[pkg] move mail source to leap.bitmask.mail

10 files changed, 1022 insertions, 0 deletions

diff --git a/src/leap/bitmask/mail/smtp/README.rst b/src/leap/bitmask/mail/smtp/README.rst
new file mode 100644
index 00000000..1d3a9038
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/README.rst
@@ -0,0 +1,44 @@
+Leap SMTP Gateway
+=================
+
+The Bitmask Client runs a thin SMTP gateway on the user's device, which
+intends to encrypt and sign outgoing messages to achieve point to point
+encryption.
+
+The gateway is bound to localhost and the user's MUA should be configured to
+send messages to it. After doing its thing, the gateway will relay the
+messages to the remote SMTP server.
+
+Outgoing mail workflow:
+
+  * SMTP gateway receives a message from the MUA.
+
+  * SMTP gateway queries Key Manager for the user's private key.
+
+  * For each recipient (including addresses in "To", "Cc" anc "Bcc" fields),
+    the following happens:
+
+    - The recipient's address is validated against RFC2822.
+
+    - An attempt is made to fetch the recipient's public PGP key.
+
+    - If key is not found:
+
+      - If the gateway is configured to only send encrypted messages the
+        recipient is rejected.
+
+      - Otherwise, the message is signed and sent as plain text.
+
+    - If the key is found, the message is encrypted to the recipient and
+      signed with the sender's private PGP key.
+
+  * Finally, one message for each recipient is gatewayed to provider's SMTP
+    server.
+
+
+Running tests
+-------------
+
+Tests are run using Twisted's Trial API, like this::
+
+    python setup.py test -s leap.mail.gateway.tests
diff --git a/src/leap/bitmask/mail/smtp/__init__.py b/src/leap/bitmask/mail/smtp/__init__.py
new file mode 100644
index 00000000..9fab70a7
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/__init__.py
@@ -0,0 +1,73 @@
+# -*- coding: utf-8 -*-
+# __init__.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 helper function.
+"""
+import logging
+import os
+
+from twisted.internet import reactor
+from twisted.internet.error import CannotListenError
+
+from leap.common.events import emit_async, catalog
+
+from leap.mail.smtp.gateway import SMTPFactory
+
+logger = logging.getLogger(__name__)
+
+
+SMTP_PORT = 2013
+
+
+def run_service(soledad_sessions, keymanager_sessions, sendmail_opts,
+                port=SMTP_PORT):
+    """
+    Main entry point to run the service from the client.
+
+    :param soledad_sessions: a dict-like object, containing instances
+                             of a Store (soledad instances), indexed by userid.
+    :param keymanager_sessions: a dict-like object, containing instances
+                                of Keymanager, indexed by userid.
+    :param sendmail_opts: a dict-like object of sendmailOptions.
+
+    :returns: the port as returned by the reactor when starts listening, and
+              the factory for the protocol.
+    :rtype: tuple
+    """
+    factory = SMTPFactory(soledad_sessions, keymanager_sessions,
+                          sendmail_opts)
+
+    try:
+        interface = "localhost"
+        # don't bind just to localhost if we are running on docker since we
+        # won't be able to access smtp from the host
+        if os.environ.get("LEAP_DOCKERIZED"):
+            interface = ''
+
+        # TODO Use Endpoints instead --------------------------------
+        tport = reactor.listenTCP(port, factory, interface=interface)
+        emit_async(catalog.SMTP_SERVICE_STARTED, str(port))
+
+        return factory, tport
+    except CannotListenError:
+        logger.error("STMP Service failed to start: "
+                     "cannot listen in port %s" % port)
+        emit_async(catalog.SMTP_SERVICE_FAILED_TO_START, str(port))
+    except Exception as exc:
+        logger.error("Unhandled error while launching smtp gateway service")
+        logger.exception(exc)
diff --git a/src/leap/bitmask/mail/smtp/bounces.py b/src/leap/bitmask/mail/smtp/bounces.py
new file mode 100644
index 00000000..7a4674b9
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/bounces.py
@@ -0,0 +1,90 @@
+# -*- coding: utf-8 -*-
+# bounces.py
+# Copyright (C) 2016 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/>.
