diff --git a/litellm/proxy/mcp_server/discoverable_endpoints.py b/litellm/proxy/mcp_server/discoverable_endpoints.py
index f36609aa8b3..36a312d7c1f 100644
--- a/litellm/proxy/mcp_server/discoverable_endpoints.py
+++ b/litellm/proxy/mcp_server/discoverable_endpoints.py
@@ -110,6 +110,7 @@ from litellm.proxy.mcp_server.oauth_identity_binding import (
 from litellm.proxy.mcp_server.oauth_utils import (
     CIMD_METADATA_PATH,
     TOKEN_NO_CACHE_HEADERS,
+    asks_for_wildcard,
     build_upstream_authorize_url,
     build_upstream_oauth2_token_request,
     configured_proxy_base_url,
@@ -1066,7 +1067,10 @@ async def _managed_authorization_scope(
         if scope_user_id and prisma_client is not None
         else None
     )
-    merged_scope: Final = union_scopes(" ".join(prior_grant.get("scopes") or ()) if prior_grant else None, scope)
+    kept_scope: Final = (
+        None if prior_grant is None or asks_for_wildcard(scope) else " ".join(prior_grant.get("scopes") or ())
+    )
+    merged_scope: Final = union_scopes(kept_scope, scope)
     selected_scope: Final = (
         get_client_metadata_scopes(
             merged_scope,
diff --git a/litellm/proxy/mcp_server/oauth_utils.py b/litellm/proxy/mcp_server/oauth_utils.py
index 3171c476ede..c4fbaa7b087 100644
--- a/litellm/proxy/mcp_server/oauth_utils.py
+++ b/litellm/proxy/mcp_server/oauth_utils.py
@@ -132,18 +132,27 @@ def build_upstream_authorize_url(authorization_url: str, params: Mapping[str, st
     return urlunparse(parsed._replace(query=urlencode(merged)))
 
 
+MCP_WILDCARD_SCOPE: Final = "mcp_all"
+
+
+def asks_for_wildcard(scope: str | None) -> bool:
+    return MCP_WILDCARD_SCOPE in (scope or "").split()
+
+
 def grant_covers_scopes(
     granted: tuple[str, ...], requested: tuple[str, ...], server_scopes: Callable[[], frozenset[str]]
 ) -> bool:
-    """Whether a stored grant holds every requested scope. A grant stored as one comma-joined token, the form
-    Slack and GitHub reply with, counts as its parts only when every part is a requested or server scope."""
-    if all(scope in granted for scope in requested):
+    """Whether a stored grant holds every requested scope. A non-empty grant holds the wildcard scope, which a
+    provider grants as granular scopes in its place. A grant stored as one comma-joined token, the form Slack and
+    GitHub reply with, counts as its parts only when every part is a requested or server scope."""
+    held: Final = frozenset((*granted, MCP_WILDCARD_SCOPE)) if granted else frozenset[str]()
+    if all(scope in held for scope in requested):
         return True
     if len(granted) != 1 or "," not in granted[0]:
         return False
     parts: Final = frozenset(granted[0].split(","))
     known: Final = frozenset(requested) | server_scopes()
-    return parts <= known and all(scope in granted or scope in parts for scope in requested)
+    return parts <= known and all(scope in held or scope in parts for scope in requested)
 
 
 _PUBLISHED_SCOPES: Final = TypeAdapter[tuple[str, ...] | None](tuple[str, ...] | None)
diff --git a/tests/unit/proxy/mcp_server/test_discoverable_endpoints.py b/tests/unit/proxy/mcp_server/test_discoverable_endpoints.py
index 64413c4a74a..b42f558689c 100644
--- a/tests/unit/proxy/mcp_server/test_discoverable_endpoints.py
+++ b/tests/unit/proxy/mcp_server/test_discoverable_endpoints.py
@@ -14999,11 +14999,23 @@ async def test_saved_refresh_metadata_is_bound_to_the_callers_stored_grant(
 
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
-    "prior_scopes, expected", [(["tools.read"], "tools.read tools.write"), (None, "tools.write"), ([], "tools.write")]
+    "prior_scopes, scope, expected",
+    [
+        (["tools.read"], "tools.write", "tools.read tools.write"),
+        (None, "tools.write", "tools.write"),
+        ([], "tools.write", "tools.write"),
+        (["logs_read_data", "dashboards_read"], "mcp_all", "mcp_all"),
+        (["logs_read_data", "dashboards_read"], "openid mcp_all", "openid mcp_all"),
+        (["tools.read"], "mcp_allowed", "tools.read mcp_allowed"),
+    ],
 )
-async def test_managed_authorize_retains_the_callers_previous_grant(
-    jwt_oauth_identity, monkeypatch, prior_scopes, expected
-):
+async def test_managed_authorize_retains_the_previous_grant_except_for_a_wildcard_request(
+    jwt_oauth_identity: tuple["JWTHandler", "RSAPrivateKey"],
+    monkeypatch: pytest.MonkeyPatch,
+    prior_scopes: list[str] | None,
+    scope: str,
+    expected: str,
+) -> None:
     from types import SimpleNamespace
     from urllib.parse import parse_qs, urlsplit
 
@@ -15029,7 +15041,7 @@ async def test_managed_authorize_retains_the_callers_previous_grant(
         server,
         "scope-client",
         "http://127.0.0.1:9/cb",
-        scope="tools.write",
+        scope=scope,
         code_challenge="challenge",
         code_challenge_method="S256",
     )
@@ -15298,6 +15310,7 @@ async def test_connect_requires_the_requested_vendor_grant(monkeypatch, granted,
 
 
 _SLACK_SCOPES: Final = frozenset(("channels:read", "chat:write", "files:write"))
+_DATADOG_EXPANSION: Final = ("logs_read_index_data", "dashboards_read", "mcp_read", "mcp_write")
 _COMMA_NAMED_SCOPES: Final = frozenset(("files:read", "files:read,write"))
 
 
@@ -15316,6 +15329,10 @@ _COMMA_NAMED_SCOPES: Final = frozenset(("files:read", "files:read,write"))
         (("read", "write"), ("read", "write"), frozenset[str](), True),
         ((), ("read",), frozenset(("read",)), False),
         ((), (), frozenset[str](), True),
+        (_DATADOG_EXPANSION, ("mcp_all",), frozenset[str](), True),
+        (("channels:read,chat:write",), ("mcp_all", "channels:read"), _SLACK_SCOPES, True),
+        ((), ("mcp_all",), frozenset[str](), False),
+        (_DATADOG_EXPANSION, ("mcp_all", "admin"), frozenset[str](), False),
     ],
 )
 def test_grant_covers_scopes_splits_a_lone_token_only_into_known_scopes(