diff --git a/packages/astro/src/@types/astro.ts b/packages/astro/src/@types/astro.ts
index cc9c2054166a..67b89ba48f2e 100644
--- a/packages/astro/src/@types/astro.ts
+++ b/packages/astro/src/@types/astro.ts
@@ -2626,6 +2626,11 @@ export interface APIContext<
 	 */
 	redirect: AstroSharedContext['redirect'];
 
+	/**
+	 * TODO: docs
+	 */
+	reroute: AstroSharedContext['reroute'];
+
 	/**
 	 * An object that middlewares can use to store extra information related to the request.
 	 *
diff --git a/packages/astro/src/core/middleware/callMiddleware.ts b/packages/astro/src/core/middleware/callMiddleware.ts
index 5a0456680a6c..755291be39cb 100644
--- a/packages/astro/src/core/middleware/callMiddleware.ts
+++ b/packages/astro/src/core/middleware/callMiddleware.ts
@@ -43,13 +43,17 @@ import { AstroError, AstroErrorData } from '../errors/index.js';
 export async function callMiddleware(
 	onRequest: MiddlewareHandler,
 	apiContext: APIContext,
-	responseFunction: (reroutePayload?: ReroutePayload) => Promise<Response> | Response
+	responseFunction: (
+		apiContext: APIContext,
+		reroutePayload?: ReroutePayload
+	) => Promise<Response> | Response
 ): Promise<Response> {
 	let nextCalled = false;
 	let responseFunctionPromise: Promise<Response> | Response | undefined = undefined;
 	const next: MiddlewareNext = async (payload) => {
 		nextCalled = true;
-		responseFunctionPromise = responseFunction(payload);
+		// We need to pass the APIContext pass to `callMiddleware` because it can be mutated across middleware functions
+		responseFunctionPromise = responseFunction(apiContext, payload);
 		return responseFunctionPromise;
 	};
 
diff --git a/packages/astro/src/core/middleware/sequence.ts b/packages/astro/src/core/middleware/sequence.ts
index 5a0842d8f842..3782bc30befa 100644
--- a/packages/astro/src/core/middleware/sequence.ts
+++ b/packages/astro/src/core/middleware/sequence.ts
@@ -1,5 +1,6 @@
 import type { APIContext, MiddlewareHandler, ReroutePayload } from '../../@types/astro.js';
 import { defineMiddleware } from './index.js';
+import { AstroCookies } from '../cookies/cookies.js';
 
 // From SvelteKit: https://github.com/sveltejs/kit/blob/master/packages/kit/src/exports/hooks/sequence.js
 /**
@@ -10,12 +11,16 @@ export function sequence(...handlers: MiddlewareHandler[]): MiddlewareHandler {
 	const filtered = handlers.filter((h) => !!h);
 	const length = filtered.length;
 	if (!length) {
-		return defineMiddleware((context, next) => {
+		return defineMiddleware((_context, next) => {
 			return next();
 		});
 	}
 
 	return defineMiddleware((context, next) => {
+		/**
+		 * This variable is used to carry the rerouting payload across middleware functions.
+		 */
+		let carriedPayload: ReroutePayload | undefined = undefined;
 		return applyHandle(0, context);
 
 		function applyHandle(i: number, handleContext: APIContext) {
@@ -25,9 +30,26 @@ export function sequence(...handlers: MiddlewareHandler[]): MiddlewareHandler {
 			// doing a loop over all the `next` functions, and eventually we call the last `next` that returns the `Response`.
 			const result = handle(handleContext, async (payload: ReroutePayload) => {
 				if (i < length - 1) {
+					if (payload) {
+						let newRequest;
+						if (payload instanceof Request) {
+							newRequest = payload;
+						} else if (payload instanceof URL) {
+							newRequest = new Request(payload, handleContext.request);
+						} else {
+							newRequest = new Request(
+								new URL(payload, handleContext.url.origin),
+								handleContext.request
+							);
+						}
+						carriedPayload = payload;
+						handleContext.request = newRequest;
+						handleContext.url = new URL(newRequest.url);
+						handleContext.cookies = new AstroCookies(newRequest);
+					}
 					return applyHandle(i + 1, handleContext);
 				} else {
-					return next(payload);
+					return next(payload ?? carriedPayload);
 				}
 			});
 			return result;
diff --git a/packages/astro/src/core/render-context.ts b/packages/astro/src/core/render-context.ts
index bec6feba3a25..efada3e215a7 100644
--- a/packages/astro/src/core/render-context.ts
+++ b/packages/astro/src/core/render-context.ts
@@ -111,7 +111,7 @@ export class RenderContext {
 				statusText: 'Loop Detected',
 			});
 		}
-		const lastNext: MiddlewareNext = async (payload) => {
+		const lastNext = async (ctx: APIContext, payload?: ReroutePayload) => {
 			if (payload) {
 				if (this.pipeline.manifest.reroutingEnabled) {
 					try {
@@ -135,7 +135,7 @@ export class RenderContext {
 			}
 			switch (this.routeData.type) {
 				case 'endpoint':
-					return renderEndpoint(componentInstance as any, apiContext, serverLike, logger);
+					return renderEndpoint(componentInstance as any, ctx, serverLike, logger);
 				case 'redirect':
 					return renderRedirect(this);
 				case 'page': {
@@ -174,9 +174,7 @@ export class RenderContext {
 			}
 		};
 
