def test_message_sign(self):
"""
Test if message is signed with sender key.
"""
# mock the key fetching
self.km._fetch_keys_from_server = Mock(
return_value=fail(errors.KeyNotFound()))
recipient = User('*****@*****.**',
'gateway.leap.se', self.proto, ADDRESS)
self.outgoing_mail = OutgoingMail(
self.fromAddr, self.km, self.opts.cert, self.opts.key,
self.opts.hostname, self.opts.port)
def check_signed(res):
message, _ = res
self.assertTrue('Content-Type' in message)
self.assertEqual('multipart/signed', message.get_content_type())
self.assertEqual('application/pgp-signature',
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,
body)
# assert content of signature
self.assertTrue(
message.get_payload(1).get_payload().startswith(
'-----BEGIN PGP SIGNATURE-----\n'),
'Message does not start with signature header.')
self.assertTrue(
message.get_payload(1).get_payload().endswith(
'-----END PGP SIGNATURE-----\n'),
'Message does not end with signature footer.')
return message
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',
fp.getvalue())
def assert_verify(key):
self.assertTrue(ADDRESS_2 in key.address,
'Signature could not be verified.')
d = self.km.verify(
signed_text, ADDRESS_2,
detached_sig=message.get_payload(1).get_payload())
d.addCallback(assert_verify)
return d
d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, recipient)
d.addCallback(check_signed)
d.addCallback(verify)
return d
def test_send_error_raises_exception_if_there_is_no_bouncer(self):
bouncer = None
outgoing_mail = OutgoingMail(self.from_address, self.keymanager,
bouncer)
failure = Failure(exc_value=Exception('smtp error'))
origmsg = 'message'
with self.assertRaises(Exception):
outgoing_mail.sendError(failure, origmsg)
def test_send_error_bounces_if_bouncer_is_provided(self):
bouncer = MagicMock()
outgoing_mail = OutgoingMail(self.from_address, self.keymanager,
bouncer)
failure = Failure(exc_value=Exception())
origmsg = 'message'
outgoing_mail.sendError(failure, origmsg)
bouncer.bounce_message.assert_called()
def init_outgoing_and_proto(_):
self.outgoing_mail = OutgoingMail(
self.fromAddr, self.km, opts.cert,
opts.key, opts.hostname, opts.port)
user = TEST_USER
# TODO -- this shouldn't need SMTP to be tested!? or does it?
self.proto = getSMTPFactory(
{user: None}, {user: self.km}, {user: None})
self.dest = User(ADDRESS, 'gateway.leap.se', self.proto, ADDRESS_2)
def _create_outgoing_service(self, bouncer, userid, keymanager, soledad):
outgoing = OutgoingMail(userid, keymanager, bouncer)
username, provider = userid.split('@')
key = _get_smtp_client_cert_path(self._basedir, provider, username)
prov = _get_provider_for_service('smtp', self._basedir, provider)
hostname = prov.hostname
port = prov.port
if not os.path.isfile(key):
raise errors.ConfigurationError(
'No valid SMTP certificate could be found for %s!' % userid)
smtp_sender = SMTPSender(userid, key, hostname, port)
outgoing.add_sender(smtp_sender)
self._outgoing_sessions[userid] = outgoing
def test_missing_key_rejects_address(self):
"""
Test if server rejects to send unencrypted when 'encrypted_only' is
True.
"""
# remove key from key manager
pubkey = yield self.km.get_key(ADDRESS)
pgp = openpgp.OpenPGPScheme(self._soledad,
gpgbinary=self.gpg_binary_path)
yield pgp.delete_key(pubkey)
# mock the key fetching
self.km._nicknym.fetch_key_with_address = Mock(
return_value=fail(errors.KeyNotFound()))
user = TEST_USER
proto = getSMTPFactory({user: OutgoingMail(user, self.km)},
{user: None},
encrypted_only=True)
transport = proto_helpers.StringTransport()
proto.makeConnection(transport)
yield self.getReply(self.EMAIL_DATA[0] + '\r\n', proto, transport)
yield self.getReply(self.EMAIL_DATA[1] + '\r\n', proto, transport)
reply = yield self.getReply(self.EMAIL_DATA[2] + '\r\n', proto,
transport)
# ensure the address was rejected
self.assertEqual(
'550 Cannot receive for specified address\r\n', reply,
'Address should have been rejected with appropriate message.')
proto.setTimeout(None)
def test_missing_key_accepts_address(self):
"""
Test if server accepts to send unencrypted when 'encrypted_only' is
False.