+"""
+Deliver bounces to the user Inbox.
+"""
+import time
+from email.message import Message
+from email.utils import formatdate
+
+from leap.mail.constants import INBOX_NAME
+from leap.mail.mail import Account
+
+
+# TODO implement localization for this template.
+
+BOUNCE_TEMPLATE = """This is your local Bitmask Mail Agent running at localhost.
+
+I'm sorry to have to inform you that your message could not be delivered to one
+or more recipients.
+
+The reasons I got for the error are:
+
+{raw_error}
+
+If the problem persists and it's not a network connectivity issue, you might
+want to contact your provider ({provider}) with this information (remove any
+sensitive data before).
+
+--- Original message (*before* it was encrypted by bitmask) below ----:
+
+{orig}"""
+
+
+class Bouncer(object):
+    """
+    Implements a mechanism to deliver bounces to user inbox.
+    """
+    # TODO this should follow RFC 6522, and compose a correct multipart
+    # attaching the report and the original message. Leaving this for a future
+    # iteration.
+
+    def __init__(self, inbox_collection):
+        self._inbox_collection = inbox_collection
+
+    def bounce_message(self, error_data, to, date=None, orig=''):
+        if not date:
+            date = formatdate(time.time())
+
+        raw_data = self._format_msg(error_data, to, date, orig)
+        d = self._inbox_collection.add_msg(
+            raw_data, ('\\Recent',), date=date)
+        return d
+
+    def _format_msg(self, error_data, to, date, orig):
+        provider = to.split('@')[1]
+
+        msg = Message()
+        msg.add_header(
+            'From', 'bitmask-bouncer@localhost (Bitmask Local Agent)')
+        msg.add_header('To', to)
+        msg.add_header('Subject', 'Undelivered Message')
+        msg.add_header('Date', date)
+        msg.set_payload(BOUNCE_TEMPLATE.format(
+            raw_error=error_data,
+            provider=provider,
+            orig=orig))
+
+        return msg.as_string()
+
+
+def bouncerFactory(soledad):
+    user_id = soledad.uuid
+    acc = Account(soledad, user_id)
+    d = acc.callWhenReady(lambda _: acc.get_collection_by_mailbox(INBOX_NAME))
+    d.addCallback(lambda inbox: Bouncer(inbox))
+    return d
diff --git a/src/leap/bitmask/mail/smtp/gateway.py b/src/leap/bitmask/mail/smtp/gateway.py
new file mode 100644
index 00000000..e49bbe82
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/gateway.py
@@ -0,0 +1,413 @@
+# -*- coding: utf-8 -*-
+# 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/>.
+"""
+LEAP SMTP encrypted gateway.
+
+The following classes comprise the SMTP gateway service:
+
+    * SMTPFactory - A twisted.internet.protocol.ServerFactory that provides
+      the SMTPDelivery protocol.
+
+    * SMTPDelivery - A twisted.mail.smtp.IMessageDelivery implementation. It
+      knows how to validate sender and receiver of messages and it generates
+      an EncryptedMessage for each recipient.
+
+    * EncryptedMessage - An implementation of twisted.mail.smtp.IMessage that
+      knows how to encrypt/sign itself before sending.
+"""
+from email.Header import Header
+
+from zope.interface import implements
+from zope.interface import implementer
+
+from twisted.cred.portal import Portal, IRealm
+from twisted.mail import smtp
+from twisted.mail.imap4 import LOGINCredentials, PLAINCredentials
+from twisted.internet import defer, protocol
+from twisted.python import log
+
+from leap.common.check import leap_assert_type
+from leap.common.events import emit_async, catalog
+from leap.mail import errors
+from leap.mail.cred import LocalSoledadTokenChecker
+from leap.mail.utils import validate_address
+from leap.mail.rfc3156 import RFC3156CompliantGenerator
+from leap.mail.outgoing.service import outgoingFactory
+from leap.mail.smtp.bounces import bouncerFactory
+from leap.keymanager.errors import KeyNotFound
+
+# replace email generator with a RFC 3156 compliant one.