-		const response = this.isRerouting
-			? await lastNext()
-			: await callMiddleware(middleware, apiContext, lastNext);
+		const response = await callMiddleware(middleware, apiContext, lastNext);
 		if (response.headers.get(ROUTE_TYPE_HEADER)) {
 			response.headers.delete(ROUTE_TYPE_HEADER);
 		}
diff --git a/packages/astro/test/fixtures/reroute/astro.config.mjs b/packages/astro/test/fixtures/reroute/astro.config.mjs
index af736916179e..6d20ec89a31d 100644
--- a/packages/astro/test/fixtures/reroute/astro.config.mjs
+++ b/packages/astro/test/fixtures/reroute/astro.config.mjs
@@ -4,5 +4,6 @@ import { defineConfig } from 'astro/config';
 export default defineConfig({
 	experimental: {
 		rerouting: true
-	}
+	},
+	site: "https://example.com"
 });
diff --git a/packages/astro/test/fixtures/reroute/src/middleware.js b/packages/astro/test/fixtures/reroute/src/middleware.js
new file mode 100644
index 000000000000..0cf03c1d7713
--- /dev/null
+++ b/packages/astro/test/fixtures/reroute/src/middleware.js
@@ -0,0 +1,33 @@
+import { sequence } from 'astro:middleware';
+
+let contextReroute = false;
+
+export const first = async (context, next) => {
+	if (context.url.pathname.includes('/auth')) {
+	}
+
+	return next();
+};
+
+export const second = async (context, next) => {
+	if (context.url.pathname.includes('/auth')) {
+		if (context.url.pathname.includes('/auth/dashboard')) {
+			contextReroute = true;
+			return await context.reroute('/');
+		}
+		if (context.url.pathname.includes('/auth/base')) {
+			return await next('/');
+		}
+	}
+	return next();
+};
+
+export const third = async (context, next) => {
+	// just making sure that we are testing the change in context coming from `next()`
+	if (context.url.pathname.startsWith('/') && contextReroute === false) {
+		context.locals.auth = 'Third function called';
+	}
+	return next();
+};
+
+export const onRequest = sequence(first, second, third);
diff --git a/packages/astro/test/fixtures/reroute/src/pages/auth/base.astro b/packages/astro/test/fixtures/reroute/src/pages/auth/base.astro
new file mode 100644
index 000000000000..be31dfb14141
--- /dev/null
+++ b/packages/astro/test/fixtures/reroute/src/pages/auth/base.astro
@@ -0,0 +1,10 @@
+---
+---
+<html>
+<head>
+	<title>Base</title>
+</head>
+<body>
+<h1>Base</h1>
+</body>
+</html>
diff --git a/packages/astro/test/fixtures/reroute/src/pages/auth/dashboard.astro b/packages/astro/test/fixtures/reroute/src/pages/auth/dashboard.astro
new file mode 100644
index 000000000000..bfa006aa01a7
--- /dev/null
+++ b/packages/astro/test/fixtures/reroute/src/pages/auth/dashboard.astro
@@ -0,0 +1,10 @@
+---
+---
+<html>
+<head>
+	<title>Dashboard</title>
+</head>
+<body>
+<h1>Dashboard</h1>
+</body>
+</html>
diff --git a/packages/astro/test/fixtures/reroute/src/pages/auth/settings.astro b/packages/astro/test/fixtures/reroute/src/pages/auth/settings.astro
new file mode 100644
index 000000000000..9eee5fe95149
--- /dev/null
+++ b/packages/astro/test/fixtures/reroute/src/pages/auth/settings.astro
@@ -0,0 +1,10 @@
+---
+---
+<html>
+<head>
+	<title>Settings</title>
+</head>
+<body>
+<h1>Settings</h1>
+</body>
+</html>
diff --git a/packages/astro/test/fixtures/reroute/src/pages/index.astro b/packages/astro/test/fixtures/reroute/src/pages/index.astro
index 727a45a65758..91a6fd0fb0fc 100644
--- a/packages/astro/test/fixtures/reroute/src/pages/index.astro
+++ b/packages/astro/test/fixtures/reroute/src/pages/index.astro
@@ -1,4 +1,5 @@
 ---
+const auth = Astro.locals.auth;
 ---
 <html>
 	<head>
@@ -6,5 +7,6 @@
 	</head>
 	<body>
 		<h1>Index</h1>
+		{auth ? <p>Called auth</p>: ""}
 	</body>
 </html>
diff --git a/packages/astro/test/reroute.test.js b/packages/astro/test/reroute.test.js
index ba0ea41bc31a..3a9273258e81 100644
--- a/packages/astro/test/reroute.test.js
+++ b/packages/astro/test/reroute.test.js
@@ -165,3 +165,36 @@ describe('SSR reroute', () => {
 		assert.equal($('h1').text(), 'Index');
 	});
 });
+
+describe('Middleware', () => {
+	/** @type {import('./test-utils').Fixture} */
+	let fixture;
+	let devServer;
+
+	before(async () => {
+		fixture = await loadFixture({
+			root: './fixtures/reroute/',
+		});
+		devServer = await fixture.startDevServer();
+	});
+
+	after(async () => {
+		await devServer.stop();
+	});
+
+	it('should render a locals populated in the third middleware function, because we use next("/")', async () => {
+		const html = await fixture.fetch('/auth/base').then((res) => res.text());
+		const $ = cheerioLoad(html);
+
+		assert.equal($('h1').text(), 'Index');
+		assert.equal($('p').text(), 'Called auth');
+	});
+
+	it('should NOT render locals populated in the third middleware function, because we use ctx.reroute("/")', async () => {
+		const html = await fixture.fetch('/auth/dashboard').then((res) => res.text());
+		const $ = cheerioLoad(html);
+
+		assert.equal($('h1').text(), 'Index');
+		assert.equal($('p').text(), '');
+	});
+});