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

3 files changed, 781 insertions, 0 deletions

diff --git a/src/leap/bitmask/mail/outgoing/__init__.py b/src/leap/bitmask/mail/outgoing/__init__.py
new file mode 100644
index 00000000..e69de29b
--- /dev/null
+++ b/src/leap/bitmask/mail/outgoing/__init__.py
diff --git a/src/leap/bitmask/mail/outgoing/service.py b/src/leap/bitmask/mail/outgoing/service.py
new file mode 100644
index 00000000..8b02f2e4
--- /dev/null
+++ b/src/leap/bitmask/mail/outgoing/service.py
@@ -0,0 +1,518 @@
+# -*- coding: utf-8 -*-
+# outgoing/service.py
+# Copyright (C) 2013-2015 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/>.
+
+"""
+OutgoingMail module.
+
+The OutgoingMail class allows to send mail, and encrypts/signs it if needed.
+"""
+
+import os.path
+import re
+from StringIO import StringIO
+from copy import deepcopy
+from email.parser import Parser
+from email.mime.application import MIMEApplication
+from email.mime.multipart import MIMEMultipart
+from email.mime.text import MIMEText
+
+from OpenSSL import SSL
+
+from twisted.mail import smtp
+from twisted.internet import reactor
+from twisted.internet import defer
+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 emit_async, catalog
+from leap.keymanager.errors import KeyNotFound, KeyAddressMismatch
+from leap.mail import __version__
+from leap.mail import errors
+from leap.mail.utils import validate_address
+from leap.mail.rfc3156 import MultipartEncrypted
+from leap.mail.rfc3156 import MultipartSigned
+from leap.mail.rfc3156 import encode_base64_rec
+from leap.mail.rfc3156 import RFC3156CompliantGenerator
+from leap.mail.rfc3156 import PGPSignature
+from leap.mail.rfc3156 import PGPEncrypted
+
+# TODO
+# [ ] rename this module to something else, service should be the implementor
+#     of IService
+
+
+class SSLContextFactory(ssl.ClientContextFactory):
+    def __init__(self, cert, key):
+        self.cert = cert
+        self.key = key
+
+    def getContext(self):
+        # FIXME -- we should use sslv23 to allow for tlsv1.2
+        # and, if possible, explicitely disable sslv3 clientside.
+        # Servers should avoid sslv3
+        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
+
+
+def outgoingFactory(userid, keymanager, opts, check_cert=True, bouncer=None):
+
+    cert = unicode(opts.cert)
+    key = unicode(opts.key)
+    hostname = str(opts.hostname)
+    port = opts.port
+
+    if check_cert:
+        if not os.path.isfile(cert):
+            raise errors.ConfigurationError(
+                'No valid SMTP certificate could be found for %s!' % userid)
+
+    return OutgoingMail(
+        str(userid), keymanager, cert, key, hostname, port,
+        bouncer)
+
+
+class OutgoingMail(object):
+    """
+    Sends Outgoing Mail, encrypting and signing if needed.
+    """
+
+    def __init__(self, from_address, keymanager, cert, key, host, port,
+                 bouncer=None):
+        """
+        Initialize the outgoing 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
+        """
+
+        # assert params
+        leap_assert_type(from_address, str)
+        leap_assert('@' in from_address)
+
+        # XXX it can be a zope.proxy too
+        # 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
+        self._bouncer = bouncer
+
+    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 = self._maybe_encrypt_and_sign(raw, recipient)
+        d.addCallback(self._route_msg, raw)
+        d.addErrback(self.sendError, raw)
+        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]
+        fromaddr = self._from_address
+        log.msg('Message sent from %s to %s' % (fromaddr, dest_addrstr))
+        emit_async(catalog.SMTP_SEND_MESSAGE_SUCCESS,
+                   fromaddr, dest_addrstr)
+
+    def sendError(self, failure, origmsg):
+        """
+        Callback for an unsuccessfull send.
+
+        :param failure: The result from the last errback.
+        :type failure: anything
+        :param origmsg: the original, unencrypted, raw message, to be passed to
+                        the bouncer.
