: dict
-        @param userid: The user currently logged in
-        @type userid: unicode
+        :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 encrypted_only: Whether the SMTP gateway should send unencrypted
+                               mail or not.
+        :type encrypted_only: bool
         """
-        # assert params
-        leap_assert_type(keymanager, KeyManager)
-        assert_config_structure(config)
-        # and store them
         self._userid = userid
         self._km = keymanager
-        self._config = config
+        self._userid = userid
+        self._km = keymanager
+        self._host = host
+        self._port = port
+        self._cert = cert
+        self._key = key
+        self._encrypted_only = encrypted_only
         self._origin = None
 
     def receivedHeader(self, helo, origin, recipients):
         """
         Generate the 'Received:' header for a message.
 
-        @param helo: The argument to the HELO command and the client's IP
+        :param helo: The argument to the HELO command and the client's IP
             address.
-        @type helo: (str, str)
-        @param origin: The address the message is from.
-        @type origin: twisted.mail.smtp.Address
-        @param recipients: A list of the addresses for which this message is
+        :type helo: (str, str)
+        :param origin: The address the message is from.
+        :type origin: twisted.mail.smtp.Address
+        :param recipients: A list of the addresses for which this message is
             bound.
-        @type: list of twisted.mail.smtp.User
+        :type: list of twisted.mail.smtp.User
 
         @return: The full "Received" header string.
-        @type: str
+        :type: str
         """
         myHostname, clientIP = helo
         headerValue = "by %s from %s with ESMTP ; %s" % (
@@ -269,8 +236,8 @@ class SMTPDelivery(object):
         In the end, it returns an encrypted message object that is able to
         send itself to the C{user}'s address.
 
-        @param user: The user whose address we wish to validate.
-        @type: twisted.mail.smtp.User
+        :param user: The user whose address we wish to validate.
+        :type: twisted.mail.smtp.User
 
         @return: A Deferred which becomes, or a callable which takes no
             arguments and returns an object implementing IMessage. This will
@@ -284,12 +251,13 @@ class SMTPDelivery(object):
         # try to find recipient's public key
         try:
             address = validate_address(user.dest.addrstr)
-            pubkey = self._km.get_key(address, OpenPGPKey)
+            # verify if recipient key is available in keyring
+            self._km.get_key(address, OpenPGPKey)  # might raise KeyNotFound
             log.msg("Accepting mail for %s..." % user.dest.addrstr)
             signal(proto.SMTP_RECIPIENT_ACCEPTED_ENCRYPTED, user.dest.addrstr)
         except KeyNotFound:
             # if key was not found, check config to see if will send anyway.
-            if self._config[ENCRYPTED_ONLY_KEY]:
+            if self._encrypted_only:
                 signal(proto.SMTP_RECIPIENT_REJECTED, user.dest.addrstr)
                 raise smtp.SMTPBadRcpt(user.dest.addrstr)
             log.msg("Warning: will send an unencrypted message (because "
@@ -297,17 +265,18 @@ class SMTPDelivery(object):
             signal(
                 proto.SMTP_RECIPIENT_ACCEPTED_UNENCRYPTED, user.dest.addrstr)
         return lambda: EncryptedMessage(
-            self._origin, user, self._km, self._config)
+            self._origin, user, self._km, self._host, self._port, self._cert,
+            self._key)
 
     def validateFrom(self, helo, origin):
         """
         Validate the address from which the message originates.
 
