Upgrade keys if not successfully used and strict high validation level

4 files changed, 127 insertions, 21 deletions

diff --git a/keymanager/changes/feature-6211_succesfully_used b/keymanager/changes/feature-6211_succesfully_used
new file mode 100644
index 00000000..74f0bba0
--- /dev/null
+++ b/keymanager/changes/feature-6211_succesfully_used
@@ -0,0 +1 @@
+- Upgrade keys if not successfully used and strict high validation level (closes: #6211)
diff --git a/keymanager/src/leap/keymanager/__init__.py b/keymanager/src/leap/keymanager/__init__.py
index c4050fa8..fdbc206d 100644
--- a/keymanager/src/leap/keymanager/__init__.py
+++ b/keymanager/src/leap/keymanager/__init__.py
@@ -476,9 +476,13 @@ class KeyManager(object):
 
         def encrypt(keys):
             pubkey, signkey = keys
-            return self._wrapper_map[ktype].encrypt(
+            encrypted = self._wrapper_map[ktype].encrypt(
                 data, pubkey, passphrase, sign=signkey,
                 cipher_algo=cipher_algo)
+            pubkey.encr_used = True
+            d = self._wrapper_map[ktype].put_key(pubkey, address)
+            d.addCallback(lambda _: encrypted)
+            return d
 
         dpub = self.get_key(address, ktype, private=False,
                             fetch_remote=fetch_remote)
@@ -529,7 +533,10 @@ class KeyManager(object):
             if pubkey is None:
                 signature = KeyNotFound(verify)
             elif signed:
-                signature = pubkey
+                pubkey.sign_used = True
+                d = self._wrapper_map[ktype].put_key(pubkey, address)
+                d.addCallback(lambda _: (decrypted, pubkey))
+                return d
             else:
                 signature = InvalidSignature(
                     'Failed to verify signature with key %s' %
@@ -621,7 +628,10 @@ class KeyManager(object):
             signed = self._wrapper_map[ktype].verify(
                 data, pubkey, detached_sig=detached_sig)
             if signed:
-                return pubkey
+                pubkey.sign_used = True
+                d = self._wrapper_map[ktype].put_key(pubkey, address)
+                d.addCallback(lambda _: pubkey)
+                return d
             else:
                 raise InvalidSignature(
                     'Failed to verify signature with key %s' %
@@ -718,9 +728,12 @@ class KeyManager(object):
         :raise UnsupportedKeyTypeError: if invalid key type
         """
         self._assert_supported_key_type(ktype)
-        pubkey, _ = self._wrapper_map[ktype].parse_ascii_key(key)
+        pubkey, privkey = self._wrapper_map[ktype].parse_ascii_key(key)
         pubkey.validation = validation
-        return self.put_key(pubkey, address)
+        d = self.put_key(pubkey, address)
+        if privkey is not None:
+            d.addCallback(lambda _: self.put_key(privkey, address))
+        return d
 
     def fetch_key(self, address, uri, ktype,
                   validation=ValidationLevel.Weak_Chain):
diff --git a/keymanager/src/leap/keymanager/tests/test_validation.py b/keymanager/src/leap/keymanager/tests/test_validation.py
index 83a02e00..a8b35ca3 100644
--- a/keymanager/src/leap/keymanager/tests/test_validation.py
+++ b/keymanager/src/leap/keymanager/tests/test_validation.py
@@ -89,6 +89,34 @@ class ValidationLevelTestCase(KeyManagerWithSoledadTestCase):
         key = yield km.get_key(ADDRESS, OpenPGPKey, fetch_remote=False)
         self.assertEqual(key.expiry_date, EXPIRED_KEY_NEW_EXPIRY_DATE)
 