+        :type origmsg: str
+        """
+        # XXX: need to get the address from the original message to send signal
+        # emit_async(catalog.SMTP_SEND_MESSAGE_ERROR, self._from_address,
+        #   self._user.dest.addrstr)
+
+        # TODO when we implement outgoing queues/long-term-retries, we could
+        # examine the error *here* and delay the notification if it's just a
+        # temporal error. We might want to notify the permanent errors
+        # differently.
+
+        err = failure.value
+        log.err(err)
+
+        if self._bouncer:
+            self._bouncer.bounce_message(
+                err.message, to=self._from_address,
+                orig=origmsg)
+        else:
+            raise err
+
+    def _route_msg(self, encrypt_and_sign_result, raw):
+        """
+        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.addCallback(self.sendSuccess)
+        d.addErrback(self.sendError, raw)
+        # 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, no client auth here
+            "",  # password is blank, no client auth here
+            self._from_address,
+            recipient.dest.addrstr,
+            StringIO(msg),
+            d,
+            heloFallback=True,
+            requireAuthentication=False,
+            requireTransportSecurity=True)
+        factory.domain = bytes('leap.mail-' + __version__)
+        emit_async(catalog.SMTP_SEND_MESSAGE_START,
+                   self._from_address, recipient.dest.addrstr)
+        reactor.connectSSL(
+            self._host, self._port, factory,
+            contextFactory=SSLContextFactory(self._cert, self._key))
+
+    def _maybe_encrypt_and_sign(self, raw, recipient, fetch_remote=True):
+        """
+        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
+
+        :return: A Deferred that will be fired with a MIMEMultipart message
+                 and the original recipient Message
+        :rtype: Deferred
+        """
+        # pass if the original message's content-type is "multipart/encrypted"
+        origmsg = Parser().parsestr(raw)
+
+        if origmsg.get_content_type() == 'multipart/encrypted':
+            return defer.succeed((origmsg, recipient))
+
+        from_address = validate_address(self._from_address)
+        username, domain = from_address.split('@')
+        to_address = validate_address(recipient.dest.addrstr)
+
+        def maybe_encrypt_and_sign(message):
+            d = self._encrypt_and_sign(
+                message, to_address, from_address,
+                fetch_remote=fetch_remote)
+            d.addCallbacks(signal_encrypt_sign,
+                           if_key_not_found_send_unencrypted,
+                           errbackArgs=(message,))
+            return d
+
+        def signal_encrypt_sign(newmsg):
+            emit_async(catalog.SMTP_END_ENCRYPT_AND_SIGN,
+                       self._from_address,
+                       "%s,%s" % (self._from_address, to_address))
+            return newmsg, recipient
+
+        def if_key_not_found_send_unencrypted(failure, message):
+            failure.trap(KeyNotFound, KeyAddressMismatch)
+
+            log.msg('Will send unencrypted message to %s.' % to_address)
+            emit_async(catalog.SMTP_START_SIGN, self._from_address, to_address)
+            d = self._sign(message, from_address)
+            d.addCallback(signal_sign)
+            return d
+
+        def signal_sign(newmsg):
+            emit_async(catalog.SMTP_END_SIGN, self._from_address)
+            return newmsg, recipient
+
+        log.msg("Will encrypt the message with %s and sign with %s."
+                % (to_address, from_address))
+        emit_async(catalog.SMTP_START_ENCRYPT_AND_SIGN,
+                   self._from_address,
+                   "%s,%s" % (self._from_address, to_address))
+        d = self._maybe_attach_key(origmsg, from_address, to_address)
+        d.addCallback(maybe_encrypt_and_sign)
+        return d
+
+    def _maybe_attach_key(self, origmsg, from_address, to_address):
+        filename = "%s-email-key.asc" % (from_address,)
+
+        def attach_if_address_hasnt_encrypted(to_key):
+            # if the sign_used flag is true that means that we got an encrypted
+            # email from this address, because we conly check signatures on
+            # encrypted emails. In this case we don't attach.
