Upgrade keys if not successfully used and strict high validation level

4 files changed, 127 insertions, 21 deletions

diff --git a/changes/feature-6211_succesfully_used b/changes/feature-6211_succesfully_used
new file mode 100644
index 00000000..74f0bba0
--- /dev/null
+++ b/changes/feature-6211_succesfully_used
@@ -0,0 +1 @@
+- Upgrade keys if not successfully used and strict high validation level (closes: #6211)
diff --git a/src/leap/keymanager/__init__.py b/src/leap/keymanager/__init__.py
index c4050fa8..fdbc206d 100644
--- a/src/leap/keymanager/__init__.py
+++ b/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/src/leap/keymanager/tests/test_validation.py b/src/leap/keymanager/tests/test_validation.py
index 83a02e00..a8b35ca3 100644
--- a/src/leap/keymanager/tests/test_validation.py
+++ b/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
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 AQ0EG+t93QEIAKqRq/2sBDW4g3FU+11LhixT+GosrfVvnitz3S9k2tBXok/wYpI1
 XeA+kTHiF0LaqoaciDRvkA9DvhDbSrNM1yeuYRyZiHlTmoPZ/Fkl60oA2cyLd1L5
 sXbuipY3TEiakugdSU4rzgi0hFycm6Go6yq2G6eC6UALvD9CTMdZHw40TadG9xpm
 4thYPuJ1kPH8/bkbTi9sLHoApYgL+7ssje8w4epr0qD4IGxeKwJPf/tbTRpnd8w3
 leldixHHKAutNt49p0pkXlORAHRpUmp+KMZhFvCvIPwe9o5mYtMR7sDRxjY61ZEQ
-KLyKoh5wsJsaPXBjdG7cf6G/cBcwvnQVUHcAEQEAAYkBJQQYAQIADwUCG+t93QIb
-DAUJAAFRgAAKCRBvFfAEoYhafOPgB/9z4YCyT/N0262HtegHykhsyykuqEeNb1LV
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-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)
+
+lQOYBBvrfd0BCADGNpspaNhsbhSjKioCWrE2MTTYC+Sdpes22RabdhQyOCWvlSbj
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+HEsoyd7WOsuse7+NkyUHgMXMVW7cz+nU7iO+ht2rkBtv+Z5LGlzgHTeFjKci
+=dZE8
+-----END PGP PRIVATE KEY BLOCK-----
+"""
 
 
 import unittest
diff --git a/src/leap/keymanager/validation.py b/src/leap/keymanager/validation.py
index 87de2af8..b3aff3e4 100644
--- a/src/leap/keymanager/validation.py
+++ b/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