Merge remote-tracking branch 'drebs/feature/3637_use-tls-wrapper-mode' into develop

9 files changed, 185 insertions, 33 deletions

diff --git a/changes/feature_3637-use-tls-wrapper-mode b/changes/feature_3637-use-tls-wrapper-mode
new file mode 100644
index 0000000..668015f
--- /dev/null
+++ b/changes/feature_3637-use-tls-wrapper-mode
@@ -0,0 +1 @@
+  o Use TLS wrapper mode instead of STARTTLS. Closes #3637.
diff --git a/setup.py b/setup.py
index f423f7b..57a4164 100644
--- a/setup.py
+++ b/setup.py
@@ -64,7 +64,7 @@ setup(
     namespace_packages=["leap"],
     package_dir={'': 'src'},
     packages=find_packages('src'),
-    test_suite='leap.mail.load_tests',
+    test_suite='leap.mail.load_tests.load_tests',
     install_requires=utils.parse_requirements(),
     tests_require=utils.parse_requirements(
         reqfiles=['pkg/requirements-testing.pip']),
diff --git a/src/leap/mail/__init__.py b/src/leap/mail/__init__.py
index 5b5ba9b..4b25fe6 100644
--- a/src/leap/mail/__init__.py
+++ b/src/leap/mail/__init__.py
@@ -17,17 +17,10 @@
 
 
 """
-Provide function for loading tests.
+Client mail bits.
 """
 
 
-# Do not force the unittest dependency
-# import unittest
-
-
-# def load_tests():
-#     return unittest.defaultTestLoader.discover('./src/leap/mail')
-
 from ._version import get_versions
 __version__ = get_versions()['version']
 del get_versions
diff --git a/src/leap/mail/load_tests.py b/src/leap/mail/load_tests.py
new file mode 100644
index 0000000..ee89fcc
--- /dev/null
+++ b/src/leap/mail/load_tests.py
@@ -0,0 +1,32 @@
+# -*- coding: utf-8 -*-
+# tests.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/>.
+
+
+"""
+Provide a function for loading tests.
+"""
+
+import unittest
+
+
+def load_tests():
+    suite = unittest.TestSuite()
+    for test in unittest.defaultTestLoader.discover(
+            './src/leap/mail/',
+            top_level_dir='./src/'):
+        suite.addTest(test)
+    return suite
diff --git a/src/leap/mail/smtp/smtprelay.py b/src/leap/mail/smtp/smtprelay.py
index d9bbbf9..fca66c0 100644
--- a/src/leap/mail/smtp/smtprelay.py
+++ b/src/leap/mail/smtp/smtprelay.py
@@ -17,6 +17,20 @@
 
 """
 LEAP SMTP encrypted relay.
+
+The following classes comprise the SMTP relay 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.
+    * SSLContextFactory - Contains the relevant ssl information for the
+      connection.
+    * EncryptedMessage - An implementation of twisted.mail.smtp.IMessage that
+      knows how to encrypt/sign itself before sending.
+
+
 """
 
 import re
@@ -173,7 +187,6 @@ class SMTPFactory(ServerFactory):
         @return: The protocol.
         @rtype: SMTPDelivery
         """
-        # If needed, we might use ESMTPDelivery here instead.
         smtpProtocol = smtp.SMTP(SMTPDelivery(self._km, self._config))
         smtpProtocol.factory = self
         return smtpProtocol
@@ -305,7 +318,7 @@ class SMTPDelivery(object):
 # EncryptedMessage
 #
 
