Add public key as attachment

3 files changed, 92 insertions, 6 deletions

diff --git a/mail/src/leap/mail/outgoing/service.py b/mail/src/leap/mail/outgoing/service.py
index 88b8895e..97771870 100644
--- a/mail/src/leap/mail/outgoing/service.py
+++ b/mail/src/leap/mail/outgoing/service.py
@@ -18,6 +18,8 @@ import re
 from StringIO import StringIO
 from email.parser import Parser
 from email.mime.application import MIMEApplication
+from email.mime.multipart import MIMEMultipart
+from email.mime.text import MIMEText
 
 from OpenSSL import SSL
 
@@ -250,10 +252,48 @@ class OutgoingMail:
                 % (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 = 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)
         return d
 
+    def _maybe_attach_key(self, origmsg, from_address, to_address):
+        filename = "%s-email-key.asc" % (from_address,)
+
+        def attach_if_address_hasnt_encrypted(to_key):
+            # if the sign_used flag is true that means that we got an encrypted
+            # email from this address, because we conly check signatures on
+            # encrypted emails. In this case we don't attach.
+            # XXX: this might not be true some time in the future
+            if to_key.sign_used:
+                return origmsg
+
+            d = self._keymanager.get_key(from_address, OpenPGPKey,
+                                         fetch_remote=False)
+            d.addCallback(attach_key)
+            return d
+
+        def attach_key(from_key):
+            msg = origmsg
+            if not origmsg.is_multipart():
+                msg = MIMEMultipart()
+                for h, v in origmsg.items():
+                    msg.add_header(h, v)
+                msg.attach(MIMEText(origmsg.get_payload()))
+
+            keymsg = MIMEApplication(from_key.key_data, _subtype='pgp-keys',
+                                     _encoder=lambda x: x)
+            keymsg.add_header('content-disposition', 'attachment',
+                              filename=filename)
+            msg.attach(keymsg)
+            return msg
+
+        d = self._keymanager.get_key(to_address, OpenPGPKey,
+                                     fetch_remote=False)
+        d.addCallback(attach_if_address_hasnt_encrypted)
+        d.addErrback(lambda _: origmsg)
+        return d
+
     def _encrypt_and_sign(self, origmsg, encrypt_address, sign_address):
         """
         Create an RFC 3156 compliang PGP encrypted and signed message using
diff --git a/mail/src/leap/mail/outgoing/tests/test_outgoing.py b/mail/src/leap/mail/outgoing/tests/test_outgoing.py
index d7423b69..0eb05c87 100644
--- a/mail/src/leap/mail/outgoing/tests/test_outgoing.py
+++ b/mail/src/leap/mail/outgoing/tests/test_outgoing.py
@@ -21,6 +21,7 @@ SMTP gateway tests.
 """
 
 import re
+from email.parser import Parser
 from datetime import datetime
 from twisted.internet.defer import fail
 from twisted.mail.smtp import User
@@ -33,10 +34,14 @@ from leap.mail.tests import (
     TestCaseWithKeyManager,
     ADDRESS,
     ADDRESS_2,
+    PUBLIC_KEY_2,
 )
 from leap.keymanager import openpgp, errors
 
 
+BEGIN_PUBLIC_KEY = "-----BEGIN PGP PUBLIC KEY BLOCK-----"
+
+
 class TestOutgoingMail(TestCaseWithKeyManager):
     EMAIL_DATA = ['HELO gateway.leap.se',
                   'MAIL FROM: <%s>' % ADDRESS_2,
@@ -71,7 +76,7 @@ class TestOutgoingMail(TestCaseWithKeyManager):
                 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)
+            self.dest = User(ADDRESS, 'gateway.leap.se', self.proto, ADDRESS_2)
 
         d = TestCaseWithKeyManager.setUp(self)
         d.addCallback(init_outgoing_and_proto)
@@ -88,7 +93,10 @@ class TestOutgoingMail(TestCaseWithKeyManager):
                 decrypted,
                 'Decrypted text differs from plaintext.')
 
-        d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
+        d = self._set_sign_used(ADDRESS)
+        d.addCallback(
+            lambda _:
+            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))
@@ -109,7 +117,10 @@ class TestOutgoingMail(TestCaseWithKeyManager):
             self.assertTrue(ADDRESS_2 in signkey.address,
                             "Verification failed")
 
-        d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
+        d = self._set_sign_used(ADDRESS)
+        d.addCallback(
+            lambda _:
+            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,
@@ -158,7 +169,7 @@ class TestOutgoingMail(TestCaseWithKeyManager):
 
             def assert_verify(key):
                 self.assertTrue(ADDRESS_2 in key.address,
-                                 'Signature could not be verified.')
+                                'Signature could not be verified.')
 
             d = self._km.verify(
                 signed_text, ADDRESS_2, openpgp.OpenPGPKey,
@@ -171,6 +182,42 @@ class TestOutgoingMail(TestCaseWithKeyManager):
         d.addCallback(verify)
         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(lambda message: self._km.decrypt(
+            message.get_payload(1).get_payload(), ADDRESS, openpgp.OpenPGPKey))
+        d.addCallback(check_attachment)
+        return d
+
+    def _set_sign_used(self, address):
+        def set_sign(key):
+            key.sign_used = True
+            return self._km.put_key(key, address)
+
+        d = self._km.get_key(address, openpgp.OpenPGPKey, fetch_remote=False)
+        d.addCallback(set_sign)
+        return d
+
     def _assert_encrypted(self, res):
         message, _ = res
         self.assertTrue('Content-Type' in message)
diff --git a/mail/src/leap/mail/smtp/gateway.py b/mail/src/leap/mail/smtp/gateway.py
index 9d78474b..954a7d0f 100644
--- a/mail/src/leap/mail/smtp/gateway.py
+++ b/mail/src/leap/mail/smtp/gateway.py
@@ -309,5 +309,4 @@ class EncryptedMessage(object):
         signal(proto.SMTP_CONNECTION_LOST, self._user.dest.addrstr)
         # unexpected loss of connection; don't save
 
-
         self._lines = []