+from email import generator
+
+generator.Generator = RFC3156CompliantGenerator
+
+
+LOCAL_FQDN = "bitmask.local"
+
+
+@implementer(IRealm)
+class LocalSMTPRealm(object):
+
+    _encoding = 'utf-8'
+
+    def __init__(self, keymanager_sessions, soledad_sessions, sendmail_opts,
+                 encrypted_only=False):
+        """
+        :param keymanager_sessions: a dict-like object, containing instances
+                                 of a Keymanager objects, indexed by
+                                 userid.
+        """
+        self._keymanager_sessions = keymanager_sessions
+        self._soledad_sessions = soledad_sessions
+        self._sendmail_opts = sendmail_opts
+        self.encrypted_only = encrypted_only
+
+    def requestAvatar(self, avatarId, mind, *interfaces):
+
+        if isinstance(avatarId, str):
+            avatarId = avatarId.decode(self._encoding)
+
+        def gotKeymanagerAndSoledad(result):
+            keymanager, soledad = result
+            d = bouncerFactory(soledad)
+            d.addCallback(lambda bouncer: (keymanager, soledad, bouncer))
+            return d
+
+        def getMessageDelivery(result):
+            keymanager, soledad, bouncer = result
+            # TODO use IMessageDeliveryFactory instead ?
+            # it could reuse the connections.
+            if smtp.IMessageDelivery in interfaces:
+                userid = avatarId
+                opts = self.getSendingOpts(userid)
+
+                outgoing = outgoingFactory(
+                    userid, keymanager, opts, bouncer=bouncer)
+                avatar = SMTPDelivery(userid, keymanager, self.encrypted_only,
+                                      outgoing)
+
+                return (smtp.IMessageDelivery, avatar,
+                        getattr(avatar, 'logout', lambda: None))
+
+            raise NotImplementedError(self, interfaces)
+
+        d1 = self.lookupKeymanagerInstance(avatarId)
+        d2 = self.lookupSoledadInstance(avatarId)
+        d = defer.gatherResults([d1, d2])
+        d.addCallback(gotKeymanagerAndSoledad)
+        d.addCallback(getMessageDelivery)
+        return d
+
+    def lookupKeymanagerInstance(self, userid):
+        try:
+            keymanager = self._keymanager_sessions[userid]
+        except:
+            raise errors.AuthenticationError(
+                'No keymanager session found for user %s. Is it authenticated?'
+                % userid)
+        # XXX this should return the instance after whenReady callback
+        return defer.succeed(keymanager)
+
+    def lookupSoledadInstance(self, userid):
+        try:
+            soledad = self._soledad_sessions[userid]
+        except:
+            raise errors.AuthenticationError(
+                'No soledad session found for user %s. Is it authenticated?'
+                % userid)
+        # XXX this should return the instance after whenReady callback
+        return defer.succeed(soledad)
+
+    def getSendingOpts(self, userid):
+        try:
+            opts = self._sendmail_opts[userid]
+        except KeyError:
+            raise errors.ConfigurationError(
+                'No sendingMail options found for user %s' % userid)
+        return opts
+
+
+class SMTPTokenChecker(LocalSoledadTokenChecker):
+    """A credentials checker that will lookup a token for the SMTP service.
+    For now it will be using the same identifier than IMAPTokenChecker"""
+
+    service = 'mail_auth'
+
+    # TODO besides checking for token credential,
+    # we could also verify the certificate here.
+
+
+class LEAPInitMixin(object):
+
+    """
+    A Mixin that takes care of initialization of all the data needed to access
+    LEAP sessions.
+    """
+    def __init__(self, soledad_sessions, keymanager_sessions, sendmail_opts,
+                 encrypted_only=False):
+        realm = LocalSMTPRealm(
+            keymanager_sessions, soledad_sessions, sendmail_opts,
+            encrypted_only)
+        portal = Portal(realm)
+
+        checker = SMTPTokenChecker(soledad_sessions)
+        self.checker = checker
+        self.portal = portal
+        portal.registerChecker(checker)
+
+
+class LocalSMTPServer(smtp.ESMTP, LEAPInitMixin):
+    """
+    The Production ESMTP Server: Authentication Needed.