+    @inlineCallbacks
+    def test_not_used(self):
+        km = self._key_manager()
+        yield km.put_raw_key(UNEXPIRED_KEY, OpenPGPKey, ADDRESS,
+                             validation=ValidationLevel.Provider_Trust)
+        yield km.put_raw_key(UNRELATED_KEY, OpenPGPKey, ADDRESS,
+                             validation=ValidationLevel.Provider_Endorsement)
+        key = yield km.get_key(ADDRESS, OpenPGPKey, fetch_remote=False)
+        self.assertEqual(key.fingerprint, UNRELATED_FINGERPRINT)
+
+    @inlineCallbacks
+    def test_used(self):
+        TEXT = "some text"
+
+        km = self._key_manager()
+        yield km.put_raw_key(UNEXPIRED_KEY, OpenPGPKey, ADDRESS)
+        yield km.encrypt(TEXT, ADDRESS, OpenPGPKey)
+
+        km2 = self._key_manager()
+        yield km2.put_raw_key(UNEXPIRED_PRIVATE, OpenPGPKey, ADDRESS)
+        signature = yield km2.sign(TEXT, ADDRESS, OpenPGPKey)
+
+        yield km.verify(TEXT, ADDRESS, OpenPGPKey, detached_sig=signature)
+        d = km.put_raw_key(
+            UNRELATED_KEY, OpenPGPKey, ADDRESS,
+            validation=ValidationLevel.Provider_Endorsement)
+        yield self.assertFailure(d, KeyNotValidUpgrade)
+
 
