diff --git a/.changeset/proud-games-repair.md b/.changeset/proud-games-repair.md
new file mode 100644
index 0000000000..8c342e2a39
--- /dev/null
+++ b/.changeset/proud-games-repair.md
@@ -0,0 +1,7 @@
+---
+'astro': patch
+---
+
+Adds an error when `Astro.rewrite()` is used to rewrite an on-demand route with a static route when using the `"server"` output.
+
+This is a forbidden rewrite because Astro can't retrieve the emitted static route at runtime. This route is served by the hosting platform, and not Astro itself. 
diff --git a/packages/astro/src/core/errors/errors-data.ts b/packages/astro/src/core/errors/errors-data.ts
index 6b3c7c141a..7c5479a665 100644
--- a/packages/astro/src/core/errors/errors-data.ts
+++ b/packages/astro/src/core/errors/errors-data.ts
@@ -1260,6 +1260,23 @@ export const RewriteWithBodyUsed = {
 		'Astro.rewrite() cannot be used if the request body has already been read. If you need to read the body, first clone the request.',
 } satisfies ErrorData;
 
+/**
+ * @docs
+ * @description
+ * `Astro.rewrite()` can't be used to rewrite an on-demand route with a static route when using the `"server"` output.
+ *
+ */
+export const ForbiddenRewrite = {
+	name: 'ForbiddenRewrite',
+	title: 'Forbidden rewrite to a static route.',
+	message: (from: string, to: string, component: string) =>
+		`You tried to rewrite the on-demand route '${from}' with the static route '${to}', when using the 'server' output. \n\nThe static route '${to}' is rendered by the component
+'${component}', which is marked as prerendered. This is a forbidden operation because during the build the component '${component}' is compiled to an
+HTML file, which can't be retrieved at runtime by Astro.`,
+	hint: (component: string) =>
+		`Add \`export const prerender = false\` to the component '${component}', or use a Astro.redirect().`,
+} satisfies ErrorData;
+
 /**
  * @docs
  * @description
diff --git a/packages/astro/src/core/middleware/sequence.ts b/packages/astro/src/core/middleware/sequence.ts
index 1fbba7c660..99d506695e 100644
--- a/packages/astro/src/core/middleware/sequence.ts
+++ b/packages/astro/src/core/middleware/sequence.ts
@@ -1,6 +1,8 @@
 import type { MiddlewareHandler, RewritePayload } from '../../types/public/common.js';
 import type { APIContext } from '../../types/public/context.js';
 import { AstroCookies } from '../cookies/cookies.js';
+import { ForbiddenRewrite } from '../errors/errors-data.js';
+import { AstroError } from '../errors/index.js';
 import { apiContextRoutesSymbol } from '../render-context.js';
 import { type Pipeline, getParams } from '../render/index.js';
 import { defineMiddleware } from './index.js';
@@ -49,6 +51,22 @@ export function sequence(...handlers: MiddlewareHandler[]): MiddlewareHandler {
 							payload,
 							handleContext.request,
 						);
+
+						// This is a case where the user tries to rewrite from a SSR route to a prerendered route (SSG).
+						// This case isn't valid because when building for SSR, the prerendered route disappears from the server output because it becomes an HTML file,
+						// so Astro can't retrieve it from the emitted manifest.
+						if (
+							pipeline.serverLike === true &&
+							handleContext.isPrerendered === false &&
+							routeData.prerender === true
+						) {
+							throw new AstroError({
+								...ForbiddenRewrite,
+								message: ForbiddenRewrite.message(pathname, pathname, routeData.component),
+								hint: ForbiddenRewrite.hint(routeData.component),
+							});
+						}
+
 						carriedPayload = payload;
 						handleContext.request = newRequest;
 						handleContext.url = new URL(newRequest.url);
diff --git a/packages/astro/src/core/render-context.ts b/packages/astro/src/core/render-context.ts
index 49f174c33f..691613412e 100644