+            # XXX: this might not be true some time in the future
+            if to_key.sign_used:
+                return origmsg
+            return get_key_and_attach(None)
+
+        def get_key_and_attach(_):
+            d = self._keymanager.get_key(from_address, fetch_remote=False)
+            d.addCallback(attach_key)
+            return d
+
+        def attach_key(from_key):
+            msg = origmsg
+            if not origmsg.is_multipart():
+                msg = MIMEMultipart()
+                for h, v in origmsg.items():
+                    msg.add_header(h, v)
+                msg.attach(MIMEText(origmsg.get_payload()))
+
+            keymsg = MIMEApplication(from_key.key_data, _subtype='pgp-keys',
+                                     _encoder=lambda x: x)
+            keymsg.add_header('content-disposition', 'attachment',
+                              filename=filename)
+            msg.attach(keymsg)
+            return msg
+
+        d = self._keymanager.get_key(to_address, fetch_remote=False)
+        d.addCallbacks(attach_if_address_hasnt_encrypted, get_key_and_attach)
+        d.addErrback(lambda _: origmsg)
+        return d
+
+    def _encrypt_and_sign(self, origmsg, encrypt_address, sign_address,
+                          fetch_remote=True):
+        """
+        Create an RFC 3156 compliang PGP encrypted and signed message using
+        C{encrypt_address} to encrypt and C{sign_address} to sign.
+
+        :param origmsg: The original message
+        :type origmsg: email.message.Message
+        :param encrypt_address: The address used to encrypt the message.
+        :type encrypt_address: str
+        :param sign_address: The address used to sign the message.
+        :type sign_address: str
+
+        :return: A Deferred with the MultipartEncrypted message
+        :rtype: Deferred
+        """
+        # create new multipart/encrypted message with 'pgp-encrypted' protocol
+
+        def encrypt(res):
+            newmsg, origmsg = res
+            d = self._keymanager.encrypt(
+                origmsg.as_string(unixfrom=False),
+                encrypt_address, sign=sign_address,
+                fetch_remote=fetch_remote)
+            d.addCallback(lambda encstr: (newmsg, encstr))
+            return d
+
+        def create_encrypted_message(res):
+            newmsg, encstr = res
+            encmsg = MIMEApplication(
+                encstr, _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
+
+        d = self._fix_headers(
+            origmsg,
+            MultipartEncrypted('application/pgp-encrypted'),
+            sign_address)
+        d.addCallback(encrypt)
+        d.addCallback(create_encrypted_message)
+        return d
+
+    def _sign(self, origmsg, sign_address):
+        """
+        Create an RFC 3156 compliant PGP signed MIME message using
+        C{sign_address}.
+
+        :param origmsg: The original message
+        :type origmsg: email.message.Message
+        :param sign_address: The address used to sign the message.
+        :type sign_address: str
+
+        :return: A Deferred with the MultipartSigned message.
+        :rtype: Deferred
+        """
+        # 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"
+
+        def create_signed_message(res):
+            (msg, _), signature = res
+            sigmsg = PGPSignature(signature)
+            # attach original message and signature to new message
+            msg.attach(origmsg)
+            msg.attach(sigmsg)
+            return msg
+
+        dh = self._fix_headers(
+            origmsg,
+            MultipartSigned('application/pgp-signature', 'pgp-sha512'),
+            sign_address)
+        ds = self._keymanager.sign(
+            msgtext, sign_address, digest_algo='SHA512',
+            clearsign=False, detach=True, binary=False)
+        d = defer.gatherResults([dh, ds])
+        d.addCallback(create_signed_message)
+        return d
+
+    def _fix_headers(self, msg, newmsg, sign_address):
+        """
+        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 msg: The original message.
+        :type msg: email.message.Message
+        :param newmsg: The new message being created.
