Attach key for addresses without known key

This seems to fix the problem with some headers dissapearing (#6692)

2 files changed, 72 insertions, 39 deletions

diff --git a/src/leap/mail/outgoing/service.py b/src/leap/mail/outgoing/service.py
index 9777187..c881830 100644
--- a/src/leap/mail/outgoing/service.py
+++ b/src/leap/mail/outgoing/service.py
@@ -16,6 +16,7 @@
 # along with this program. If not, see <http://www.gnu.org/licenses/>.
 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
@@ -33,7 +34,7 @@ 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.keymanager.errors import KeyNotFound, KeyAddressMismatch
 from leap.mail import __version__
 from leap.mail.utils import validate_address
 from leap.mail.smtp.rfc3156 import MultipartEncrypted
@@ -229,32 +230,37 @@ class OutgoingMail:
         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)
+            d.addCallbacks(signal_encrypt_sign,
+                           if_key_not_found_send_unencrypted,
+                           errbackArgs=(message,))
+            return d
+
         def signal_encrypt_sign(newmsg):
             signal(proto.SMTP_END_ENCRYPT_AND_SIGN,
                    "%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)
+            signal(proto.SMTP_START_SIGN, self._from_address)
+            d = self._sign(message, from_address)
+            d.addCallback(signal_sign)
+            return d
+
         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._maybe_attach_key(origmsg, from_address, to_address)
-        d.addCallback(self._encrypt_and_sign, to_address, from_address)
-        d.addCallbacks(signal_encrypt_sign, if_key_not_found_send_unencrypted)
+        d.addCallback(maybe_encrypt_and_sign)
         return d
 
     def _maybe_attach_key(self, origmsg, from_address, to_address):
@@ -267,7 +273,9 @@ class OutgoingMail:
             # 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, OpenPGPKey,
                                          fetch_remote=False)
             d.addCallback(attach_key)
@@ -290,7 +298,7 @@ class OutgoingMail:
 
         d = self._keymanager.get_key(to_address, OpenPGPKey,
                                      fetch_remote=False)
-        d.addCallback(attach_if_address_hasnt_encrypted)
+        d.addCallbacks(attach_if_address_hasnt_encrypted, get_key_and_attach)
         d.addErrback(lambda _: origmsg)
         return d
 
@@ -386,7 +394,7 @@ class OutgoingMail:
         d.addCallback(create_signed_message)
         return d
 
-    def _fix_headers(self, origmsg, newmsg, sign_address):
+    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}.
@@ -416,8 +424,8 @@ class OutgoingMail:
 
             - User-Agent
 
-        :param origmsg: The original message.
-        :type origmsg: email.message.Message
+        :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}
@@ -428,6 +436,7 @@ class OutgoingMail:
                   original Message with headers removed)
         :rtype: Deferred
         """
+        origmsg = deepcopy(msg)
         # move headers from origmsg to newmsg
         headers = origmsg.items()
         passthrough = [
diff --git a/src/leap/mail/outgoing/tests/test_outgoing.py b/src/leap/mail/outgoing/tests/test_outgoing.py
index 0eb05c8..2376da9 100644
--- a/src/leap/mail/outgoing/tests/test_outgoing.py
+++ b/src/leap/mail/outgoing/tests/test_outgoing.py
@@ -21,6 +21,7 @@ SMTP gateway tests.
 """
 
 import re
+from StringIO import StringIO
 from email.parser import Parser
 from datetime import datetime
 from twisted.internet.defer import fail
@@ -29,6 +30,7 @@ from twisted.mail.smtp import User
 from mock import Mock
 
 from leap.mail.smtp.gateway import SMTPFactory
+from leap.mail.smtp.rfc3156 import RFC3156CompliantGenerator
 from leap.mail.outgoing.service import OutgoingMail
 from leap.mail.tests import (
     TestCaseWithKeyManager,
@@ -149,8 +151,11 @@ class TestOutgoingMail(TestCaseWithKeyManager):
                              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,
-                             message.get_payload(0).get_payload(decode=True))
+                             body)
             # assert content of signature
             self.assertTrue(
                 message.get_payload(1).get_payload().startswith(
@@ -164,8 +169,12 @@ class TestOutgoingMail(TestCaseWithKeyManager):
 
         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',
-                                 message.get_payload(0).as_string())
+                                 fp.getvalue())
 
             def assert_verify(key):
                 self.assertTrue(ADDRESS_2 in key.address,
@@ -183,32 +192,47 @@ class TestOutgoingMail(TestCaseWithKeyManager):
         return d
 
     def test_attach_key(self):
-        def check_headers(message):
-            msgstr = message.as_string(unixfrom=False)
-            for header in self.EMAIL_DATA[4:8]:
-                self.assertTrue(header in msgstr,
-                                "Missing header: %s" % (header,))
-            return message
-
-        def check_attachment((decrypted, _)):
-            msg = Parser().parsestr(decrypted)
-            for payload in msg.get_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(),
-                                    "Key attachment don't match")
-                    return
-            self.fail("No public key attachment found")
-
         d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
         d.addCallback(self._assert_encrypted)
-        d.addCallback(check_headers)
+        d.addCallback(self._check_headers, self.lines[:4])
         d.addCallback(lambda message: self._km.decrypt(
             message.get_payload(1).get_payload(), ADDRESS, openpgp.OpenPGPKey))
-        d.addCallback(check_attachment)
+        d.addCallback(lambda (decrypted, _):
+                      self._check_key_attachment(Parser().parsestr(decrypted)))
         return d
 
+    def test_attach_key_not_known(self):
+        address = "someunknownaddress@somewhere.com"
+        lines = self.lines
+        lines[1] = "To: <%s>" % (address,)
+        raw = '\r\n'.join(lines)
+        dest = User(address, 'gateway.leap.se', self.proto, ADDRESS_2)
+
+        d = self.outgoing_mail._maybe_encrypt_and_sign(raw, dest)
+        d.addCallback(lambda (message, _):
+                      self._check_headers(message, lines[:4]))
+        d.addCallback(self._check_key_attachment)
+        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