+    Authenticates against SMTP Token stored in Local Soledad instance.
+    The Realm will produce a Delivery Object that handles encryption/signing.
+    """
+
+    # TODO: implement Queue using twisted.mail.mail.MailService
+
+    def __init__(self, soledads, keyms, sendmailopts, *args, **kw):
+        encrypted_only = kw.pop('encrypted_only', False)
+
+        LEAPInitMixin.__init__(self, soledads, keyms, sendmailopts,
+                               encrypted_only)
+        smtp.ESMTP.__init__(self, *args, **kw)
+
+
+# TODO implement retries -- see smtp.SenderMixin
+class SMTPFactory(protocol.ServerFactory):
+    """
+    Factory for an SMTP server with encrypted gatewaying capabilities.
+    """
+
+    protocol = LocalSMTPServer
+    domain = LOCAL_FQDN
+    timeout = 600
+    encrypted_only = False
+
+    def __init__(self, soledad_sessions, keymanager_sessions, sendmail_opts,
+                 deferred=None, retries=3):
+
+        self._soledad_sessions = soledad_sessions
+        self._keymanager_sessions = keymanager_sessions
+        self._sendmail_opts = sendmail_opts
+
+    def buildProtocol(self, addr):
+        p = self.protocol(
+            self._soledad_sessions, self._keymanager_sessions,
+            self._sendmail_opts, encrypted_only=self.encrypted_only)
+        p.factory = self
+        p.host = LOCAL_FQDN
+        p.challengers = {"LOGIN": LOGINCredentials, "PLAIN": PLAINCredentials}
+        return p
+
+
+#
+# SMTPDelivery
+#
+
+@implementer(smtp.IMessageDelivery)
+class SMTPDelivery(object):
+    """
+    Validate email addresses and handle message delivery.
+    """
+
+    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 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.outgoing.service.OutgoingMail
+        """
+        self._userid = userid
+        self._outgoing_mail = outgoing_mail
+        self._km = keymanager
+        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
+            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
+            bound.
+        :type: list of twisted.mail.smtp.User
+
+        @return: The full "Received" header string.
+        :type: str
+        """
+        myHostname, clientIP = helo
+        headerValue = "by bitmask.local from %s with ESMTP ; %s" % (
+            clientIP, smtp.rfc822date())
+        # email.Header.Header used for automatic wrapping of long lines
+        return "Received: %s" % Header(s=headerValue, header_name='Received')
+
+    def validateTo(self, user):
+        """
+        Validate the address of a recipient of the message, possibly
+        rejecting it if the recipient key is not available.
+
+        This method is called once for each recipient, i.e. for each SMTP
+        protocol line beginning with "RCPT TO:", which includes all addresses
+        in "To", "Cc" and "Bcc" MUA fields.
+
+        The recipient's address is validated against the RFC 2822 definition.
+        If self._encrypted_only is True and no key is found for a recipient,
+        then that recipient is rejected.
+
+        The method returns an encrypted message object that is able to send
+        itself to the user's address.
+
+        :param user: The user whose address we wish to validate.
+        :type: twisted.mail.smtp.User
+
+        @return: A callable which takes no arguments and returns an
+                 encryptedMessage.
+        @rtype: no-argument callable
+
+        @raise SMTPBadRcpt: Raised if messages to the address are not to be
+                            accepted.
