diff --git a/.changeset/large-lobsters-grin.md b/.changeset/large-lobsters-grin.md
new file mode 100644
index 0000000000..41d1eb914e
--- /dev/null
+++ b/.changeset/large-lobsters-grin.md
@@ -0,0 +1,50 @@
+---
+"@react-router/dev": minor
+---
+
+Automatic types for future flags
+
+Some future flags alter the way types should work in React Router.
+Previously, you had to remember to manually opt-in to the new types.
+
+For example, for `unstable_middleware`:
+
+```ts
+// react-router.config.ts
+
+// Step 1: Enable middleware
+export default {
+  future: {
+    unstable_middleware: true,
+  },
+};
+
+// Step 2: Enable middleware types
+declare module "react-router" {
+  interface Future {
+    unstable_middleware: true; // 👈 Enable middleware types
+  }
+}
+```
+
+It was up to you to keep the runtime future flags synced with the types for those future flags.
+This was confusing and error-prone.
+
+Now, React Router will automatically enable types for future flags.
+That means you only need to specify the runtime future flag:
+
+```ts
+// react-router.config.ts
+
+// Step 1: Enable middleware
+export default {
+  future: {
+    unstable_middleware: true,
+  },
+};
+
+// No step 2! That's it!
+```
+
+Behind the scenes, React Router will generate the corresponding `declare module` into `.react-router/types`.
+Currently this is done in `.react-router/types/+register.ts` but this is an implementation detail that may change in the future.
diff --git a/packages/react-router-dev/typegen/index.ts b/packages/react-router-dev/typegen/index.ts
index 05e2f1e0a1..4168aa9bf8 100644
--- a/packages/react-router-dev/typegen/index.ts
+++ b/packages/react-router-dev/typegen/index.ts
@@ -31,21 +31,23 @@ export async function watch(
   await writeAll(ctx);
   logger?.info(pc.green("generated types"), { timestamp: true, clear: true });
 
-  ctx.configLoader.onChange(async ({ result, routeConfigChanged }) => {
-    if (!result.ok) {
-      logger?.error(pc.red(result.error), { timestamp: true, clear: true });
-      return;
-    }
+  ctx.configLoader.onChange(
+    async ({ result, configChanged, routeConfigChanged }) => {
+      if (!result.ok) {
+        logger?.error(pc.red(result.error), { timestamp: true, clear: true });
+        return;
+      }
 
-    ctx.config = result.value;
-    if (routeConfigChanged) {
-      await writeAll(ctx);
-      logger?.info(pc.green("regenerated types"), {
-        timestamp: true,
-        clear: true,
-      });
+      ctx.config = result.value;
+      if (configChanged || routeConfigChanged) {
+        await writeAll(ctx);
+        logger?.info(pc.green("regenerated types"), {
+          timestamp: true,
+          clear: true,
+        });
+      }
     }
-  });
+  );
 
   return {
     close: async () => await ctx.configLoader.close(),
@@ -103,6 +105,10 @@ function register(ctx: Context) {
       interface Register {
         params: Params;
       }
+
+      interface Future {
+        unstable_middleware: ${ctx.config.future.unstable_middleware}
+      }
     }
   `;
 
diff --git a/playground/middleware/react-router.config.ts b/playground/middleware/react-router.config.ts
index 2cb7be3730..8ebd8738ed 100644
--- a/playground/middleware/react-router.config.ts
+++ b/playground/middleware/react-router.config.ts
@@ -1,11 +1,4 @@
 import type { Config } from "@react-router/dev/config";
-import type { Future } from "react-router";
-
-declare module "react-router" {
-  interface Future {
-    unstable_middleware: true;
-  }
-}
 
 export default {
   future: {