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authorKali Kaneko <kali@leap.se>2015-01-02 10:58:43 -0400
committerKali Kaneko <kali@leap.se>2015-02-11 14:05:43 -0400
commit4fa3d27225f44d9598d24d9e59a97baaa9bbb90e (patch)
tree148f46cee12badce78819427819a11e0b04096c6 /src/leap/mail/outgoing
parent22f619cf2a295ecc5beff16a91de63728ac4b17d (diff)
make outgoing a new submodule
Diffstat (limited to 'src/leap/mail/outgoing')
-rw-r--r--src/leap/mail/outgoing/__init__.py0
-rw-r--r--src/leap/mail/outgoing/service.py429
-rw-r--r--src/leap/mail/outgoing/tests/__init__.py0
-rw-r--r--src/leap/mail/outgoing/tests/test_outgoing.py187
4 files changed, 616 insertions, 0 deletions
diff --git a/src/leap/mail/outgoing/__init__.py b/src/leap/mail/outgoing/__init__.py
new file mode 100644
index 0000000..e69de29
--- /dev/null
+++ b/src/leap/mail/outgoing/__init__.py
diff --git a/src/leap/mail/outgoing/service.py b/src/leap/mail/outgoing/service.py
new file mode 100644
index 0000000..b70b3b1
--- /dev/null
+++ b/src/leap/mail/outgoing/service.py
@@ -0,0 +1,429 @@
+# -*- 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/>.
+import re
+from StringIO import StringIO
+from email.parser import Parser
+from email.mime.application import MIMEApplication
+
+from OpenSSL import SSL
+
+from twisted.mail import smtp
+from twisted.internet import reactor
+from twisted.internet import defer
+from twisted.protocols.amp import ssl
+from twisted.python import log
+
+from leap.common.check import leap_assert_type, leap_assert
+from leap.common.events import proto, signal
+from leap.keymanager import KeyManager
+from leap.keymanager.openpgp import OpenPGPKey
+from leap.keymanager.errors import KeyNotFound
+from leap.mail import __version__
+from leap.mail.utils import validate_address
+from leap.mail.smtp.rfc3156 import MultipartEncrypted
+from leap.mail.smtp.rfc3156 import MultipartSigned
+from leap.mail.smtp.rfc3156 import encode_base64_rec
+from leap.mail.smtp.rfc3156 import RFC3156CompliantGenerator
+from leap.mail.smtp.rfc3156 import PGPSignature
+from leap.mail.smtp.rfc3156 import PGPEncrypted
+
+# 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
+
+
+class OutgoingMail:
+ """
+ A service for handling encrypted outgoing mail.
+ """
+
+ FOOTER_STRING = "I prefer encrypted email"
+
+ def __init__(self, from_address, keymanager, cert, key, host, port):
+ """
+ Initialize the mail service.
+
+ :param from_address: The sender address.
+ :type from_address: str
+ :param keymanager: A KeyManager for retrieving recipient's keys.
+ :type keymanager: leap.common.keymanager.KeyManager
+ :param cert: The client certificate for SSL authentication.
+ :type cert: str
+ :param key: The client private key for SSL authentication.
+ :type key: str
+ :param host: The hostname of the remote SMTP server.
+ :type host: str
+ :param port: The port of the remote SMTP server.
+ :type port: int
+ """
+
+ # assert params
+ leap_assert_type(from_address, str)
+ leap_assert('@' in from_address)
+ leap_assert_type(keymanager, KeyManager)
+ leap_assert_type(host, str)
+ leap_assert(host != '')
+ leap_assert_type(port, int)
+ leap_assert(port is not 0)
+ leap_assert_type(cert, unicode)
+ leap_assert(cert != '')
+ leap_assert_type(key, unicode)
+ leap_assert(key != '')
+
+ self._port = port
+ self._host = host
+ self._key = key
+ self._cert = cert
+ self._from_address = from_address
+ self._keymanager = keymanager
+
+ def send_message(self, raw, recipient):
+ """
+ Sends a message to a recipient. Maybe encrypts and signs.
+
+ :param raw: The raw message
+ :type raw: str
+ :param recipient: The recipient for the message
+ :type recipient: smtp.User
+ :return: a deferred which delivers the message when fired
+ """
+ d = self._maybe_encrypt_and_sign(raw, recipient)
+ d.addCallback(self._route_msg)
+ d.addErrback(self.sendError)
+ return d
+
+ def sendSuccess(self, smtp_sender_result):
+ """
+ Callback for a successful send.
+
+ :param smtp_sender_result: The result from the ESMTPSender from
+ _route_msg
+ :type smtp_sender_result: tuple(int, list(tuple))
+ """
+ dest_addrstr = smtp_sender_result[1][0][0]
+ log.msg('Message sent to %s' % dest_addrstr)
+ signal(proto.SMTP_SEND_MESSAGE_SUCCESS, dest_addrstr)
+
+ def sendError(self, failure):
+ """
+ Callback for an unsuccessfull send.