-class CtxFactory(ssl.ClientContextFactory):
+class SSLContextFactory(ssl.ClientContextFactory):
     def __init__(self, cert, key):
         self.cert = cert
         self.key = key
@@ -450,6 +463,8 @@ class EncryptedMessage(object):
                                                      self._config[PORT_KEY]))
 
         d = defer.Deferred()
+        # we don't pass an ssl context factory to the ESMTPSenderFactory
+        # because ssl will be handled by reactor.connectSSL() below.
         factory = smtp.ESMTPSenderFactory(
             "",  # username is blank because server does not use auth.
             "",  # password is blank because server does not use auth.
@@ -457,15 +472,15 @@ class EncryptedMessage(object):
             self._user.dest.addrstr,
             StringIO(msg),
             d,
-            contextFactory=CtxFactory(self._config[CERT_KEY],
-                                      self._config[KEY_KEY]),
-            requireAuthentication=False)
+            requireAuthentication=False,
+            requireTransportSecurity=True)
         signal(proto.SMTP_SEND_MESSAGE_START, self._user.dest.addrstr)
-        reactor.connectTCP(
+        reactor.connectSSL(
             self._config[HOST_KEY],
             self._config[PORT_KEY],
-            factory
-        )
+            factory,
+            contextFactory=SSLContextFactory(self._config[CERT_KEY],
+                                             self._config[KEY_KEY]))
         d.addCallback(self.sendSuccess)
         d.addErrback(self.sendError)
         return d
diff --git a/src/leap/mail/smtp/tests/__init__.py b/src/leap/mail/smtp/tests/__init__.py
index 7fed7da..9b54de3 100644
--- a/src/leap/mail/smtp/tests/__init__.py
+++ b/src/leap/mail/smtp/tests/__init__.py
@@ -113,8 +113,8 @@ class TestCaseWithKeyManager(BaseLeapTest):
             'username': address,
             'password': '<password>',
             'encrypted_only': True,
-            'cert': 'blah',
-            'key': 'bleh',
+            'cert': 'src/leap/mail/smtp/tests/cert/server.crt',
+            'key': 'src/leap/mail/smtp/tests/cert/server.key',
         }
 
         class Response(object):
diff --git a/src/leap/mail/smtp/tests/cert/server.crt b/src/leap/mail/smtp/tests/cert/server.crt
new file mode 100644
index 0000000..a27391c
--- /dev/null
+++ b/src/leap/mail/smtp/tests/cert/server.crt
@@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/src/leap/mail/smtp/tests/cert/server.key b/src/leap/mail/smtp/tests/cert/server.key
new file mode 100644
index 0000000..197a449
--- /dev/null
+++ b/src/leap/mail/smtp/tests/cert/server.key
@@ -0,0 +1,51 @@
+-----BEGIN RSA PRIVATE KEY-----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-----END RSA PRIVATE KEY-----
diff --git a/src/leap/mail/smtp/tests/test_smtprelay.py b/src/leap/mail/smtp/tests/test_smtprelay.py
index a529c93..7fefe77 100644
--- a/src/leap/mail/smtp/tests/test_smtprelay.py
+++ b/src/leap/mail/smtp/tests/test_smtprelay.py
@@ -23,8 +23,8 @@ SMTP relay tests.
 
 import re
 
-
 from datetime import datetime
+from gnupg._util import _make_binary_stream
 from twisted.test import proto_helpers
 from twisted.mail.smtp import (
     User,
@@ -33,7 +33,6 @@ from twisted.mail.smtp import (
 )
 from mock import Mock
 
-
 from leap.mail.smtp.smtprelay import (
     SMTPFactory,
     EncryptedMessage,
@@ -45,7 +44,6 @@ from leap.mail.smtp.tests import (
 )
 from leap.keymanager import openpgp
 
-
 # some regexps
 IP_REGEX = "(([0-9]|[1-9][0-9]|1[0-9]{2}|2[0-4][0-9]|25[0-5])\.){3}" + \
     "([0-9]|[1-9][0-9]|1[0-9]{2}|2[0-4][0-9]|25[0-5])"
@@ -127,11 +125,22 @@ class TestSmtpRelay(TestCaseWithKeyManager):
         for line in self.EMAIL_DATA[4:12]:
             m.lineReceived(line)
         m.eomReceived()
+        # assert structure of encrypted message
+        self.assertTrue('Content-Type' in m._msg)
+        self.assertEqual('multipart/encrypted', m._msg.get_content_type())
+        self.assertEqual('application/pgp-encrypted',
+                         m._msg.get_param('protocol'))
+        self.assertEqual(2, len(m._msg.get_payload()))
+        self.assertEqual('application/pgp-encrypted',
+                         m._msg.get_payload(0).get_content_type())
+        self.assertEqual('application/octet-stream',
+                         m._msg.get_payload(1).get_content_type())
         privkey = self._km.get_key(
             ADDRESS, openpgp.OpenPGPKey, private=True)
-        decrypted = self._km.decrypt(m._message.get_payload(), privkey)
+        decrypted = self._km.decrypt(
+            m._msg.get_payload(1).get_payload(), privkey)
         self.assertEqual(
-            '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n',
+            '\n' + '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n',
             decrypted,
             'Decrypted text differs from plaintext.')
 
