feat: hash support for user auth token middleware

src/sentry/api/authentication.py

@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import hashlib
 from collections.abc import Callable, Iterable
 from typing import Any, ClassVar
 
@@ -298,6 +299,55 @@ def authenticate(self, request: Request):
 class UserAuthTokenAuthentication(StandardAuthentication):
     token_name = b"bearer"
 
+    def _find_or_update_token_by_hash(self, token_str: str) -> ApiToken | ApiTokenReplica:
+        """
+        Find token by hash or update token's hash value if only found via plaintext.
+
+        1. Hash provided plaintext token.
+        2. Perform lookup based on hashed value.
+        3. If found, return the token.
+        4. If not found, search for the token based on its plaintext value.
+        5. If found, update the token's hashed value and return the token.
+        6. If not found via hash or plaintext value, raise AuthenticationFailed
+
+        Returns `ApiTokenReplica` if running in REGION silo or
+        `ApiToken` if running in CONTROL silo.
+        """
+
+        hashed_token = hashlib.sha256(token_str.encode()).hexdigest()
+
+        if SiloMode.get_current_mode() == SiloMode.REGION:
+            try:
+                # Try to find the token by its hashed value first
+                return ApiTokenReplica.objects.get(hashed_token=hashed_token)
+            except ApiTokenReplica.DoesNotExist:
+                try:
+                    # If we can't find it by hash, use the plaintext string
+                    return ApiTokenReplica.objects.get(token=token_str)
+                except ApiTokenReplica.DoesNotExist:
+                    # If the token does not exist by plaintext either, it is not a valid token
+                    raise AuthenticationFailed("Invalid token")
+        else:
+            try:
+                # Try to find the token by its hashed value first
+                return ApiToken.objects.select_related("user", "application").get(
+                    hashed_token=hashed_token
+                )
+            except ApiToken.DoesNotExist:
+                try:
+                    # If we can't find it by hash, use the plaintext string
+                    api_token = ApiToken.objects.select_related("user", "application").get(
+                        token=token_str
+                    )
+                except ApiToken.DoesNotExist:
+                    # If the token does not exist by plaintext either, it is not a valid token
+                    raise AuthenticationFailed("Invalid token")
+                else:
+                    # Update it with the hashed value if found by plaintext
+                    api_token.hashed_token = hashed_token
+                    api_token.save(update_fields=["hashed_token"])
+                    return api_token
+
     def accepts_auth(self, auth: list[bytes]) -> bool:
         if not super().accepts_auth(auth):
             return False
@@ -320,26 +370,16 @@ def authenticate_token(self, request: Request, token_str: str) -> tuple[Any, Any
         application_is_inactive = False
 
         if not token:
-            if SiloMode.get_current_mode() == SiloMode.REGION:
-                try:
-                    atr = token = ApiTokenReplica.objects.get(token=token_str)
-                except ApiTokenReplica.DoesNotExist:
-                    raise AuthenticationFailed("Invalid token")
-                user = user_service.get_user(user_id=atr.user_id)
-                application_is_inactive = not atr.application_is_active
-            else:
-                try:
-                    at = token = (
-                        ApiToken.objects.filter(token=token_str)
-                        .select_related("user", "application")
-                        .get()
-                    )
-                except ApiToken.DoesNotExist:
-                    raise AuthenticationFailed("Invalid token")
-                user = at.user
+            token = self._find_or_update_token_by_hash(token_str)
+            if isinstance(token, ApiTokenReplica):  # we're running as a REGION silo
+                user = user_service.get_user(user_id=token.user_id)
+                application_is_inactive = not token.application_is_active
+            else:  # the token returned is an ApiToken from the CONTROL silo
+                user = token.user
                 application_is_inactive = (
-                    at.application is not None and not at.application.is_active
+                    token.application is not None and not token.application.is_active
                 )
+
         elif isinstance(token, SystemToken):
             user = token.user
 
@@ -389,9 +429,9 @@ def authenticate_token(self, request: Request, token_str: str) -> tuple[Any, Any
                 raise AuthenticationFailed("Invalid org token")
         else:
             try:
-                token = OrgAuthToken.objects.filter(
+                token = OrgAuthToken.objects.get(
                     token_hashed=token_hashed, date_deactivated__isnull=True
-                ).get()
+                )
             except OrgAuthToken.DoesNotExist:
                 raise AuthenticationFailed("Invalid org token")
 

src/sentry/options/defaults.py

@@ -271,6 +271,12 @@
     type=Bool,
     flags=FLAG_ALLOW_EMPTY | FLAG_PRIORITIZE_DISK | FLAG_AUTOMATOR_MODIFIABLE,
 )
+register(
+    "apitoken.save-hash-on-create",
+    default=True,
+    type=Bool,
+    flags=FLAG_ALLOW_EMPTY | FLAG_PRIORITIZE_DISK | FLAG_AUTOMATOR_MODIFIABLE,
+)
 