-        @param helo: The argument to the HELO command and the client's IP
+        :param helo: The argument to the HELO command and the client's IP
             address.
-        @type: (str, str)
-        @param origin: The address the message is from.
-        @type origin: twisted.mail.smtp.Address
+        :type: (str, str)
+        :param origin: The address the message is from.
+        :type origin: twisted.mail.smtp.Address
 
         @return: origin or a Deferred whose callback will be passed origin.
         @rtype: Deferred or Address
@@ -359,36 +328,36 @@ class EncryptedMessage(object):
     """
     implements(smtp.IMessage)
 
-    def __init__(self, fromAddress, user, keymanager, config):
+    def __init__(self, fromAddress, user, keymanager, host, port, cert, key):
         """
         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 config: A dictionary with smtp configuration. Should have
-            the following structure:
-                {
-                    HOST_KEY: '<str>',
-                    PORT_KEY: <int>,
-                    CERT_KEY: '<str>',
-                    KEY_KEY: '<str>',
-                    ENCRYPTED_ONLY_KEY: <bool>,
-                }
-        @type config: dict
+        :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
         """
         # assert params
         leap_assert_type(user, smtp.User)
         leap_assert_type(keymanager, KeyManager)
-        assert_config_structure(config)
         # and store them
         self._fromAddress = fromAddress
         self._user = user
         self._km = keymanager
-        self._config = config
+        self._host = host
+        self._port = port
+        self._cert = cert
+        self._key = key
         # initialize list for message's lines
         self.lines = []
 
@@ -400,8 +369,8 @@ class EncryptedMessage(object):
         """
         Handle another line.
 
-        @param line: The received line.
-        @type line: str
+        :param line: The received line.
+        :type line: str
         """
         self.lines.append(line)
 
@@ -440,8 +409,8 @@ class EncryptedMessage(object):
         """
         Callback for a successful send.
 
-        @param r: The result from the last previous callback in the chain.
-        @type r: anything
+        :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)
@@ -450,8 +419,8 @@ class EncryptedMessage(object):
         """
         Callback for an unsuccessfull send.
 
-        @param e: The result from the last errback.
-        @type e: anything
+        :param e: The result from the last errback.
+        :type e: anything
         """
         log.msg(e)
         log.err()
@@ -470,8 +439,7 @@ class EncryptedMessage(object):
         """
         msg = self._msg.as_string(False)
 
-        log.msg("Connecting to SMTP server %s:%s" % (self._config[HOST_KEY],
-                                                     self._config[PORT_KEY]))
+        log.msg("Connecting to SMTP server %s:%s" % (self._host, self._port))
 
         d = defer.Deferred()
         # we don't pass an ssl context factory to the ESMTPSenderFactory
@@ -487,11 +455,8 @@ class EncryptedMessage(object):
             requireTransportSecurity=True)
         signal(proto.SMTP_SEND_MESSAGE_START, self._user.dest.addrstr)
         reactor.connectSSL(
-            self._config[HOST_KEY],
-            self._config[PORT_KEY],
-            factory,
-            contextFactory=SSLContextFactory(self._config[CERT_KEY],
-                                             self._config[KEY_KEY]))
+            self._host, self._port, factory,
+            contextFactory=SSLContextFactory(self._cert, self._key))
         d.addCallback(self.sendSuccess)
         d.addErrback(self.sendError)
         return d
@@ -505,20 +470,18 @@ class EncryptedMessage(object):
         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: leap.common.keymanager.openpgp.OpenPGPKey
-        @param signkey: The private key used to sign the message.
-        @type signkey: leap.common.keymanager.openpgp.OpenPGPKey
+        :param pubkey: The public key used to encrypt the message.
+        :type pubkey: leap.common.keymanager.openpgp.OpenPGPKey
+        :param signkey: The private key used to sign the message.
+        :type signkey: leap.common.keymanager.openpgp.OpenPGPKey
         """
-        # parse original message from received lines
-        origmsg = self.parseMessage()
         # 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
-        move_headers(origmsg, newmsg)
+        move_headers(self._origmsg, newmsg)
         # create 'application/octet-stream' encrypted message
         encmsg = MIMEApplication(
-            self._km.encrypt(origmsg.as_string(unixfrom=False), pubkey,
+            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',
@@ -535,25 +498,23 @@ class EncryptedMessage(object):
         """
         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
+        :param signkey: The private key used to sign the message.
+        :type signkey: leap.common.keymanager.openpgp.OpenPGPKey
         """
-        # parse original message from received lines
-        origmsg = self.parseMessage()
         # create new multipart/signed message
         newmsg = MultipartSigned('application/pgp-signature', 'pgp-sha512')
         # move (almost) all headers from original message to the new message
-        move_headers(origmsg, newmsg)
+        move_headers(self._origmsg, newmsg)
         # apply base64 content-transfer-encoding
-        encode_base64_rec(origmsg)
+        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(origmsg)
+        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 origmsg.is_multipart():
+        if self._origmsg.is_multipart():
             if not msgtext.endswith("\r\n"):
                 msgtext += "\r\n"
         # calculate signature
@@ -561,23 +522,46 @@ class EncryptedMessage(object):
                                   clearsign=False, detach=True, binary=False)
         sigmsg = PGPSignature(signature)
         # attach original message and signature to new message
-        newmsg.attach(origmsg)
+        newmsg.attach(self._origmsg)
         newmsg.attach(sigmsg)
         self._msg = newmsg
 