+        :type newmsg: email.message.Message
+        :param sign_address: The address used to sign C{newmsg}
+        :type sign_address: str
+
+        :return: A Deferred with a touple:
+                 (new Message with the unencrypted headers,
+                  original Message with headers removed)
+        :rtype: Deferred
+        """
+        origmsg = deepcopy(msg)
+        # 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())
+        # delete user-agent from origmsg
+        del (origmsg['user-agent'])
+
+        def add_openpgp_header(signkey):
+            username, domain = sign_address.split('@')
+            newmsg.add_header(
+                'OpenPGP', 'id=%s' % signkey.fingerprint,
+                url='https://%s/key/%s' % (domain, username),
+                preference='signencrypt')
+            return newmsg, origmsg
+
+        d = self._keymanager.get_key(sign_address, private=True)
+        d.addCallback(add_openpgp_header)
+        return d
diff --git a/src/leap/bitmask/mail/outgoing/tests/test_outgoing.py b/src/leap/bitmask/mail/outgoing/tests/test_outgoing.py
new file mode 100644
index 00000000..dd053c15
--- /dev/null
+++ b/src/leap/bitmask/mail/outgoing/tests/test_outgoing.py
@@ -0,0 +1,263 @@
+# -*- 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 copy import deepcopy
+from StringIO import StringIO
+from email.parser import Parser
+from datetime import datetime
+from twisted.internet.defer import fail
+from twisted.mail.smtp import User
+from twisted.python import log
+
+from mock import Mock
+
+from leap.mail.rfc3156 import RFC3156CompliantGenerator
+from leap.mail.outgoing.service import OutgoingMail
+from leap.mail.testing import ADDRESS, ADDRESS_2, PUBLIC_KEY_2
+from leap.mail.testing import KeyManagerWithSoledadTestCase
+from leap.mail.testing.smtp import getSMTPFactory
+from leap.keymanager import errors
+
+
+BEGIN_PUBLIC_KEY = "-----BEGIN PGP PUBLIC KEY BLOCK-----"
+
+TEST_USER = u'anotheruser@leap.se'
+
+
+class TestOutgoingMail(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):
+        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.expected_body = '\r\n'.join(self.EMAIL_DATA[9:12]) + "\r\n"
+        self.fromAddr = ADDRESS_2
+
+        class opts:
+            cert = u'/tmp/cert'
+            key = u'/tmp/cert'
+            hostname = 'remote'
+            port = 666
+        self.opts = opts
+
+        def init_outgoing_and_proto(_):
+            self.outgoing_mail = OutgoingMail(
+                self.fromAddr, self.km, opts.cert,
+                opts.key, opts.hostname, opts.port)
+
+            user = TEST_USER
+
+            # TODO -- this shouldn't need SMTP to be tested!? or does it?
+            self.proto = getSMTPFactory(
+                {user: None}, {user: self.km}, {user: None})
+            self.dest = User(ADDRESS, 'gateway.leap.se', self.proto, ADDRESS_2)
+
+        d = KeyManagerWithSoledadTestCase.setUp(self)
+        d.addCallback(init_outgoing_and_proto)
+        return d
+
+    def test_message_encrypt(self):
+        """
+        Test if message gets encrypted to destination email.
+        """
+        def check_decryption(res):
+            decrypted, _ = res
+            self.assertEqual(
+                '\n' + self.expected_body,
+                decrypted,
+                'Decrypted text differs from plaintext.')
+
+        d = self._set_sign_used(ADDRESS)
+        d.addCallback(
+            lambda _:
+            self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest))
+        d.addCallback(self._assert_encrypted)
+        d.addCallback(lambda message: self.km.decrypt(
+            message.get_payload(1).get_payload(), ADDRESS))
+        d.addCallback(check_decryption)
+        return d
+
+    def test_message_encrypt_sign(self):
+        """
+        Test if message gets encrypted to destination email and signed with
+        sender key.
+        '"""
+        def check_decryption_and_verify(res):
+            decrypted, signkey = res
+            self.assertEqual(
+                '\n' + self.expected_body,
+                decrypted,
+                'Decrypted text differs from plaintext.')