+        """
+        # try to find recipient's public key
+        address = validate_address(user.dest.addrstr)
+
+        # verify if recipient key is available in keyring
+        def found(_):
+            log.msg("Accepting mail for %s..." % user.dest.addrstr)
+            emit_async(catalog.SMTP_RECIPIENT_ACCEPTED_ENCRYPTED,
+                       self._userid, user.dest.addrstr)
+
+        def not_found(failure):
+            failure.trap(KeyNotFound)
+
+            # if key was not found, check config to see if will send anyway
+            if self._encrypted_only:
+                emit_async(catalog.SMTP_RECIPIENT_REJECTED, self._userid,
+                           user.dest.addrstr)
+                raise smtp.SMTPBadRcpt(user.dest.addrstr)
+            log.msg("Warning: will send an unencrypted message (because "
+                    "encrypted_only' is set to False).")
+            emit_async(
+                catalog.SMTP_RECIPIENT_ACCEPTED_UNENCRYPTED,
+                self._userid, user.dest.addrstr)
+
+        def encrypt_func(_):
+            return lambda: EncryptedMessage(user, self._outgoing_mail)
+
+        d = self._km.get_key(address)
+        d.addCallbacks(found, not_found)
+        d.addCallback(encrypt_func)
+        return d
+
+    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
+            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
+
+        @raise twisted.mail.smtp.SMTPBadSender: Raised if messages from this
+            address are not to be accepted.
+        """
+        # accept mail from anywhere. To reject an address, raise
+        # smtp.SMTPBadSender here.
+        if str(origin) != str(self._userid):
+            log.msg("Rejecting sender {0}, expected {1}".format(origin,
+                                                                self._userid))
+            raise smtp.SMTPBadSender(origin)
+        self._origin = origin
+        return origin
+
+
+#
+# EncryptedMessage
+#
+
+class EncryptedMessage(object):
+    """
+    Receive plaintext from client, encrypt it and send message to a
+    recipient.
+    """
+    implements(smtp.IMessage)
+
+    def __init__(self, user, outgoing_mail):
+        """
+        Initialize the encrypted message.
+
+        :param user: The recipient of this message.
+        :type user: twisted.mail.smtp.User
+        :param outgoing_mail: The outgoing mail to send the message
+        :type outgoing_mail: leap.mail.outgoing.service.OutgoingMail
+        """
+        # assert params
+        leap_assert_type(user, smtp.User)
+
+        self._user = user
+        self._lines = []
+        self._outgoing_mail = outgoing_mail
+
+    def lineReceived(self, line):
+        """
+        Handle another line.
+
+        :param line: The received line.
+        :type line: str
+        """
+        self._lines.append(line)
+
+    def eomReceived(self):
+        """
+        Handle end of message.
+
+        This method will encrypt and send the message.
+
+        :returns: a deferred
+        """
+        log.msg("Message data complete.")
+        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):
+        """
+        Log an error when the connection is lost.
+        """
+        log.msg("Connection lost unexpectedly!")
+        log.err()
+        emit_async(catalog.SMTP_CONNECTION_LOST, self._userid,
+                   self._user.dest.addrstr)
+        # unexpected loss of connection; don't save
+
+        self._lines = []
diff --git a/src/leap/bitmask/mail/smtp/tests/185CA770.key b/src/leap/bitmask/mail/smtp/tests/185CA770.key
new file mode 100644
index 00000000..587b4164
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/tests/185CA770.key
@@ -0,0 +1,79 @@
+-----BEGIN PGP PRIVATE KEY BLOCK-----
+Version: GnuPG v1.4.10 (GNU/Linux)
+
+lQIVBFCJNL4BEADFsI1TCD4yq7ZqL7VhdVviTuX6JUps8/mVEhRVOZhojLcTYaqQ