     def _maybe_encrypt_and_sign(self):
         """
-        Encrypt the message body.
+        Attempt to encrypt and sign the outgoing message.
 
-        Fetch the recipient key and encrypt the content to the
-        recipient. If a key is not found, then the behaviour depends on the
-        configuration parameter ENCRYPTED_ONLY_KEY. If it is False, the message
-        is sent unencrypted and a warning is logged. If it is True, the
-        encryption fails with a KeyNotFound exception.
+        The behaviour of this method depends on:
 
-        @raise KeyNotFound: Raised when the recipient key was not found and
-            the ENCRYPTED_ONLY_KEY configuration parameter is set to True.
+            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)
         signkey = self._km.get_key(from_address, OpenPGPKey, private=True)
         log.msg("Will sign the message with %s." % signkey.fingerprint)
diff --git a/src/leap/mail/smtp/tests/__init__.py b/src/leap/mail/smtp/tests/__init__.py
index 9b54de3..62b015f 100644
--- a/src/leap/mail/smtp/tests/__init__.py
+++ b/src/leap/mail/smtp/tests/__init__.py
@@ -17,7 +17,7 @@
 
 
 """
-Base classes and keys for SMTP relay tests.
+Base classes and keys for SMTP gateway tests.
 """
 
 import os
@@ -59,7 +59,7 @@ class TestCaseWithKeyManager(BaseLeapTest):
         # setup our own stuff
         address = 'leap@leap.se'  # user's address in the form user@provider
         uuid = 'leap@leap.se'
-        passphrase = '123'
+        passphrase = u'123'
         secrets_path = os.path.join(self.tempdir, 'secret.gpg')
         local_db_path = os.path.join(self.tempdir, 'soledad.u1db')
         server_url = 'http://provider/'
@@ -88,6 +88,8 @@ class TestCaseWithKeyManager(BaseLeapTest):
 
             get_doc = Mock(return_value=None)
             put_doc = Mock(side_effect=_put_doc_side_effect)
+            lock = Mock(return_value=('atoken', 300))
+            unlock = Mock(return_value=True)
 
             def __call__(self):
                 return self
diff --git a/src/leap/mail/smtp/tests/test_smtprelay.py b/src/leap/mail/smtp/tests/test_gateway.py
index 7fefe77..f9ea027 100644
--- a/src/leap/mail/smtp/tests/test_smtprelay.py
+++ b/src/leap/mail/smtp/tests/test_gateway.py
@@ -1,5 +1,5 @@
 # -*- coding: utf-8 -*-
-# test_smtprelay.py
+# test_gateway.py
 # Copyright (C) 2013 LEAP
 #
 # This program is free software: you can redistribute it and/or modify
@@ -17,7 +17,7 @@
 
 
 """
-SMTP relay tests.
+SMTP gateway tests.
 """
 
 
@@ -33,7 +33,7 @@ from twisted.mail.smtp import (
 )
 from mock import Mock
 
-from leap.mail.smtp.smtprelay import (
+from leap.mail.smtp.gateway import (
     SMTPFactory,
     EncryptedMessage,
 )
@@ -52,9 +52,9 @@ HOSTNAME_REGEX = "(([a-zA-Z0-9]|[a-zA-Z0-9][a-zA-Z0-9\-]*[a-zA-Z0-9])\.)*" + \
 IP_OR_HOST_REGEX = '(' + IP_REGEX + '|' + HOSTNAME_REGEX + ')'
 
