diff --git a/src/create-with-winter-spec.ts b/src/create-with-winter-spec.ts
index 229a28c..c57ee2b 100644
--- a/src/create-with-winter-spec.ts
+++ b/src/create-with-winter-spec.ts
@@ -76,13 +76,13 @@ export const createWithWinterSpec = <const GS extends GlobalSpec>(
             // error response that does not match the routeSpec's response shape
             serializeResponse(globalSpec, routeSpec, false),
             ...(globalSpec.beforeAuthMiddleware ?? []),
+            withResponseObjectCheck,
             firstAuthMiddlewareThatSucceeds(
               authMiddlewares,
               onMultipleAuthMiddlewareFailures
             ),
             ...(globalSpec.afterAuthMiddleware ?? []),
             ...(routeSpec.middleware ?? []),
-            withResponseObjectCheck,
             withMethods(routeSpec.methods),
             withInputValidation({
               supportedArrayFormats: globalSpec.supportedArrayFormats ?? [
diff --git a/src/middleware/with-response-object-check.ts b/src/middleware/with-response-object-check.ts
index 9f8cae0..6475c5b 100644
--- a/src/middleware/with-response-object-check.ts
+++ b/src/middleware/with-response-object-check.ts
@@ -1,14 +1,19 @@
-import { ResponseValidationError } from "./http-exceptions.js"
 import { Middleware } from "./types.js"
-import { RouteSpec } from "src/types/route-spec.js"
 
-export const withResponseObjectCheck: Middleware<
-  { routeSpec: RouteSpec<any> },
-  {}
-> = async (req, ctx, next) => {
+export const withResponseObjectCheck: Middleware = async (req, ctx, next) => {
   const rawResponse = await next(req, ctx)
 
-  if (typeof rawResponse === "object" && !(rawResponse instanceof Response)) {
+  const canSerializeToResponse =
+    rawResponse !== null &&
+    typeof rawResponse === "object" &&
+    "serializeToResponse" in rawResponse &&
+    typeof rawResponse.serializeToResponse === "function"
+
+  if (
+    typeof rawResponse === "object" &&
+    !(rawResponse instanceof Response) &&
+    !canSerializeToResponse
+  ) {
     throw new Error(
       "Use ctx.json({...}) instead of returning an object directly."
     )
diff --git a/src/types/winter-spec.ts b/src/types/winter-spec.ts
index ba5adac..c21352d 100644
--- a/src/types/winter-spec.ts
+++ b/src/types/winter-spec.ts
@@ -1,6 +1,7 @@
 import type { Middleware } from "src/middleware/types.js"
 import {
   createWinterSpecRequest,
+  type SerializableToResponse,
   type WinterSpecRouteFn,
   type WinterSpecRouteParams,
   WinterSpecRequest,
@@ -10,6 +11,7 @@ import type { ReadonlyDeep } from "type-fest"
 import { wrapMiddlewares } from "src/create-with-winter-spec.js"
 import { getDefaultContext } from "./context.js"
 import { Server } from "node:http"
+import { z } from "zod"
 
 export type WinterSpecRouteMatcher = (pathname: string) =>
   | {
@@ -126,11 +128,44 @@ export function makeRequestAgainstWinterSpec(
       return await handle404(winterSpecRequest, getDefaultContext())
     }
 
-    return wrapMiddlewares(
+    const rawResponse = await wrapMiddlewares(
       options.middleware ?? [],
       routeFn,
       winterSpecRequest,
       getDefaultContext()
     )
+
+    return serializeMakeRequestMiddlewareResponse(rawResponse)
+  }
+}
+
+function isSerializableToResponse(
+  response: unknown
+): response is SerializableToResponse {
+  return (
+    response !== null &&
+    typeof response === "object" &&
+    "serializeToResponse" in response &&
+    typeof response.serializeToResponse === "function"
+  )
+}
+
+function serializeMakeRequestMiddlewareResponse(
+  response: Response | SerializableToResponse
+): Response {
+  if (response instanceof Response) {
+    return response
   }
+
+  if (isSerializableToResponse(response)) {
+    return response.serializeToResponse(z.any())
+  }
+
+  if (response !== null && typeof response === "object") {
+    throw new Error(
+      "Invalid response object. Use ctx.json({...}) instead of returning an object directly."
+    )
+  }
+
+  return response as Response
 }
diff --git a/tests/bundling/make-request/make-request.test.ts b/tests/bundling/make-request/make-request.test.ts
index 8ceaf6b..200fa84 100644
--- a/tests/bundling/make-request/make-request.test.ts
+++ b/tests/bundling/make-request/make-request.test.ts
@@ -57,6 +57,45 @@ test.serial("custom middleware works", async (t) => {
   t.is(await response.text(), "intercepted")
 })
 
+test.serial("custom middleware can return ctx.json", async (t) => {
+  const bundle = await createAndLoadBundle(t)
+  t.truthy(bundle.makeRequest)
+
+  const response = await bundle.makeRequest(
+    new Request(new URL("https://example.com/health")),
+    {
+      middleware: [
+        (_req, ctx: any) => {
+          return ctx.json({ ok: true })
+        },
+      ],
+    }
+  )
+  t.is(response.status, 200)
+  t.deepEqual(await response.json(), { ok: true })
+})
+
+test.serial("custom middleware rejects raw object responses", async (t) => {
+  const bundle = await createAndLoadBundle(t)
+  t.truthy(bundle.makeRequest)
+
+  const error = await t.throwsAsync(() =>
+    bundle.makeRequest(new Request(new URL("https://example.com/health")), {
+      middleware: [
+        () => {
+          return { ok: true } as any
+        },
+      ],
+    })
+  )
+
+  t.true(
+    error?.message.includes(
+      "Use ctx.json({...}) instead of returning an object directly"
+    )
+  )
+})
+
 test.serial("can make request when hosted on subpath", async (t) => {
   const bundle = await createAndLoadBundle(t)
 
diff --git a/tests/errors/do-not-allow-raw-json.test.ts b/tests/errors/do-not-allow-raw-json.test.ts
index 8682796..073a94f 100644
--- a/tests/errors/do-not-allow-raw-json.test.ts
+++ b/tests/errors/do-not-allow-raw-json.test.ts
@@ -37,3 +37,43 @@ test("should throw an error when responding with raw JSON", async (t) => {
     )
   )
 })
+
+test("should throw an error when middleware responds with raw JSON", async (t) => {
+  const { axios } = await getTestRoute(t, {
+    globalSpec: {
+      authMiddleware: {},
+      beforeAuthMiddleware: [
+        async (req, ctx, next) => {
+          try {
+            return await next(req, ctx)
+          } catch (e: any) {
+            return Response.json({ error: e.message }, { status: 500 })
+          }
+        },
+      ],
+    },
+    routeSpec: {
+      methods: ["GET"],
+      jsonBody: z.any(),
+      jsonResponse: z.any(),
+      middleware: [
+        async () => {
+          return { foo: "bar" } as any
+        },
+      ],
+    },
+    routePath: "/",
+    routeFn: (req, ctx) => {
+      return ctx.json({ ok: true })
+    },
+  })
+
+  const { data } = await axios.get("/", {
+    validateStatus: () => true,
+  })
+  t.true(
+    data.error.includes(
+      "Use ctx.json({...}) instead of returning an object directly"
+    )
+  )
+})