"""
# remove key from key manager
pubkey = yield self.km.get_key(ADDRESS)
pgp = openpgp.OpenPGPScheme(self._soledad,
gpgbinary=self.gpg_binary_path)
yield pgp.delete_key(pubkey)
# mock the key fetching
self.km._fetch_keys_from_server_and_store_local = Mock(
return_value=fail(errors.KeyNotFound()))
user = TEST_USER
proto = getSMTPFactory({user: OutgoingMail(user, self.km)},
{user: None})
transport = proto_helpers.StringTransport()
proto.makeConnection(transport)
yield self.getReply(self.EMAIL_DATA[0] + '\r\n', proto, transport)
yield self.getReply(self.EMAIL_DATA[1] + '\r\n', proto, transport)
reply = yield self.getReply(self.EMAIL_DATA[2] + '\r\n', proto,
transport)
# ensure the address was accepted
self.assertEqual(
'250 Recipient address accepted\r\n', reply,
'Address should have been accepted with appropriate message.')
proto.setTimeout(None)
def test_gateway_accepts_valid_email(self):
"""
Test if SMTP server responds correctly for valid interaction.
"""
SMTP_ANSWERS = [
'220 ' + IP_OR_HOST_REGEX + ' NO UCE NO UBE NO RELAY PROBES',
'250 ' + IP_OR_HOST_REGEX + ' Hello ' + IP_OR_HOST_REGEX +
', nice to meet you', '250 Sender address accepted',
'250 Recipient address accepted', '354 Continue'
]
user = TEST_USER
proto = getSMTPFactory({user: OutgoingMail(user, self.km)},
{user: None})
transport = proto_helpers.StringTransport()
proto.makeConnection(transport)
reply = ""
for i, line in enumerate(self.EMAIL_DATA):
reply += yield self.getReply(line + '\r\n', proto, transport)
self.assertMatch(reply, '\r\n'.join(SMTP_ANSWERS),
'Did not get expected answer from gateway.')
proto.setTimeout(None)
class TestOutgoingMail(KeyManagerWithSoledadTestCase):
EMAIL_DATA = ['HELO gateway.leap.se',
'MAIL FROM: <%s>' % ADDRESS_2,
'RCPT TO: <%s>' % ADDRESS,
'DATA',
'From: User <%s>' % ADDRESS_2,
'To: Leap <%s>' % ADDRESS,
'Date: ' + datetime.now().strftime('%c'),
'Subject: test message',
'',
'This is a secret message.',
'Yours,',
'A.',
'',
'.',
'QUIT']
def setUp(self):
self.lines = [line for line in self.EMAIL_DATA[4:12]]
self.lines.append('') # add a trailing newline
self.raw = '\r\n'.join(self.lines)
self.expected_body = '\r\n'.join(self.EMAIL_DATA[9:12]) + "\r\n"
self.fromAddr = ADDRESS_2
class opts:
cert = u'/tmp/cert'
key = u'/tmp/cert'
hostname = 'remote'
port = 666
self.opts = opts
def init_outgoing_and_proto(_):
self.outgoing_mail = OutgoingMail(
self.fromAddr, self.km, opts.cert,
opts.key, opts.hostname, opts.port)
user = TEST_USER
# TODO -- this shouldn't need SMTP to be tested!? or does it?
self.proto = getSMTPFactory(
{user: None}, {user: self.km}, {user: None})
self.dest = User(ADDRESS, 'gateway.leap.se', self.proto, ADDRESS_2)
d = KeyManagerWithSoledadTestCase.setUp(self)
d.addCallback(init_outgoing_and_proto)
return d
def test_message_encrypt(self):
"""
Test if message gets encrypted to destination email.