+gs6T6WabRxcK7ymOnf4K8NhYdz6HFoJN46BT87etokx7J/Sl2OhpiqBQEY+jW8Rp
++3MSGrGmvFw0s1lGrz/cXzM7UNgWSTOnYZ5nJS1veMhy0jseZOUK7ekp2oEDjGZh
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+W1lE0V7pwnN2NTOYfBMi+WloCs/bp4iZSr4QP1duZ3IqKraeBDCk7MoFo4A9Wk07
+kvqPwF9IBgatu62WVEZIzwyViN+asFUGfgp+8D7gtnlWAw0V6y/lSTzyl+dnLP98
+Hfr2eLBylFs+Kl3Pivpg2uHw09LLCrjeLEN3dj9SfBbA9jDIo9Zhs1voiIK/7Shx
+E0BRJaBgG3C4QaytYEu7RFFOKuvBai9w2Y5OfsKFo8rA7v4dxFFDvzKGujCtNnwf
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diff --git a/src/leap/bitmask/mail/smtp/tests/185CA770.pub b/src/leap/bitmask/mail/smtp/tests/185CA770.pub
new file mode 100644
index 00000000..38af19f8
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/tests/185CA770.pub
@@ -0,0 +1,52 @@
+-----BEGIN PGP PUBLIC KEY BLOCK-----
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diff --git a/src/leap/bitmask/mail/smtp/tests/cert/server.crt b/src/leap/bitmask/mail/smtp/tests/cert/server.crt
new file mode 100644
index 00000000..a27391c2
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/tests/cert/server.crt
@@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE-----
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diff --git a/src/leap/bitmask/mail/smtp/tests/cert/server.key b/src/leap/bitmask/mail/smtp/tests/cert/server.key
new file mode 100644
index 00000000..197a4496
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/tests/cert/server.key
@@ -0,0 +1,51 @@
+-----BEGIN RSA PRIVATE KEY-----
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+s+AgrZ4qYmskrFaD0PHakWsQNHGC8yOh80lgE3Gl4nxSGAvkcR7dkSmsIQFL
+-----END RSA PRIVATE KEY-----
diff --git a/src/leap/bitmask/mail/smtp/tests/mail.txt b/src/leap/bitmask/mail/smtp/tests/mail.txt
new file mode 100644
index 00000000..95420470
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/tests/mail.txt
@@ -0,0 +1,10 @@
+HELO drebs@riseup.net
+MAIL FROM: drebs@riseup.net
+RCPT TO: drebs@riseup.net
+RCPT TO: drebs@leap.se
+DATA
+Subject: leap test
+
+Hello world!
+.
+QUIT
diff --git a/src/leap/bitmask/mail/smtp/tests/test_gateway.py b/src/leap/bitmask/mail/smtp/tests/test_gateway.py
new file mode 100644
index 00000000..9d88afb8
--- /dev/null
+++ b/src/leap/bitmask/mail/smtp/tests/test_gateway.py
@@ -0,0 +1,181 @@
+# -*- 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
+import tempfile
+from datetime import datetime
+
+from twisted.internet import reactor
+from twisted.internet.defer import inlineCallbacks, fail, succeed, Deferred
+from twisted.test import proto_helpers
+
+from mock import Mock
+
+from leap.keymanager import openpgp, errors
+from leap.mail.testing import KeyManagerWithSoledadTestCase
+from leap.mail.testing import ADDRESS, ADDRESS_2
+from leap.mail.testing.smtp import getSMTPFactory, TEST_USER
+
+
+# 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])"
+HOSTNAME_REGEX = "(([a-zA-Z0-9]|[a-zA-Z0-9][a-zA-Z0-9\-]*[a-zA-Z0-9])\.)*" + \
+    "([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 TestSmtpGateway(KeyManagerWithSoledadTestCase):
+
+    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):
+        # pytest handles correctly the setupEnv for the class,
+        # but trial ignores it.
+        if not getattr(self, 'tempdir', None):
+            self.tempdir = tempfile.mkdtemp()
+        return KeyManagerWithSoledadTestCase.setUp(self)
+
+    def tearDown(self):
+        return KeyManagerWithSoledadTestCase.tearDown(self)
+
+    def assertMatch(self, string, pattern, msg=None):
+        if not re.match(pattern, string):
+            msg = self._formatMessage(msg, '"%s" does not match pattern "%s".'
+                                           % (string, pattern))
+            raise self.failureException(msg)
+
+    @inlineCallbacks
+    def test_gateway_accepts_valid_email(self):
+        """
+        Test if SMTP server responds correctly for valid interaction.
