diff --git a/web/lib/prerender-cache-key.ts b/web/lib/prerender-cache-key.ts
new file mode 100644
index 00000000..30d0e0e4
--- /dev/null
+++ b/web/lib/prerender-cache-key.ts
@@ -0,0 +1,19 @@
+// Next.js 16.3.8 scopes response-cache keys to the route that owns them: a
+// prerendered page is looked up as
+//
+//   /route-cache/<ROUTE_KIND>/<sha256 of the source route>/$<page path>
+//
+// (see next/dist/server/lib/route-cache-key.js). The OpenNext static-assets
+// incremental cache still stores build-time prerenders by plain page path
+// (<build id>/<page path>.cache), so the scoped key never matches a file and
+// every page falls through to a runtime render — which 500s for pages that
+// cannot render in the Workers runtime.
+//
+// This maps a scoped key back to the plain page path the cache is stored under.
+// Keys in any other shape (older Next versions, fetch cache) pass through.
+const ROUTE_CACHE_KEY = /^\/?route-cache\/[^/]+\/[0-9a-f]{64}\/\$(.*)$/;
+
+export function toPrerenderCacheKey(key: string): string {
+  const match = ROUTE_CACHE_KEY.exec(key);
+  return match ? match[1] : key;
+}
diff --git a/web/lib/test/prerender-cache-key.test.ts b/web/lib/test/prerender-cache-key.test.ts
new file mode 100644
index 00000000..55702a1a
--- /dev/null
+++ b/web/lib/test/prerender-cache-key.test.ts
@@ -0,0 +1,40 @@
+import { createHash } from 'node:crypto';
+
+import { describe, expect, it } from 'vitest';
+// The real key builder, so this fails if a Next upgrade changes the key shape
+// again instead of silently missing the prerender cache in production.
+import { getRouteCacheKey } from 'next/dist/server/lib/route-cache-key';
+import type { RouteKind } from 'next/dist/server/route-kind';
+
+import { toPrerenderCacheKey } from '../prerender-cache-key';
+
+// RouteKind is a const enum, which isolatedModules cannot import as a value.
+const appPage = (page: string) => ({ kind: 'APP_PAGE' as RouteKind, sourceRoute: page });
+
+describe('toPrerenderCacheKey', () => {
+  it('maps a static page key to its page path', () => {
+    expect(toPrerenderCacheKey(getRouteCacheKey('/flows', appPage('/flows/page')))).toBe('/flows');
+  });
+
+  it('maps a generateStaticParams page key to its concrete path', () => {
+    const key = getRouteCacheKey('/docs/introduction', appPage('/docs/[slug]/page'));
+    expect(toPrerenderCacheKey(key)).toBe('/docs/introduction');
+  });
+
+  it('maps the root page to /index, matching the stored index.cache', () => {
+    expect(toPrerenderCacheKey(getRouteCacheKey('/', appPage('/page')))).toBe('/index');
+  });
+
+  it('accepts the documented key shape literally', () => {
+    const hash = createHash('sha256').update('/flows/page').digest('hex');
+    expect(toPrerenderCacheKey(`/route-cache/APP_PAGE/${hash}/$/flows`)).toBe('/flows');
+  });
+
+  it('passes through keys that are not route-scoped', () => {
+    expect(toPrerenderCacheKey('/flows')).toBe('/flows');
+    expect(toPrerenderCacheKey('docs/introduction')).toBe('docs/introduction');
+    expect(toPrerenderCacheKey('44fe800491717aa4131a86c6f5e0985967ffe4edf6c95db62d6512d94188fd5f')).toBe(
+      '44fe800491717aa4131a86c6f5e0985967ffe4edf6c95db62d6512d94188fd5f',
+    );
+  });
+});
diff --git a/web/open-next.config.ts b/web/open-next.config.ts
index f52cef0b..f2634fa7 100644
--- a/web/open-next.config.ts
+++ b/web/open-next.config.ts
@@ -1,5 +1,8 @@
 import { defineCloudflareConfig } from "@opennextjs/cloudflare";
 import staticAssetsIncrementalCache from "@opennextjs/cloudflare/overrides/incremental-cache/static-assets-incremental-cache";
+import type { IncrementalCache } from "@opennextjs/aws/types/overrides.js";
+
+import { toPrerenderCacheKey } from "./lib/prerender-cache-key";
 
 // Marketing/docs site: static + SSG pages (docs MDX is read from disk at BUILD
 // time) plus a few dynamic routes and the PostHog proxy middleware.
@@ -10,6 +13,18 @@ import staticAssetsIncrementalCache from "@opennextjs/cloudflare/overrides/incre
 // the filesystem, and the Cloudflare Workers runtime stubs Node `fs`
 // (unenv) — so any runtime re-render of a docs page would fail. Serving the
 // prerendered output from assets avoids that entirely. No R2/KV needed.
+//
+// Next 16.3.8 asks for prerendered pages under a route-scoped key the
+// static-assets cache does not store them under, so translate the key back to
+// the page path before the lookup. Without this every page misses the cache.
+const incrementalCache: IncrementalCache = {
+  name: staticAssetsIncrementalCache.name,
+  get: (key, cacheType) => staticAssetsIncrementalCache.get(toPrerenderCacheKey(key), cacheType),
+  set: (key, value, cacheType) => staticAssetsIncrementalCache.set(toPrerenderCacheKey(key), value, cacheType),
+  // Read-only cache: delete takes no key and only logs.
+  delete: () => staticAssetsIncrementalCache.delete(),
+};
+
 export default defineCloudflareConfig({
-  incrementalCache: staticAssetsIncrementalCache,
+  incrementalCache,
 });