"""
def check_decryption(res):
decrypted, _ = res
self.assertEqual(
'\n' + self.expected_body,
decrypted,
'Decrypted text differs from plaintext.')
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))
d.addCallback(check_decryption)
return d
def test_message_encrypt_sign(self):
"""
Test if message gets encrypted to destination email and signed with
sender key.
'"""
def check_decryption_and_verify(res):
decrypted, signkey = res
self.assertEqual(
'\n' + self.expected_body,
decrypted,
'Decrypted text differs from plaintext.')
self.assertTrue(ADDRESS_2 in signkey.address,
"Verification failed")
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, verify=ADDRESS_2))
d.addCallback(check_decryption_and_verify)
return d
def test_message_sign(self):
"""
Test if message is signed with sender key.
"""
# mock the key fetching
self.km._fetch_keys_from_server = Mock(
return_value=fail(errors.KeyNotFound()))
recipient = User('*****@*****.**',
'gateway.leap.se', self.proto, ADDRESS)
self.outgoing_mail = OutgoingMail(
self.fromAddr, self.km, self.opts.cert, self.opts.key,
self.opts.hostname, self.opts.port)
def check_signed(res):
message, _ = res
self.assertTrue('Content-Type' in message)
self.assertEqual('multipart/signed', message.get_content_type())
self.assertEqual('application/pgp-signature',
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,
body)
# assert content of signature
self.assertTrue(
message.get_payload(1).get_payload().startswith(
'-----BEGIN PGP SIGNATURE-----\n'),
'Message does not start with signature header.')
self.assertTrue(
message.get_payload(1).get_payload().endswith(
'-----END PGP SIGNATURE-----\n'),
'Message does not end with signature footer.')
return message
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',
fp.getvalue())
def assert_verify(key):
self.assertTrue(ADDRESS_2 in key.address,
'Signature could not be verified.')
d = self.km.verify(
signed_text, ADDRESS_2,
detached_sig=message.get_payload(1).get_payload())
d.addCallback(assert_verify)
return d
d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, recipient)
d.addCallback(check_signed)
d.addCallback(verify)
return d
def test_attach_key(self):
d = self.outgoing_mail._maybe_encrypt_and_sign(self.raw, self.dest)
d.addCallback(self._assert_encrypted)
d.addCallback(self._check_headers, self.lines[:4])
d.addCallback(lambda message: self.km.decrypt(
message.get_payload(1).get_payload(), ADDRESS))
d.addCallback(lambda (decrypted, _):
self._check_key_attachment(Parser().parsestr(decrypted)))
return d
def test_attach_key_not_known(self):
unknown_address = "*****@*****.**"
lines = deepcopy(self.lines)
lines[1] = "To: <%s>" % (unknown_address,)
raw = '\r\n'.join(lines)
dest = User(unknown_address, 'gateway.leap.se', self.proto, ADDRESS_2)
d = self.outgoing_mail._maybe_encrypt_and_sign(
raw, dest, fetch_remote=False)
d.addCallback(lambda (message, _):
self._check_headers(message, lines[:4]))
d.addCallback(self._check_key_attachment)
d.addErrback(log.err)
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
return self.km.put_key(key)
d = self.km.get_key(address, fetch_remote=False)
d.addCallback(set_sign)
return d
def _assert_encrypted(self, res):
message, _ = res
self.assertTrue('Content-Type' in message)
self.assertEqual('multipart/encrypted', message.get_content_type())
self.assertEqual('application/pgp-encrypted',
message.get_param('protocol'))
self.assertEqual(2, len(message.get_payload()))
self.assertEqual('application/pgp-encrypted',
message.get_payload(0).get_content_type())
self.assertEqual('application/octet-stream',
message.get_payload(1).get_content_type())
return message
def _create_outgoing_mail(self):
return OutgoingMail(str(self._smtp_config.account_email),
self._keymanager, self._smtp_config.cert_path,
self._smtp_config.cert_path,
str(self._smtp_config.remote_smtp_host),
int(self._smtp_config.remote_smtp_port))