--- a/packages/astro/src/core/render-context.ts
+++ b/packages/astro/src/core/render-context.ts
@@ -23,6 +23,7 @@ import {
 } from './constants.js';
 import { AstroCookies, attachCookiesToResponse } from './cookies/index.js';
 import { getCookiesFromResponse } from './cookies/response.js';
+import { ForbiddenRewrite } from './errors/errors-data.js';
 import { AstroError, AstroErrorData } from './errors/index.js';
 import { callMiddleware } from './middleware/callMiddleware.js';
 import { sequence } from './middleware/index.js';
@@ -145,6 +146,22 @@ export class RenderContext {
 					pathname,
 					newUrl,
 				} = await pipeline.tryRewrite(payload, this.request);
+
+				// This is a case where the user tries to rewrite from a SSR route to a prerendered route (SSG).
+				// This case isn't valid because when building for SSR, the prerendered route disappears from the server output because it becomes an HTML file,
+				// so Astro can't retrieve it from the emitted manifest.
+				if (
+					this.pipeline.serverLike === true &&
+					this.routeData.prerender === false &&
+					routeData.prerender === true
+				) {
+					throw new AstroError({
+						...ForbiddenRewrite,
+						message: ForbiddenRewrite.message(this.pathname, pathname, routeData.component),
+						hint: ForbiddenRewrite.hint(routeData.component),
+					});
+				}
+
 				this.routeData = routeData;
 				componentInstance = newComponent;
 				if (payload instanceof Request) {
@@ -246,6 +263,21 @@ export class RenderContext {
 			reroutePayload,
 			this.request,
 		);
+		// This is a case where the user tries to rewrite from a SSR route to a prerendered route (SSG).
+		// This case isn't valid because when building for SSR, the prerendered route disappears from the server output because it becomes an HTML file,
+		// so Astro can't retrieve it from the emitted manifest.
+		if (
+			this.pipeline.serverLike === true &&
+			this.routeData.prerender === false &&
+			routeData.prerender === true
+		) {
+			throw new AstroError({
+				...ForbiddenRewrite,
+				message: ForbiddenRewrite.message(this.pathname, pathname, routeData.component),
+				hint: ForbiddenRewrite.hint(routeData.component),
+			});
+		}
+
 		this.routeData = routeData;
 		if (reroutePayload instanceof Request) {
 			this.request = reroutePayload;
diff --git a/packages/astro/test/fixtures/rewrite-server/src/pages/forbidden/dynamic.astro b/packages/astro/test/fixtures/rewrite-server/src/pages/forbidden/dynamic.astro
new file mode 100644
index 0000000000..3c23c95391
--- /dev/null
+++ b/packages/astro/test/fixtures/rewrite-server/src/pages/forbidden/dynamic.astro
@@ -0,0 +1,4 @@
+---
+return Astro.rewrite("/forbidden/static")
+export const prerender = false
+---
diff --git a/packages/astro/test/fixtures/rewrite-server/src/pages/forbidden/static.astro b/packages/astro/test/fixtures/rewrite-server/src/pages/forbidden/static.astro
new file mode 100644
index 0000000000..3a91bda712
--- /dev/null
+++ b/packages/astro/test/fixtures/rewrite-server/src/pages/forbidden/static.astro
@@ -0,0 +1,3 @@
+---
+export const prerender = true
+---
diff --git a/packages/astro/test/rewrite.test.js b/packages/astro/test/rewrite.test.js
index 273e11d073..cc75080810 100644
--- a/packages/astro/test/rewrite.test.js
+++ b/packages/astro/test/rewrite.test.js
@@ -149,6 +149,13 @@ describe('Dev rewrite, hybrid/server', () => {
 
 		assert.equal($('title').text(), 'RewriteWithBodyUsed');
 	});
+
+	it('should error when rewriting from a SSR route to a SSG route', async () => {
+		const html = await fixture.fetch('/forbidden/dynamic').then((res) => res.text());
+		const $ = cheerioLoad(html);
+
+		assert.match($('title').text(), /ForbiddenRewrite/);
+	});
 });
 
 describe('Build reroute', () => {