 
-class TestSmtpRelay(TestCaseWithKeyManager):
+class TestSmtpGateway(TestCaseWithKeyManager):
 
-    EMAIL_DATA = ['HELO relay.leap.se',
+    EMAIL_DATA = ['HELO gateway.leap.se',
                   'MAIL FROM: <%s>' % ADDRESS_2,
                   'RCPT TO: <%s>' % ADDRESS,
                   'DATA',
@@ -90,7 +90,7 @@ class TestSmtpRelay(TestCaseWithKeyManager):
         self.assertEqual(text, decrypted,
                          "Decrypted text differs from plaintext.")
 
-    def test_relay_accepts_valid_email(self):
+    def test_gateway_accepts_valid_email(self):
         """
         Test if SMTP server responds correctly for valid interaction.
         """
@@ -102,26 +102,32 @@ class TestSmtpRelay(TestCaseWithKeyManager):
                         '250 Sender address accepted',
                         '250 Recipient address accepted',
                         '354 Continue']
-        proto = SMTPFactory(
-            self._km, self._config).buildProtocol(('127.0.0.1', 0))
+        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))
         transport = proto_helpers.StringTransport()
         proto.makeConnection(transport)
         for i, line in enumerate(self.EMAIL_DATA):
             proto.lineReceived(line + '\r\n')
             self.assertMatch(transport.value(),
                              '\r\n'.join(SMTP_ANSWERS[0:i + 1]),
-                             'Did not get expected answer from relay.')
+                             '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(
-            self._km, self._config).buildProtocol(('127.0.0.1', 0))
+        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, 'relay.leap.se', proto, ADDRESS)
-        m = EncryptedMessage(fromAddr, dest, self._km, self._config)
+        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()
@@ -149,11 +155,15 @@ class TestSmtpRelay(TestCaseWithKeyManager):
         Test if message gets encrypted to destination email and signed with
         sender key.
         """
-        proto = SMTPFactory(
-            self._km, self._config).buildProtocol(('127.0.0.1', 0))
-        user = User(ADDRESS, 'relay.leap.se', proto, ADDRESS)
+        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)
+        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
@@ -185,11 +195,15 @@ class TestSmtpRelay(TestCaseWithKeyManager):
         """
         # mock the key fetching
         self._km.fetch_keys_from_server = Mock(return_value=[])
-        proto = SMTPFactory(
-            self._km, self._config).buildProtocol(('127.0.0.1', 0))
-        user = User('ihavenopubkey@nonleap.se', 'relay.leap.se', proto, ADDRESS)
+        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)
+        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
@@ -237,8 +251,10 @@ class TestSmtpRelay(TestCaseWithKeyManager):
         # mock the key fetching
         self._km.fetch_keys_from_server = Mock(return_value=[])
         # prepare the SMTP factory
-        proto = SMTPFactory(
-            self._km, self._config).buildProtocol(('127.0.0.1', 0))
+        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))
         transport = proto_helpers.StringTransport()
         proto.makeConnection(transport)
         proto.lineReceived(self.EMAIL_DATA[0] + '\r\n')
@@ -263,11 +279,11 @@ class TestSmtpRelay(TestCaseWithKeyManager):
         pgp.delete_key(pubkey)
         # mock the key fetching
         self._km.fetch_keys_from_server = Mock(return_value=[])
-        # change the configuration
-        self._config['encrypted_only'] = False
-        # prepare the SMTP factory
-        proto = SMTPFactory(
-            self._km, self._config).buildProtocol(('127.0.0.1', 0))
+        # 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))
         transport = proto_helpers.StringTransport()
         proto.makeConnection(transport)
         proto.lineReceived(self.EMAIL_DATA[0] + '\r\n')