4 files changed, 127 insertions, 16 deletions
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-----
+MIIFBjCCAu4CCQCWn3oMoQrDJTANBgkqhkiG9w0BAQUFADBFMQswCQYDVQQGEwJV
+UzETMBEGA1UECAwKU29tZS1TdGF0ZTEhMB8GA1UECgwYSW50ZXJuZXQgV2lkZ2l0
+cyBQdHkgTHRkMB4XDTEzMTAyMzE0NDUwNFoXDTE2MDcxOTE0NDUwNFowRTELMAkG
+A1UEBhMCVVMxEzARBgNVBAgMClNvbWUtU3RhdGUxITAfBgNVBAoMGEludGVybmV0
+IFdpZGdpdHMgUHR5IEx0ZDCCAiIwDQYJKoZIhvcNAQEBBQADggIPADCCAgoCggIB
+APexTvEvG7cSmZdAERHt9TB11cSor54Y/F7NmYMdSOJNi4Y0kwkSslpdfipi+mt/
+NFg/uGKi1mcgvuXdVbVPZ9rCgVpIzMncO8RAP7a5+I2zKUzqMCCbLH16sYpo/rDk
+VQ5V15TwLsTzOFGG8Cgp68TR8zHuZ4Edf2zMGC1IaiJ6W38LTnJgsowYOCFDAF3z
+L36kxMO5gNGEUYV6tjltx+rAcXka3po+xiAgvW6q65UUgDHcIdEGG2dc9bkxxPl7
+RkprF2RwwADNzYS7Tn+Hpmjy06pfYZHNME+Iw515bCRF3GQFUU4BpGnY7EO+h4P9
+Kb1h948gUT9/oswXG+q2Kwk8AoggMJkUOWDFiCa5UjW1GBoxxb7VtZ+QTJXxlFWc
+M2VzT7M/HX+P4b05vY4MXJjxPAFKrAGS7J8DKW8WJNUnXa9XSDBHg5qijDzZ/zGm
+HTdG6iADnJLmOHBQgFQ12a/n9mYV2GPVC6FlgDzG9f0/SUPBUCafyWYz1LwKY4VM
+2NLx/iwYMQsNIMSZQfNmufNDBr70+BShe3ZpbmKB/J33d87AuJd2HjnsThTEAAr+
+6CejyYmwFutoDUCF8IaKGJEp7OGP2//ub4nt5WwW8DYLRi8EqtzEnxPo5ZiayHMY
+GHR1jpX1O5JVJFUE79bZCFFHKmtJc4kVZS4m4rTLsk83AgMBAAEwDQYJKoZIhvcN
+AQEFBQADggIBAEt4PIRqVuALQSdgZ+GiZYuvEVjxoDVtMSc/ym93Gi8R7DDivFH9
+4suQc5QUiuEF8lpEtkmh+PZ+oFdQkjhBH80h7p4BUSyBy5Yi6dy7ATTlBAqwzCYZ
+4wzHeJzu1SI6FinZLksoULbcw04n410aGHkLa6I9O3vCC4kXSnBlwU1sUsJphxM2
+3pkHBpvv79XYf5kFqZPzF16aO7rxFuVvqgXLyzwuyP9kH5zMA21Kioxs/pNyg1lm
+5h0VinpHLPse+4tYih1L1WLMpEZiSwZgFhoRtlcdIVXokZPaX4G2EkdrMmSQruWg
+Uz8Av6LEYHmRfbYwYM2kEX/+AF8thpTQDbvxjqYk5oyGX4wpKGpih1ac/jYu3O8B
+VLhbxZlBYcLxCqqNsGJrWaiHj2Jf4GhUB0O9hXfaZDMqEGXT9GzOz0yF6b3pDQVy
+H0lKIBb+kQzB/jhZKu4vrTAowXtt/av5d7D+rpAU1SxfUhBOPNSRoJUI5NSBbokp
+a7u4azdB2IQETX3d2rhDk09EbG1XmMi5Vg1oa8nxfMOWXZnDMusJoZClKjrthmwd
+rtR5et44XYhX6p217RBkYMDOVFT7aZpu4SaFeqZIuarVYodSmgXToOFXPsrLppRQ
+adOT0FpU64RPNrQz5NF1bSIjqrHSaRVacf8yr7qqxNnpMsrtkDJzsMBz
+-----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):