+
+ :param e: The result from the last errback.
+ :type e: anything
+ """
+ # XXX: need to get the address from the exception to send signal
+ # signal(proto.SMTP_SEND_MESSAGE_ERROR, self._user.dest.addrstr)
+ err = failure.value
+ log.err(err)
+ raise err
+
+ def _route_msg(self, encrypt_and_sign_result):
+ """
+ Sends the msg using the ESMTPSenderFactory.
+
+ :param encrypt_and_sign_result: A tuple containing the 'maybe'
+ encrypted message and the recipient
+ :type encrypt_and_sign_result: tuple
+ """
+ message, recipient = encrypt_and_sign_result
+ log.msg("Connecting to SMTP server %s:%s" % (self._host, self._port))
+ msg = message.as_string(False)
+
+ # we construct a defer to pass to the ESMTPSenderFactory
+ d = defer.Deferred()
+ d.addCallbacks(self.sendSuccess, self.sendError)
+ # we don't pass an ssl context factory to the ESMTPSenderFactory
+ # because ssl will be handled by reactor.connectSSL() below.
+ factory = smtp.ESMTPSenderFactory(
+ "", # username is blank because client auth is done on SSL protocol level
+ "", # password is blank because client auth is done on SSL protocol level
+ self._from_address,
+ recipient.dest.addrstr,
+ StringIO(msg),
+ d,
+ heloFallback=True,
+ requireAuthentication=False,
+ requireTransportSecurity=True)
+ factory.domain = __version__
+ signal(proto.SMTP_SEND_MESSAGE_START, recipient.dest.addrstr)
+ reactor.connectSSL(
+ self._host, self._port, factory,
+ contextFactory=SSLContextFactory(self._cert, self._key))
+
+ def _maybe_encrypt_and_sign(self, raw, recipient):
+ """
+ Attempt to encrypt and sign the outgoing message.
+
+ The behaviour of this method depends on:
+
+ 1. the original message's content-type, and
+ 2. the availability of the recipient's public key.
+
+ If the original message's content-type is "multipart/encrypted", then
+ the original message is not altered. For any other content-type, the
+ method attempts to fetch the recipient's public key. If the
+ recipient's public key is available, the message is encrypted and
+ signed; otherwise it is only signed.
+
+ Note that, if the C{encrypted_only} configuration is set to True and
+ the recipient's public key is not available, then the recipient
+ address would have been rejected in SMTPDelivery.validateTo().
+
+ The following table summarizes the overall behaviour of the gateway:
+
+ +---------------------------------------------------+----------------+
+ | content-type | rcpt pubkey | enforce encr. | action |
+ +---------------------+-------------+---------------+----------------+
+ | multipart/encrypted | any | any | pass |
+ | other | available | any | encrypt + sign |
+ | other | unavailable | yes | reject |
+ | other | unavailable | no | sign |
+ +---------------------+-------------+---------------+----------------+
+
+ :param raw: The raw message
+ :type raw: str
+ :param recipient: The recipient for the message
+ :type: recipient: smtp.User
+
+ :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"
+ lines = raw.split('\r\n')
+ origmsg = Parser().parsestr(raw)
+
+ if origmsg.get_content_type() == 'multipart/encrypted':
+ return defer.success((origmsg, recipient))
+
+ from_address = validate_address(self._from_address)
+ username, domain = from_address.split('@')
+ to_address = validate_address(recipient.dest.addrstr)
+
+ # add a nice footer to the outgoing message
+ # XXX: footer will eventually optional or be removed
+ if origmsg.get_content_type() == 'text/plain':
+ lines.append('--')
+ lines.append('%s - https://%s/key/%s' %
+ (self.FOOTER_STRING, domain, username))
+ lines.append('')
+
+ origmsg = Parser().parsestr('\r\n'.join(lines))
+
+ def signal_encrypt_sign(newmsg):
+ signal(proto.SMTP_END_ENCRYPT_AND_SIGN,
+ "%s,%s" % (self._from_address, to_address))
+ return newmsg, recipient
+
+ def signal_sign(newmsg):
+ signal(proto.SMTP_END_SIGN, self._from_address)
+ return newmsg, recipient
+
+ def if_key_not_found_send_unencrypted(failure):
+ if failure.check(KeyNotFound):
+ log.msg('Will send unencrypted message to %s.' % to_address)
+ signal(proto.SMTP_START_SIGN, self._from_address)
+ d = self._sign(origmsg, from_address)
+ d.addCallback(signal_sign)
+ return d
+ else:
+ return failure
+
+ log.msg("Will encrypt the message with %s and sign with %s."
