diff --git a/custom_components/reflex_clerk_api/clerk_provider.py b/custom_components/reflex_clerk_api/clerk_provider.py
index eccc235..0952524 100644
--- a/custom_components/reflex_clerk_api/clerk_provider.py
+++ b/custom_components/reflex_clerk_api/clerk_provider.py
@@ -59,6 +59,8 @@ class ClerkState(rx.State):
         "nbf": {"essential": True},
         # "azp": {"essential": False, "values": ["http://localhost:3000", "https://example.com"]},
     }
+    _jwt_validate_leeway_seconds: ClassVar[int] = 60
+    """Clock-skew leeway (seconds) for validating JWT claims like exp/nbf."""
 
     @classmethod
     def register_dependent_handler(cls, handler: EventCallback) -> None:
@@ -85,6 +87,29 @@ def set_claims_options(cls, claims_options: dict[str, Any]) -> None:
         """Set the claims options for the JWT claims validation."""
         cls._claims_options = claims_options
 
+    @classmethod
+    def set_jwt_validate_leeway_seconds(cls, seconds: int) -> None:
+        """Set clock-skew leeway (seconds) for JWT exp/nbf validation.
+
+        Default is 60 seconds. Increase if you see intermittent ExpiredTokenError
+        due to clock drift between Clerk servers and your backend.
+
+        Args:
+            seconds: Non-negative integer, max 3600 (1 hour).
+
+        Raises:
+            ValueError: If seconds is negative or exceeds 3600.
+        """
+        if not isinstance(seconds, int) or isinstance(seconds, bool) or seconds < 0:
+            raise ValueError(
+                f"jwt_validate_leeway_seconds must be a non-negative integer, got {seconds!r}"
+            )
+        if seconds > 3600:
+            raise ValueError(
+                f"jwt_validate_leeway_seconds exceeds maximum of 3600 (1 hour), got {seconds}"
+            )
+        cls._jwt_validate_leeway_seconds = seconds
+
     @property
     def client(self) -> clerk_backend_api.Clerk:
         if self._client is None:
@@ -116,9 +141,13 @@ async def set_clerk_session(self, token: str) -> EventType:
             return ClerkState.clear_clerk_session
         try:
             # Validate the token according to the claim options (e.g. iss, exp, nbf, azp.)
-            decoded.validate()
-        except (jose_errors.InvalidClaimError, jose_errors.MissingClaimError) as e:
-            logging.warning(f"JWT token is invalid: {e}")
+            decoded.validate(leeway=self._jwt_validate_leeway_seconds)
+        except (
+            jose_errors.ExpiredTokenError,
+            jose_errors.InvalidClaimError,
+            jose_errors.MissingClaimError,
+        ) as e:
+            logging.warning(f"JWT token validation failed: {type(e).__name__}: {e}")
             return ClerkState.clear_clerk_session
 
         async with self:
@@ -364,7 +393,7 @@ def add_imports(
     ) -> rx.ImportDict:
         addl_imports: rx.ImportDict = {
             "@clerk/clerk-react": ["useAuth"],
-            "react": ["useContext", "useEffect"],
+            "react": ["useContext", "useEffect", "useRef"],
             "$/utils/context": ["EventLoopContext"],
             "$/utils/state": ["ReflexEvent"],
         }
@@ -375,28 +404,73 @@ def add_custom_code(self) -> list[str]:
 
