diff --git a/site/src/index.tsx b/site/src/index.tsx
index 59ab9e6264..220e5370f2 100644
--- a/site/src/index.tsx
+++ b/site/src/index.tsx
@@ -11,6 +11,22 @@ console.info(`      -#######          +######-      ########+       ##########
      .########+        -########.     #########+      ##########  ####    .####   ###########
 `);
 
+// After a redeploy, the SPA still holds old chunk filenames in memory.
+// Navigating to a lazy-loaded route will try to fetch a chunk that no
+// longer exists (the content hash changed), crashing the app. Vite fires
+// this event whenever a dynamic-import preload fails. We catch it and
+// silently reload so the browser fetches a fresh index.html with the new
+// chunk names. A sessionStorage guard prevents infinite reload loops.
+window.addEventListener("vite:preloadError", () => {
+	const key = "preload-reload";
+	const last = sessionStorage.getItem(key);
+	const now = Date.now();
+	if (!last || now - Number(last) > 10_000) {
+		sessionStorage.setItem(key, String(now));
+		window.location.reload();
+	}
+});
+
 const element = document.getElementById("root");
 if (element === null) {
 	throw new Error("root element is null");