@@ -149,14 +158,24 @@ class TestSmtpRelay(TestCaseWithKeyManager):
             m.lineReceived(line)
         # trigger encryption and signing
         m.eomReceived()
+        # assert structure of encrypted message
+        self.assertTrue('Content-Type' in m._msg)
+        self.assertEqual('multipart/encrypted', m._msg.get_content_type())
+        self.assertEqual('application/pgp-encrypted',
+                         m._msg.get_param('protocol'))
+        self.assertEqual(2, len(m._msg.get_payload()))
+        self.assertEqual('application/pgp-encrypted',
+                         m._msg.get_payload(0).get_content_type())
+        self.assertEqual('application/octet-stream',
+                         m._msg.get_payload(1).get_content_type())
         # decrypt and verify
         privkey = self._km.get_key(
             ADDRESS, openpgp.OpenPGPKey, private=True)
         pubkey = self._km.get_key(ADDRESS_2, openpgp.OpenPGPKey)
         decrypted = self._km.decrypt(
-            m._message.get_payload(), privkey, verify=pubkey)
+            m._msg.get_payload(1).get_payload(), privkey, verify=pubkey)
         self.assertEqual(
-            '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n',
+            '\n' + '\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n',
             decrypted,
             'Decrypted text differs from plaintext.')
 
@@ -175,22 +194,34 @@ class TestSmtpRelay(TestCaseWithKeyManager):
             m.lineReceived(line)
         # trigger signing
         m.eomReceived()
+        # assert structure of signed message
+        self.assertTrue('Content-Type' in m._msg)
+        self.assertEqual('multipart/signed', m._msg.get_content_type())
+        self.assertEqual('application/pgp-signature',
+                         m._msg.get_param('protocol'))
+        self.assertEqual('pgp-sha512', m._msg.get_param('micalg'))
         # assert content of message
+        self.assertEqual(
+            m._msg.get_payload(0).get_payload(decode=True),
+            '\r\n'.join(self.EMAIL_DATA[9:13]))
+        # assert content of signature
         self.assertTrue(
-            m._message.get_payload().startswith(
-                '-----BEGIN PGP SIGNED MESSAGE-----\n' +
-                'Hash: SHA1\n\n' + 
-                ('\r\n'.join(self.EMAIL_DATA[9:12]) + '\r\n' +
-                '-----BEGIN PGP SIGNATURE-----\n')),
+            m._msg.get_payload(1).get_payload().startswith(
+                '-----BEGIN PGP SIGNATURE-----\n'),
             'Message does not start with signature header.')
         self.assertTrue(
-            m._message.get_payload().endswith(
+            m._msg.get_payload(1).get_payload().endswith(
                 '-----END PGP SIGNATURE-----\n'),
             'Message does not end with signature footer.')
         # assert signature is valid
         pubkey = self._km.get_key(ADDRESS_2, openpgp.OpenPGPKey)
+        # replace EOL before verifying (according to rfc3156)
+        signed_text = re.sub('\r?\n', '\r\n',
+                             m._msg.get_payload(0).as_string())
         self.assertTrue(
-            self._km.verify(m._message.get_payload(), pubkey),
+            self._km.verify(signed_text,
+                            pubkey,
+                            detached_sig=m._msg.get_payload(1).get_payload()),
             'Signature could not be verified.')
 
     def test_missing_key_rejects_address(self):