+            self.assertTrue(ADDRESS_2 in signkey.address,
+                            "Verification failed")
+
+        d = self._set_sign_used(ADDRESS)
+        d.addCallback(
+            lambda _:
+            self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest))
+        d.addCallback(self._assert_encrypted)
+        d.addCallback(lambda message: self.km.decrypt(
+            message.get_payload(1).get_payload(), ADDRESS, verify=ADDRESS_2))
+        d.addCallback(check_decryption_and_verify)
+        return d
+
+    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=fail(errors.KeyNotFound()))
+        recipient = User('ihavenopubkey@nonleap.se',
+                         'gateway.leap.se', self.proto, ADDRESS)
+        self.outgoing_mail = OutgoingMail(
+            self.fromAddr, self.km, self.opts.cert, self.opts.key,
+            self.opts.hostname, self.opts.port)
+
+        def check_signed(res):
+            message, _ = res
+            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
+            body = (message.get_payload(0)
+                           .get_payload(0)
+                           .get_payload(decode=True))
+            self.assertEqual(self.expected_body,
+                             body)
+            # 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.')
+            return message
+
+        def verify(message):
+            # replace EOL before verifying (according to rfc3156)
+            fp = StringIO()
+            g = RFC3156CompliantGenerator(
+                fp, mangle_from_=False, maxheaderlen=76)
+            g.flatten(message.get_payload(0))
+            signed_text = re.sub('\r?\n', '\r\n',
+                                 fp.getvalue())
+
+            def assert_verify(key):
+                self.assertTrue(ADDRESS_2 in key.address,
+                                'Signature could not be verified.')
+
+            d = self.km.verify(
+                signed_text, ADDRESS_2,
+                detached_sig=message.get_payload(1).get_payload())
+            d.addCallback(assert_verify)
+            return d
+
+        d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, recipient)
+        d.addCallback(check_signed)
+        d.addCallback(verify)
+        return d
+
+    def test_attach_key(self):
+        d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
+        d.addCallback(self._assert_encrypted)
+        d.addCallback(self._check_headers, self.lines[:4])
+        d.addCallback(lambda message: self.km.decrypt(
+            message.get_payload(1).get_payload(), ADDRESS))
+        d.addCallback(lambda (decrypted, _):
+                      self._check_key_attachment(Parser().parsestr(decrypted)))
+        return d
+
+    def test_attach_key_not_known(self):
+        unknown_address = "someunknownaddress@somewhere.com"
+        lines = deepcopy(self.lines)
+        lines[1] = "To: <%s>" % (unknown_address,)
+        raw = '\r\n'.join(lines)
+        dest = User(unknown_address, 'gateway.leap.se', self.proto, ADDRESS_2)
+
+        d = self.outgoing_mail._maybe_encrypt_and_sign(
+                raw, dest, fetch_remote=False)
+        d.addCallback(lambda (message, _):
+                      self._check_headers(message, lines[:4]))
+        d.addCallback(self._check_key_attachment)
+        d.addErrback(log.err)
+        return d
+
+    def _check_headers(self, message, headers):
+        msgstr = message.as_string(unixfrom=False)
+        for header in headers:
+            self.assertTrue(header in msgstr,
+                            "Missing header: %s" % (header,))
+        return message
+
+    def _check_key_attachment(self, message):
+        for payload in message.get_payload():
+            if payload.is_multipart():
+                return self._check_key_attachment(payload)
+            if 'application/pgp-keys' == payload.get_content_type():
+                keylines = PUBLIC_KEY_2.split('\n')
+                key = BEGIN_PUBLIC_KEY + '\n\n' + '\n'.join(keylines[4:-1])
+                self.assertTrue(key in payload.get_payload(decode=True),
+                                "Key attachment don't match")
+                return
+        self.fail("No public key attachment found")
+
+    def _set_sign_used(self, address):
+        def set_sign(key):
+            key.sign_used = True
+            return self.km.put_key(key)
+
+        d = self.km.get_key(address, fetch_remote=False)
+        d.addCallback(set_sign)
+        return d
+
+    def _assert_encrypted(self, res):
+        message, _ = res
+        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())
+        return message