modelcontextprotocol
diff --git a/src/mcp/client/auth/oauth2.py b/src/mcp/client/auth/oauth2.py
@@ -5,6 +5,7 @@
 
 import base64
 import hashlib
+import inspect
 import logging
 import secrets
 import string
@@ -551,6 +552,38 @@ async def _initialize(self) -> None:
         """Load stored tokens and client info."""
         self.context.current_tokens = await self.context.storage.get_tokens()
         self.context.client_info = await self.context.storage.get_client_info()
+        # Compute the absolute expiry time from the loaded token's relative
+        # `expires_in`. Without this, `is_token_valid()` short-circuits to True
+        # when `token_expiry_time` is None and the refresh-on-expiry path in
+        # `async_auth_flow` never fires — every process restart sends an
+        # expired access_token, gets a 401, and lands in the full re-auth
+        # branch. Mirrors what `set_tokens` does on the write path.
+        if self.context.current_tokens is not None:
+            self.context.update_token_expiry(self.context.current_tokens)
+        # Optionally load OAuth metadata from storage. Some downstream storage
+        # implementations (e.g. ones persisting `.meta.json` from server
+        # discovery) implement this; SDK-provided storages do not, so the
+        # `getattr` guard keeps this a no-op when absent.
+        #
+        # Without this, `_refresh_token` falls back to `urljoin(base, "/token")`
+        # which gives the wrong endpoint for any IdP that mounts its token
+        # endpoint at a non-root path (Hydra/Ory-style: /oauth/token, Auth0:
+        # /oauth/token, Keycloak: /protocol/openid-connect/token, etc.) and
+        # silently 404s the refresh grant.
+        loader = getattr(self.context.storage, "load_oauth_metadata", None)
+        if callable(loader):
+            try:
+                meta = loader()
+                if inspect.iscoroutine(meta):
+                    meta = await meta
+                if meta is not None:
+                    self.context.oauth_metadata = meta  # type: ignore[assignment]
-                    self.context.oauth_metadata = meta  # type: ignore[assignment]
+                    self.context.oauth_metadata = (
+                        meta if isinstance(meta, OAuthMetadata) else OAuthMetadata.model_validate(meta)
+                    )
-                    self.context.oauth_metadata = meta  # type: ignore[assignment]
+                    self.context.oauth_metadata = (
+                        meta if isinstance(meta, OAuthMetadata) else OAuthMetadata.model_validate(meta)
+                    )
+            except Exception:
+                # Storage implementations are user-provided; a misbehaving
+                # metadata loader must not break auth initialization. The
+                # 401-handling path will populate `oauth_metadata` via server
+                # discovery as a fallback.
+                pass
         self._initialized = True
 
     def _add_auth_header(self, request: httpx2.Request) -> None:

diff --git a/tests/client/test_auth.py b/tests/client/test_auth.py
@@ -636,6 +636,114 @@ async def test_refresh_token_request(self, oauth_provider: OAuthClientProvider,
         assert "client_id=test_client" in content
         assert "client_secret=test_secret" in content
 