 register(
     "api.rate-limit.org-create",

src/sentry/services/hybrid_cloud/auth/model.py

@@ -34,6 +34,7 @@ class RpcApiToken(RpcModel):
     application_id: int | None = None
     application_is_active: bool = False
     token: str = ""
+    hashed_token: str | None = None
     expires_at: datetime.datetime | None = None
     allowed_origins: list[str] = Field(default_factory=list)
     scope_list: list[str] = Field(default_factory=list)

src/sentry/services/hybrid_cloud/auth/serial.py

@@ -87,6 +87,7 @@ def serialize_api_token(at: ApiToken) -> RpcApiToken:
         organization_id=at.organization_id,
         application_is_active=at.application_id is None or at.application.is_active,
         token=at.token,
+        hashed_token=at.hashed_token,
         expires_at=at.expires_at,
         allowed_origins=list(at.get_allowed_origins()),
         scope_list=at.get_scopes(),

src/sentry/services/hybrid_cloud/replica/impl.py

@@ -160,6 +160,7 @@ def upsert_replicated_api_token(self, *, api_token: RpcApiToken, region_name: st
             organization=organization,
             application_is_active=api_token.application_is_active,
             token=api_token.token,
+            hashed_token=api_token.hashed_token,
             expires_at=api_token.expires_at,
             apitoken_id=api_token.id,
             scope_list=api_token.scope_list,

tests/sentry/api/test_authentication.py

@@ -1,3 +1,4 @@
+import hashlib
 import uuid
 from datetime import UTC, datetime
 
@@ -30,8 +31,11 @@
 )
 from sentry.silo import SiloMode
 from sentry.testutils.cases import TestCase
+from sentry.testutils.helpers import override_options
+from sentry.testutils.outbox import outbox_runner
 from sentry.testutils.pytest.fixtures import django_db_all
 from sentry.testutils.silo import assume_test_silo_mode, control_silo_test, no_silo_test
+from sentry.types.token import AuthTokenType
 from sentry.utils.security.orgauthtoken_token import hash_token
 
 
@@ -202,6 +206,71 @@ def test_no_match(self):
         with pytest.raises(AuthenticationFailed):
             self.auth.authenticate(request)
 
+    @override_options({"apitoken.save-hash-on-create": False})
+    def test_token_hashed_with_option_off(self):
+        # see https://github.com/getsentry/sentry/pull/65941
+        # the UserAuthTokenAuthentication middleware was updated to hash tokens as
+        # they were used, this test verifies the hash
+        api_token = ApiToken.objects.create(user=self.user, token_type=AuthTokenType.USER)
+        expected_hash = hashlib.sha256(api_token.token.encode()).hexdigest()
+
+        # we haven't authenticated to the API endpoint yet, so this value should be empty
+        assert api_token.hashed_token is None
+
+        request = HttpRequest()
+        request.META["HTTP_AUTHORIZATION"] = f"Bearer {api_token.token}"
+
+        # trigger the authentication middleware, and thus the hashing
+        result = self.auth.authenticate(request)
+        assert result is not None
+
+        # check for the expected hash value
+        api_token.refresh_from_db()
+        assert api_token.hashed_token == expected_hash
+
+
+@no_silo_test
+class TestTokenAuthenticationReplication(TestCase):
+    def setUp(self):
+        super().setUp()
+
+        self.auth = UserAuthTokenAuthentication()
+
+    @override_options({"apitoken.save-hash-on-create": False})
+    def test_hash_is_replicated(self):
+        api_token = ApiToken.objects.create(user=self.user, token_type=AuthTokenType.USER)
+        expected_hash = hashlib.sha256(api_token.token.encode()).hexdigest()
+
+        # we haven't authenticated to the API endpoint yet, so this value should be empty
+        assert api_token.hashed_token is None
+
+        request = HttpRequest()
+        request.META["HTTP_AUTHORIZATION"] = f"Bearer {api_token.token}"
+
+        with assume_test_silo_mode(SiloMode.REGION):
+            with outbox_runner():
+                # make sure the token was replicated
+                api_token_replica = ApiTokenReplica.objects.get(apitoken_id=api_token.id)
+                assert api_token.token == api_token_replica.token
+                assert (
+                    api_token_replica.hashed_token is None
+                )  # we don't expect to have a hashed value yet
+
+                # trigger the authentication middleware, and thus the hashing backfill
+                result = self.auth.authenticate(request)
+                assert result is not None
+
+                # check for the expected hash value
+                api_token.refresh_from_db()
+                assert api_token.hashed_token == expected_hash
+
+                # ApiTokenReplica should also be updated
+                api_token_replica.refresh_from_db()
+                assert api_token_replica.hashed_token == expected_hash
+
+                # just for good measure
+                assert api_token.hashed_token == api_token_replica.hashed_token
+
 
 @django_db_all
 @pytest.mark.parametrize("internal", [True, False])