diff --git a/sqlspec/extensions/litestar/plugin.py b/sqlspec/extensions/litestar/plugin.py
index 8934872cf..9061e3720 100644
--- a/sqlspec/extensions/litestar/plugin.py
+++ b/sqlspec/extensions/litestar/plugin.py
@@ -399,7 +399,11 @@ def store_sqlspec_in_state() -> None:
         if self._enable_sqlcommenter_middleware:
             new_middlewares.append(DefineMiddleware(SQLCommenterMiddleware))
         if new_middlewares:
-            app_config.middleware = [*(app_config.middleware or []), *new_middlewares]
+            # Prepend so correlation context is established at the outer boundary of the
+            # pipeline. Appending makes these the innermost middleware, so a request
+            # rejected earlier (auth, CORS, rate limiting) never reaches them and its
+            # access log and error hooks have no correlation ID.
+            app_config.middleware = [*new_middlewares, *(app_config.middleware or [])]
 
         log_with_context(
             logger,
diff --git a/tests/integration/extensions/litestar/test_correlation_middleware.py b/tests/integration/extensions/litestar/test_correlation_middleware.py
index 380256cc9..c1438c371 100644
--- a/tests/integration/extensions/litestar/test_correlation_middleware.py
+++ b/tests/integration/extensions/litestar/test_correlation_middleware.py
@@ -1,6 +1,8 @@
-from typing import Any, cast
+from typing import TYPE_CHECKING, Any, cast
 
 from litestar import Litestar, get
+from litestar.middleware import AbstractMiddleware, DefineMiddleware
+from litestar.response.base import ASGIResponse
 from litestar.testing import TestClient
 
 from sqlspec import SQLSpec
@@ -9,6 +11,9 @@
 from sqlspec.extensions.litestar import SQLSpecPlugin
 from sqlspec.utils.correlation import CorrelationContext
 
+if TYPE_CHECKING:
+    from litestar.types import Receive, Scope, Send
+
 
 def setup_function() -> None:
     """Clear correlation context before each test to prevent pollution."""
@@ -99,3 +104,28 @@ def test_correlation_middleware_auto_detection_can_be_disabled() -> None:
 
         response = client.get("/correlation", headers={"X-Custom-ID": "custom-value"})
         assert response.json()["correlation_id"] == "custom-value"
+
+
+def test_correlation_middleware_runs_before_user_middleware() -> None:
+    """A request rejected by user middleware still carries correlation context."""
+    observed: dict[str, str | None] = {}
+
+    class RejectingMiddleware(AbstractMiddleware):
+        async def __call__(self, scope: "Scope", receive: "Receive", send: "Send") -> None:
+            observed["correlation_id"] = CorrelationContext.get()
+            await ASGIResponse(body=b'{"detail":"unauthorized"}', status_code=401)(scope, receive, send)
+
+    extension_config = cast("ExtensionConfigs", {"litestar": {"enable_correlation_middleware": True}})
+    spec = SQLSpec()
+    spec.add_config(SqliteConfig(connection_config={"database": ":memory:"}, extension_config=extension_config))
+    app = Litestar(
+        route_handlers=[correlation_handler],
+        plugins=[SQLSpecPlugin(sqlspec=spec)],
+        middleware=[DefineMiddleware(RejectingMiddleware)],
+    )
+
+    with TestClient(app) as client:
+        response = client.get("/correlation", headers={"X-Request-ID": "abc-123"})
+
+    assert response.status_code == 401
+    assert observed["correlation_id"] == "abc-123"