+    @pytest.mark.anyio
+    async def test_initialize_computes_token_expiry_time(self, oauth_provider: OAuthClientProvider, valid_tokens: OAuthToken):
+        """`_initialize` must compute `context.token_expiry_time` from the loaded
+        token's relative `expires_in` — otherwise `is_token_valid()` short-
+        circuits to True and refresh-on-expiry never fires after a process
+        restart (see https://github.com/modelcontextprotocol/python-sdk/issues/3250)."""
+        inner_storage: MockTokenStorage = oauth_provider.context.storage  # type: ignore[assignment]
+        await inner_storage.set_tokens(valid_tokens)
+        await inner_storage.set_client_info(
+            OAuthClientInformationFull(
+                client_id="test_client",
+                redirect_uris=[AnyUrl("http://localhost:3030/callback")],
+                token_endpoint_auth_method="none",
+            )
+        )
+
+        # token_expiry_time should be None before init, populated after init.
+        assert oauth_provider.context.token_expiry_time is None
+        await oauth_provider._initialize()
+        # valid_tokens fixture has expires_in=3600
+        assert valid_tokens.expires_in is not None
+        expected = time.time() + valid_tokens.expires_in
+        assert oauth_provider.context.token_expiry_time is not None
+        assert abs(oauth_provider.context.token_expiry_time - expected) < 5
+        assert oauth_provider.context.is_token_valid()
+
+        # An immediately-expired token (clamped `expires_in=0` from
+        # `HermesTokenStorage`-style storage rewrite of a stale on-disk token)
+        # must produce an invalid state — not short-circuit to True.
+        class _ExpiredStorage(MockTokenStorage):
+            async def get_tokens(self) -> OAuthToken | None:
+                token = await super().get_tokens()
+                if token is not None:
+                    return token.model_copy(update={"expires_in": 0})
+                return None
+
+        wrapped = _ExpiredStorage()
+        await wrapped.set_tokens(valid_tokens)
+        client_info = await inner_storage.get_client_info()
+        assert client_info is not None
+        await wrapped.set_client_info(client_info)
+        oauth_provider.context.storage = wrapped  # type: ignore[assignment]
+        oauth_provider._initialized = False
+        oauth_provider.context.token_expiry_time = None
+        await oauth_provider._initialize()
+        assert oauth_provider.context.token_expiry_time is not None
+        assert oauth_provider.context.token_expiry_time <= time.time()
+        assert not oauth_provider.context.is_token_valid()
+
+    @pytest.mark.anyio
+    async def test_initialize_loads_oauth_metadata_from_storage(self, oauth_provider: OAuthClientProvider, valid_tokens: OAuthToken):
+        """`_initialize` must call `storage.load_oauth_metadata()` if the storage
+        implements it — otherwise `_refresh_token` falls back to
+        `urljoin(base, "/token")` which silently 404s against any IdP that
+        mounts its token endpoint at a non-root path (Hydra, Auth0, Keycloak)."""
+        canonical_meta = OAuthMetadata(
+            issuer=AnyHttpUrl("https://hydra.example.com/"),
+            authorization_endpoint=AnyHttpUrl("https://hydra.example.com/oauth2/auth"),
+            token_endpoint=AnyHttpUrl("https://hydra.example.com/oauth2/token"),
+            token_endpoint_auth_methods_supported=["none"],
+            response_types_supported=["code"],
+            grant_types_supported=["authorization_code", "refresh_token"],
+            code_challenge_methods_supported=["S256"],
+        )
+
+        class _MetadataStorage(MockTokenStorage):
+            def load_oauth_metadata(self) -> OAuthMetadata:
+                return canonical_meta
+
+        meta_storage = _MetadataStorage()
+        await meta_storage.set_tokens(valid_tokens)
+        await meta_storage.set_client_info(
+            OAuthClientInformationFull(
+                client_id="test_client",
+                redirect_uris=[AnyUrl("http://localhost:3030/callback")],
+                token_endpoint_auth_method="none",
+            )
+        )
+        oauth_provider.context.storage = meta_storage  # type: ignore[assignment]
+        oauth_provider._initialized = False
+
+        await oauth_provider._initialize()
+        assert oauth_provider.context.oauth_metadata is canonical_meta
+
+        # Verify the metadata is actually used by _refresh_token — without the
+        # patch, this would build `https://api.example.com/token` (404 for Hydra).
+        oauth_provider.context.current_tokens = valid_tokens
+        request = await oauth_provider._refresh_token()
+        assert str(request.url) == "https://hydra.example.com/oauth2/token"
+
+    @pytest.mark.anyio
+    async def test_initialize_metadata_loader_failure_is_non_fatal(self, oauth_provider: OAuthClientProvider, valid_tokens: OAuthToken):
+        """A misbehaving `load_oauth_metadata` must not break auth init — the
+        401-handling path will populate metadata via server discovery as a fallback."""
+        class _BrokenMetadataStorage(MockTokenStorage):
+            def load_oauth_metadata(self) -> OAuthMetadata:
+                raise RuntimeError("simulated storage failure")
+
+        broken = _BrokenMetadataStorage()
+        await broken.set_tokens(valid_tokens)
+        oauth_provider.context.storage = broken  # type: ignore[assignment]
+
+        # Should not raise — the try/except in _initialize swallows loader errors.
+        await oauth_provider._initialize()
+        assert oauth_provider.context.current_tokens is not None
+        assert oauth_provider.context.token_expiry_time is not None
+        assert oauth_provider.context.oauth_metadata is None
+
     @pytest.mark.anyio
     async def test_basic_auth_token_exchange(self, oauth_provider: OAuthClientProvider):
         """Test token exchange with client_secret_basic authentication."""