+        """
+
+        SMTP_ANSWERS = ['220 ' + IP_OR_HOST_REGEX +
+                        ' NO UCE NO UBE NO RELAY PROBES',
+                        '250 ' + IP_OR_HOST_REGEX + ' Hello ' +
+                        IP_OR_HOST_REGEX + ', nice to meet you',
+                        '250 Sender address accepted',
+                        '250 Recipient address accepted',
+                        '354 Continue']
+
+        user = TEST_USER
+        proto = getSMTPFactory({user: None}, {user: self.km}, {user: None})
+        transport = proto_helpers.StringTransport()
+        proto.makeConnection(transport)
+        reply = ""
+        for i, line in enumerate(self.EMAIL_DATA):
+            reply += yield self.getReply(line + '\r\n', proto, transport)
+        self.assertMatch(reply, '\r\n'.join(SMTP_ANSWERS),
+                         'Did not get expected answer from gateway.')
+        proto.setTimeout(None)
+
+    @inlineCallbacks
+    def test_missing_key_rejects_address(self):
+        """
+        Test if server rejects to send unencrypted when 'encrypted_only' is
+        True.
+        """
+        # remove key from key manager
+        pubkey = yield self.km.get_key(ADDRESS)
+        pgp = openpgp.OpenPGPScheme(
+            self._soledad, gpgbinary=self.gpg_binary_path)
+        yield pgp.delete_key(pubkey)
+        # mock the key fetching
+        self.km._fetch_keys_from_server = Mock(
+            return_value=fail(errors.KeyNotFound()))
+        user = TEST_USER
+        proto = getSMTPFactory(
+            {user: None}, {user: self.km}, {user: None},
+            encrypted_only=True)
+        transport = proto_helpers.StringTransport()
+        proto.makeConnection(transport)
+        yield self.getReply(self.EMAIL_DATA[0] + '\r\n', proto, transport)
+        yield self.getReply(self.EMAIL_DATA[1] + '\r\n', proto, transport)
+        reply = yield self.getReply(self.EMAIL_DATA[2] + '\r\n',
+                                    proto, transport)
+        # ensure the address was rejected
+        self.assertEqual(
+            '550 Cannot receive for specified address\r\n',
+            reply,
+            'Address should have been rejected with appropriate message.')
+        proto.setTimeout(None)
+
+    @inlineCallbacks
+    def test_missing_key_accepts_address(self):
+        """
+        Test if server accepts to send unencrypted when 'encrypted_only' is
+        False.
+        """
+        # remove key from key manager
+        pubkey = yield self.km.get_key(ADDRESS)
+        pgp = openpgp.OpenPGPScheme(
+            self._soledad, gpgbinary=self.gpg_binary_path)
+        yield pgp.delete_key(pubkey)
+        # mock the key fetching
+        self.km._fetch_keys_from_server = Mock(
+            return_value=fail(errors.KeyNotFound()))
+        user = TEST_USER
+        proto = getSMTPFactory({user: None}, {user: self.km}, {user: None})
+        transport = proto_helpers.StringTransport()
+        proto.makeConnection(transport)
+        yield self.getReply(self.EMAIL_DATA[0] + '\r\n', proto, transport)
+        yield self.getReply(self.EMAIL_DATA[1] + '\r\n', proto, transport)
+        reply = yield self.getReply(self.EMAIL_DATA[2] + '\r\n',
+                                    proto, transport)
+        # ensure the address was accepted
+        self.assertEqual(
+            '250 Recipient address accepted\r\n',
+            reply,
+            'Address should have been accepted with appropriate message.')
+        proto.setTimeout(None)
+
+    def getReply(self, line, proto, transport):
+        proto.lineReceived(line)
+
+        if line[:4] not in ['HELO', 'MAIL', 'RCPT', 'DATA']:
+            return succeed("")
+
+        def check_transport(_):
+            reply = transport.value()
+            if reply:
+                transport.clear()
+                return succeed(reply)
+
+            d = Deferred()
+            d.addCallback(check_transport)
+            reactor.callLater(0, lambda: d.callback(None))
+            return d
+
+        return check_transport(None)