         return [
             """
-function ClerkSessionSynchronizer({ children }) {
-  const { getToken, isLoaded, isSignedIn } = useAuth()
-  const [ addEvents, connectErrors ] = useContext(EventLoopContext)
-
-  useEffect(() => {
-      if (isLoaded && !!addEvents) {
-        if (isSignedIn) {
-          getToken().then(token => {
-            addEvents([ReflexEvent("%s.set_clerk_session", {token})])
-          })
-        } else {
-          addEvents([ReflexEvent("%s.clear_clerk_session")])
-        }
-      }
-  }, [isSignedIn])
+function ClerkSessionSynchronizer({{ children }}) {{
+  const {{ getToken, isLoaded, isSignedIn }} = useAuth()
+  const [ addEvents ] = useContext(EventLoopContext)
+  // Tracks the last *successfully dispatched* (state, addEvents) pair. Only
+  // updated after a confirmed dispatch so transient token-fetch failures don't
+  // poison the dedupe and prevent later retries.
+  const lastSentRef = useRef({{ stateKey: null, addEvents: null }})
+  // Incremented on every effect run with new desired state. In-flight token
+  // fetches check this on resolve and bail if a newer effect has superseded
+  // them - prevents stale set_clerk_session dispatches after sign-out.
+  const requestIdRef = useRef(0)
+
+  useEffect(() => {{
+      // Wait for all dependencies to be ready.
+      if (!isLoaded || !addEvents) return
+
+      // Deduplicate rapid calls, but remain reconnect-safe:
+      // addEvents identity changes across websocket reconnects, so include it in the key.
+      const stateKey = isSignedIn ? "signed_in" : "signed_out"
+      if (
+        lastSentRef.current?.stateKey === stateKey &&
+        lastSentRef.current?.addEvents === addEvents
+      ) return
+
+      const myRequestId = ++requestIdRef.current
+
+      if (!isSignedIn) {{
+        // Always run the sign-out path immediately. Any in-flight token fetch
+        // will see myRequestId !== requestIdRef.current on resolve and drop.
+        addEvents([ReflexEvent("{state}.clear_clerk_session")])
+        lastSentRef.current = {{ stateKey, addEvents }}
+        return
+      }}
+
+      // isSignedIn: try to get a fresh token. Retry once after a short delay
+      // on transient failures before clearing the backend session - clearing
+      // prematurely forces a logout while Clerk is still signed in.
+      // Prefer skipCache (avoids near-expiry cached tokens); fall back if the
+      // installed Clerk version doesn't support that option.
+      const fetchToken = () =>
+        getToken({{ skipCache: true }}).catch(() => getToken())
+      fetchToken()
+        .catch(() => new Promise(resolve => setTimeout(resolve, 500)).then(fetchToken))
+        .then(token => {{
+          // Drop if a newer effect run (e.g., sign-out) has superseded us.
+          if (myRequestId !== requestIdRef.current) return
+          if (token) {{
+            addEvents([ReflexEvent("{state}.set_clerk_session", {{token}})])
+            lastSentRef.current = {{ stateKey, addEvents }}
+          }} else {{
+            // Final failure: clear backend session but leave lastSentRef
+            // unchanged so the next trigger (reconnect, sign-in toggle, etc.)
+            // re-attempts the sync instead of being deduped away.
+            addEvents([ReflexEvent("{state}.clear_clerk_session")])
+          }}
+        }})
+        .catch(() => {{
+          if (myRequestId !== requestIdRef.current) return
+          addEvents([ReflexEvent("{state}.clear_clerk_session")])
+        }})
+  }}, [isLoaded, isSignedIn, addEvents, getToken])
 
   return (
-      <>{children}</>
+      <>{{children}}</>
   )
-}
-"""
-            % (clerk_state_name, clerk_state_name)
+}}
+""".format(state=clerk_state_name)
         ]
 
 
diff --git a/pyproject.toml b/pyproject.toml
index 85bc7d8..0144cb0 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -47,6 +47,7 @@ homepage = "https://reflex-clerk-api-demo.adventuresoftim.com"
 
 [tool.pytest.ini_options]
 # addopts = "--headed"
+pythonpath = ["custom_components"]
 
 [tool.pyright]
 venvPath = "."
diff --git a/tests/test_clerk_provider_unit.py b/tests/test_clerk_provider_unit.py
new file mode 100644
index 0000000..9e77572
--- /dev/null
+++ b/tests/test_clerk_provider_unit.py
@@ -0,0 +1,52 @@
+import asyncio
+
+import authlib.jose.errors as jose_errors
+
+
+def test_set_clerk_session_expired_token_clears(monkeypatch):
+    """Expired tokens should not crash the handler; they should clear session."""
+    # Import inside the test so the module is importable in different test layouts.
+    # We need the actual module object (not just ClerkState) to monkeypatch jwt.decode
+    # where it's used. importlib is required because reflex_clerk_api.clerk_provider
+    # resolves to the function via __init__.py re-exports.
+    import importlib
+
+    clerk_provider_module = importlib.import_module("reflex_clerk_api.clerk_provider")
+    from reflex_clerk_api.clerk_provider import ClerkState
+
+    # Instantiate state in a framework-safe way for tests.
+    state = ClerkState(_reflex_internal_init=True)  # pyright: ignore[reportCallIssue]
+
+    async def fake_get_jwk_keys(self):
+        return {}
+
+    monkeypatch.setattr(ClerkState, "_get_jwk_keys", fake_get_jwk_keys, raising=True)
+
+    validate_calls: dict[str, object] = {}
+
+    class FakeClaims:
+        def validate(self, leeway=None):
+            validate_calls["leeway"] = leeway
+            raise jose_errors.ExpiredTokenError()
+
+    monkeypatch.setattr(
+        clerk_provider_module.jwt,
+        "decode",
+        lambda *args, **kwargs: FakeClaims(),
+        raising=True,
+    )
+
+    result = asyncio.run(
+        ClerkState.set_clerk_session.fn(state, token="fake")  # pyright: ignore[reportAttributeAccessIssue]
+    )
+    assert validate_calls["leeway"] == 60
+    assert result == ClerkState.clear_clerk_session
+
+
+def test_clerk_session_synchronizer_js_contains_reconnect_safe_deps_and_skipcache():
+    """String-based regression test for the generated JS."""
+    from reflex_clerk_api.clerk_provider import ClerkSessionSynchronizer
+
+    js = ClerkSessionSynchronizer.create().add_custom_code()[0]
+    assert "[isLoaded, isSignedIn, addEvents, getToken]" in js
+    assert "skipCache: true" in js