 # Key material for testing
 
@@ -162,7 +190,7 @@ Osuse7+NkyUHgMXMVW7cz+nU7iO+ht2rkBtv+Z5LGlzgHTeFjKci
 -----END PGP PUBLIC KEY BLOCK-----
 """
 # updated expiration date
-EXPIRED_KEY_NEW_EXPIRY_DATE = datetime.fromtimestamp(2045319180)
+EXPIRED_KEY_NEW_EXPIRY_DATE = datetime.fromtimestamp(2049717872)
 EXPIRED_KEY_UPDATED = """
 -----BEGIN PGP PUBLIC KEY BLOCK-----
 Version: GnuPG v1.4.12 (GNU/Linux)
@@ -174,27 +202,87 @@ acDh9vNtPxDCg5RdI0bfdIEBGgHTfsda3kWGvo1wH5SgrTRq0+EcTI7aJgkMmM/A
 IhnpACE52NvGdG9eB3x7xyQFsQqK8F0XvEev2UJH4SR7vb+Z7FNTJKCy6likYbSV
 wGGFuowFSESnzXuUI6PcjyuO6FUbMgeM5euFABEBAAG0HExlYXAgVGVzdCBLZXkg
 PGxlYXBAbGVhcC5zZT6JAT4EEwECACgCGwMGCwkIBwMCBhUIAgkKCwQWAgMBAh4B
-AheABQJUURIXBQld/ZovAAoJEG8V8AShiFp8xUcIALcAHZbaxvyhHRGOrwDddbH0
-fFDK0AqKTsIT7y4D/HLFCP5zG3Ck7qGPZdkHXZfzq8rIb+zUjW3oJIVI1IucHxG2
-T5kppa8RFCBAFlRWYf6R3isX3YL0d3QSragjoxRNPcHNU8ALHcvfSonFHBoi4fH4
-4rvgksAiT68SsdPaoXDlabx5T15evu/7T5e/DGMQVPMxiaSuSQhbOKuMk2wcFdmL
-tBYHLZPa54hHPNhEDyxLgtKKph0gObk9ojKfH9kPvLveIcpS5CqTJfN/kqBz7CJW
-wEeAi2iG3H1OEB25aCUdTxXSRNlGqEgcWPaWxtc1RzlARu7LB64OUZuRy4puiAG5
+AheABQJUlDCSBQleQLiTAAoJEG8V8AShiFp8t3QH/1eqkVIScXmqaCVeno3VSKiH
+HqnxiHcEgtpNRfUlP6tLD4H6QPEpvoUI9S/8HSYi3nbDGXEX8ycKlnwxjdIqWSOW
+xj91/7uQAo+dP9QaVJ6xgaAiqzN1x3JzX3Js1wTodmNV0TfmGjxwnC5up/xK7/pd
+KuDP3woDsRlwy8Lgj67mkn49xfAFHo6hI6SD36UBDAC/ELq6kZaba4Kk0fEVHCEz
+HX0B09ZIY9fmf305cEB3dNh6SMQgKtH0wKozaqI2UM2B+cs3z08bC+YuUUh7UJTH
+yr+hI7vF4/WEeJB3fuhP3xsumLhV8P47DaJ7oivmtsDEbAJFKqvigEqNES73Xpy5
 AQ0EG+t93QEIAKqRq/2sBDW4g3FU+11LhixT+GosrfVvnitz3S9k2tBXok/wYpI1
 XeA+kTHiF0LaqoaciDRvkA9DvhDbSrNM1yeuYRyZiHlTmoPZ/Fkl60oA2cyLd1L5
 sXbuipY3TEiakugdSU4rzgi0hFycm6Go6yq2G6eC6UALvD9CTMdZHw40TadG9xpm
 4thYPuJ1kPH8/bkbTi9sLHoApYgL+7ssje8w4epr0qD4IGxeKwJPf/tbTRpnd8w3
 leldixHHKAutNt49p0pkXlORAHRpUmp+KMZhFvCvIPwe9o5mYtMR7sDRxjY61ZEQ
-KLyKoh5wsJsaPXBjdG7cf6G/cBcwvnQVUHcAEQEAAYkBJQQYAQIADwUCG+t93QIb
-DAUJAAFRgAAKCRBvFfAEoYhafOPgB/9z4YCyT/N0262HtegHykhsyykuqEeNb1LV
-D9INcP+RbCX/0IjFgP4DTMPP7qqF1OBwR276maALT321Gqxc5HN5YrwxGdmoyBLm
-unaQJJlD+7B1C+jnO6r4m44obvJ/NMERxVyzkXap3J2VgRIO1wNLI9I0sH6Kj5/j
-Mgy06OwXDcqIc+jB4sIJ3Tnm8LZ3phJzNEm9mI8Ak0oJ7IEcMndR6DzmRt1rJQcq
-K/D7hOG02zvyRhxF27U1qR1MxeU/gNnOx8q4dnVyWB+EiV1sFl4iTOyYHEsoyd7W
-Osuse7+NkyUHgMXMVW7cz+nU7iO+ht2rkBtv+Z5LGlzgHTeFjKci
-=79Ll
+KLyKoh5wsJsaPXBjdG7cf6G/cBcwvnQVUHcAEQEAAYkBJQQYAQIADwIbDAUCVJQw
+3QUJXkC4/QAKCRBvFfAEoYhafEtiB/9hMfSFNMxtlIJDJArG4JwR7sBOatYUT858
+qZnTgGETZN8wXpeEpXWKdDdmCX9aeE9jsDNgSQ5WWpqU21bGMXh1IGjAzmqTqq3/
+ik1vALuaVfr6OqjTzrJVQujT61CGed26xpP3Zh8hLKyKa+dXnX/VpgZS42wZLPx2
+wcODfANmTfE2AhMap/RyDy21q4nau+z2hMEOKdtF8dpP+pEvzoN5ZexYP1hfT+Av
+oFPyVB5YtEMfxTEshDKRPjbdgNmw4faKXd5Cbelo4YxxpO16FHb6gzIdjOX15vQ+
+KwcVXzg9xk4D3cr1mnTCops/iv6TXvcw4Wbo70rrKXwkjl8LKjOP
+=sHoe
 -----END PGP PUBLIC KEY BLOCK-----
 """
+UNEXPIRED_KEY = EXPIRED_KEY_UPDATED
+UNEXPIRED_PRIVATE = """
+-----BEGIN PGP PRIVATE KEY BLOCK-----
+Version: GnuPG v1.4.12 (GNU/Linux)
+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dZE8
+-----END PGP PRIVATE KEY BLOCK-----
+"""
 
 
 import unittest
diff --git a/keymanager/src/leap/keymanager/validation.py b/keymanager/src/leap/keymanager/validation.py
index 87de2af8..b3aff3e4 100644
--- a/keymanager/src/leap/keymanager/validation.py
+++ b/keymanager/src/leap/keymanager/validation.py
@@ -60,7 +60,6 @@ def can_upgrade(new_key, old_key):
     :type old_key: EncryptionKey
     :rtype: bool
     """
-    # XXX not succesfully used and strict high validation level (#6211)
     # XXX implement key signature checking (#6120)
 
     # First contact
@@ -86,4 +85,9 @@ def can_upgrade(new_key, old_key):
             new_key.validation > old_key.validation):
         return True
 
+    # Not successfully used and strict high validation level
+    if (not (old_key.sign_used and old_key.encr_used) and
+            new_key.validation > old_key.validation):
+        return True
+
     return False