[tests] add test to validate signature from apple mail

This change adds test to validate signature of encrypted email created
by apple mail. It's important to note that apple mail has a specific way
to encrypt signed messages. First it sign the email and then encrypt the
previous signed message. It was also added a message file with the
expected data.

3 files changed, 87 insertions, 4 deletions

diff --git a/mail/src/leap/mail/incoming/service.py b/mail/src/leap/mail/incoming/service.py
index f60921aa..bf850b57 100644
--- a/mail/src/leap/mail/incoming/service.py
+++ b/mail/src/leap/mail/incoming/service.py
@@ -458,10 +458,8 @@ class IncomingMail(Service):
                     self.LEAP_SIGNATURE_HEADER,
                     self.LEAP_SIGNATURE_INVALID)
             else:
-                decrmsg.add_header(
-                    self.LEAP_SIGNATURE_HEADER,
-                    self.LEAP_SIGNATURE_VALID,
-                    pubkey=signkey.fingerprint)
+                self._add_verified_signature_header(decrmsg,
+                                                    signkey.fingerprint)
             return decrmsg.as_string()
 
         if msg.get_content_type() == MULTIPART_ENCRYPTED:
@@ -475,6 +473,12 @@ class IncomingMail(Service):
         d.addCallback(add_leap_header)
         return d
 
+    def _add_verified_signature_header(self, decrmsg, fingerprint):
+        decrmsg.add_header(
+            self.LEAP_SIGNATURE_HEADER,
+            self.LEAP_SIGNATURE_VALID,
+            pubkey=fingerprint)
+
     def _add_decrypted_header(self, msg):
         msg.add_header(self.LEAP_ENCRYPTION_HEADER,
                        self.LEAP_ENCRYPTION_DECRYPTED)
diff --git a/mail/src/leap/mail/incoming/tests/rfc822.multi-encrypt-signed.message b/mail/src/leap/mail/incoming/tests/rfc822.multi-encrypt-signed.message
new file mode 100644
index 00000000..98304f24
--- /dev/null
+++ b/mail/src/leap/mail/incoming/tests/rfc822.multi-encrypt-signed.message
@@ -0,0 +1,61 @@
+Content-Type: multipart/encrypted;
+    boundary="Apple-Mail=_C01A1464-6C43-43BF-8F62-157335B7E25B";
+    protocol="application/pgp-encrypted";
+Subject: Enc signed
+Mime-Version: 1.0 (Mac OS X Mail 9.3 \(3124\))
+From: Leap Test Key <leap@leap.se>
+Date: Tue, 24 May 2016 11:47:24 -0300
+Content-Description: OpenPGP encrypted message
+To: leap@leap.se
+
+This is an OpenPGP/MIME encrypted message (RFC 2440 and 3156)
+--Apple-Mail=_C01A1464-6C43-43BF-8F62-157335B7E25B
+Content-Type: application/pgp-encrypted
+Content-Description: PGP/MIME Versions Identification
+
+--Apple-Mail=_C01A1464-6C43-43BF-8F62-157335B7E25B
+Content-Disposition: inline;
+    filename=encrypted.asc
+Content-Type: application/octet-stream;
+    name=encrypted.asc
+Content-Description: OpenPGP encrypted message
+
+-----BEGIN PGP MESSAGE-----
+Version: GnuPG v2
+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tEyc
+-----END PGP MESSAGE-----
+
+--Apple-Mail=_C01A1464-6C43-43BF-8F62-157335B7E25B--
\ No newline at end of file
diff --git a/mail/src/leap/mail/incoming/tests/test_incoming_mail.py b/mail/src/leap/mail/incoming/tests/test_incoming_mail.py
index 754df9f0..91f25566 100644
--- a/mail/src/leap/mail/incoming/tests/test_incoming_mail.py
+++ b/mail/src/leap/mail/incoming/tests/test_incoming_mail.py
@@ -22,6 +22,7 @@ Test case for leap.mail.incoming.service
 @license: GPLv3, see included LICENSE file
 """
 
+import os
 import json
 
 from email.mime.application import MIMEApplication
@@ -295,6 +296,23 @@ subject: independence of cyberspace
             self._do_fetch(message.as_string()))
         return d
 
+    def testValidateSignatureFromEncryptedEmailFromAppleMail(self):
+        CURRENT_PATH = os.path.split(os.path.abspath(__file__))[0]
+        enc_signed_file = os.path.join(CURRENT_PATH,
+                                       'rfc822.multi-encrypt-signed.message')
+        self.fetcher._add_verified_signature_header = Mock()
+
+        def add_verified_signature_header_called(_):
+            self.assertTrue(self.fetcher._add_verified_signature_header.called,
+                            "There was some errors verifying signature")
+
+        with open(enc_signed_file) as f:
+            enc_signed_raw = f.read()
+
+        d = self._do_fetch(enc_signed_raw)
+        d.addCallback(add_verified_signature_header_called)
+        return d
+
     def testListener(self):
         self.called = False