+ % (to_address, from_address))
+ signal(proto.SMTP_START_ENCRYPT_AND_SIGN,
+ "%s,%s" % (self._from_address, to_address))
+ d = self._encrypt_and_sign(origmsg, to_address, from_address)
+ d.addCallbacks(signal_encrypt_sign, if_key_not_found_send_unencrypted)
+ return d
+
+ def _encrypt_and_sign(self, origmsg, encrypt_address, sign_address):
+ """
+ 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, OpenPGPKey, sign=sign_address)
+ 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, OpenPGPKey, 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, origmsg, 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 origmsg: The original message.
+ :type origmsg: 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
+ """
+ # 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.key_id,
+ url='https://%s/key/%s' % (domain, username),
+ preference='signencrypt')
+ return newmsg, origmsg
+
+ d = self._keymanager.get_key(sign_address, OpenPGPKey, private=True)
+ d.addCallback(add_openpgp_header)
+ return d
diff --git a/src/leap/mail/outgoing/tests/__init__.py b/src/leap/mail/outgoing/tests/__init__.py
new file mode 100644
index 0000000..e69de29
--- /dev/null
+++ b/src/leap/mail/outgoing/tests/__init__.py
diff --git a/src/leap/mail/outgoing/tests/test_outgoing.py b/src/leap/mail/outgoing/tests/test_outgoing.py
new file mode 100644
index 0000000..fa50c30
--- /dev/null
+++ b/src/leap/mail/outgoing/tests/test_outgoing.py
@@ -0,0 +1,187 @@
+# -*- coding: utf-8 -*-
+# test_gateway.py
+# Copyright (C) 2013 LEAP
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program. If not, see <http://www.gnu.org/licenses/>.
+
+
+"""
+SMTP gateway tests.
+"""
+
+import re
+from datetime import datetime
+from twisted.internet.defer import fail
+from twisted.mail.smtp import User
+
+from mock import Mock
+
+from leap.mail.smtp.gateway import SMTPFactory
+from leap.mail.outgoing.service import OutgoingMail
+from leap.mail.tests import (
+ TestCaseWithKeyManager,
+ ADDRESS,
+ ADDRESS_2,
+)
+from leap.keymanager import openpgp, errors
+
+
+class TestOutgoingMail(TestCaseWithKeyManager):
+ EMAIL_DATA = ['HELO gateway.leap.se',
+ 'MAIL FROM: <%s>' % ADDRESS_2,
+ 'RCPT TO: <%s>' % ADDRESS,
+ 'DATA',
+ 'From: User <%s>' % ADDRESS_2,
+ 'To: Leap <%s>' % ADDRESS,
+ 'Date: ' + datetime.now().strftime('%c'),
+ 'Subject: test message',
+ '',
+ 'This is a secret message.',
+ 'Yours,',
+ 'A.',
+ '',
+ '.',
+ 'QUIT']
+
+ def setUp(self):
+ 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\r\n--\r\nI prefer encrypted email - "
+ "https://leap.se/key/anotheruser\r\n")
+ self.fromAddr = ADDRESS_2
+
+ def init_outgoing_and_proto(_):
+ self.outgoing_mail = OutgoingMail(
+ self.fromAddr, self._km, self._config['cert'],
+ self._config['key'], self._config['host'],
+ self._config['port'])
+ self.proto = SMTPFactory(
+ u'anotheruser@leap.se',
+ self._km,
+ self._config['encrypted_only'],
+ self.outgoing_mail).buildProtocol(('127.0.0.1', 0))
+ self.dest = User(ADDRESS, 'gateway.leap.se', self.proto, ADDRESS)
+
+ d = TestCaseWithKeyManager.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.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, openpgp.OpenPGPKey))
+ 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.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, openpgp.OpenPGPKey,
+ 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._config['cert'], self._config['key'],
+ self._config['host'], self._config['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
+ self.assertEqual(self.expected_body,
+ message.get_payload(0).get_payload(decode=True))
+ # assert content of signature
+ self.assertTrue(
+ message.get_payload(1).get_payload().startswith(
+ '-----BEGIN PGP SIGNATURE-----\n'),
+ 'Message does not start with signature header.')
+ self.assertTrue(
+ message.get_payload(1).get_payload().endswith(
+ '-----END PGP SIGNATURE-----\n'),
+ 'Message does not end with signature footer.')
+ return message
+
+ def verify(message):
+ # replace EOL before verifying (according to rfc3156)
+ signed_text = re.sub('\r?\n', '\r\n',
+ message.get_payload(0).as_string())
+
+ def assert_verify(key):
+ self.assertTrue(ADDRESS_2 in key.address,
+ 'Signature could not be verified.')
+
+ d = self._km.verify(
+ signed_text, ADDRESS_2, openpgp.OpenPGPKey,
+ 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 _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