diff --git a/.changeset/witty-wasps-tie.md b/.changeset/witty-wasps-tie.md
new file mode 100644
index 000000000000..ddb7c987f715
--- /dev/null
+++ b/.changeset/witty-wasps-tie.md
@@ -0,0 +1,13 @@
+---
+'astro': patch
+---
+
+Improved the error message when a redirect can't be mapped to its destination. For example, the following redirect
+will throw a new error because `/category/[categories]/` contains one dynamic segment, while `/category/[categories]/[page]` has two dynamic segments,
+and Astro doesn't know how map the parameters:
+
+```js
+export default defineConfig({
+  redirects: { "/category/[categories]": "/category/[categories]/[page]" }
+})
+```
diff --git a/packages/astro/src/core/errors/errors-data.ts b/packages/astro/src/core/errors/errors-data.ts
index e8348355da46..eaf4937da454 100644
--- a/packages/astro/src/core/errors/errors-data.ts
+++ b/packages/astro/src/core/errors/errors-data.ts
@@ -981,6 +981,25 @@ export const UnsupportedExternalRedirect = {
 	hint: 'An external redirect must start with http or https, and must be a valid URL.',
 } satisfies ErrorData;
 
+/**
+ * @docs
+ * @see
+ * - [Astro.redirect](https://docs.astro.build/en/reference/api-reference/#redirect)
+ * @description
+ * A redirect can't be mapped when origin and destination have different segments.
+ */
+export const RedirectMappingMismatch = {
+	name: 'RedirectMappingMismatch',
+	title: "A redirect can't be mapped when origin and destination have different segments",
+	message: (
+		fromRoute: string,
+		toRoute: string,
+		fromDynamicSegments: number,
+		toDynamicSegments: number,
+	) =>
+		`The number of dynamic segments don't match. The route ${fromRoute} has ${fromDynamicSegments} segments, while ${toRoute} has ${toDynamicSegments} segments.`,
+} satisfies ErrorData;
+
 /**
  * @docs
  * @see
diff --git a/packages/astro/src/core/routing/manifest/create.ts b/packages/astro/src/core/routing/manifest/create.ts
index ad093f04b73c..8ed6120df1b9 100644
--- a/packages/astro/src/core/routing/manifest/create.ts
+++ b/packages/astro/src/core/routing/manifest/create.ts
@@ -14,6 +14,7 @@ import type { RouteData, RoutePart } from '../../../types/public/internal.js';
 import { SUPPORTED_MARKDOWN_FILE_EXTENSIONS } from '../../constants.js';
 import {
 	MissingIndexForInternationalization,
+	RedirectMappingMismatch,
 	UnsupportedExternalRedirect,
 } from '../../errors/errors-data.js';
 import { AstroError } from '../../errors/index.js';
@@ -364,6 +365,12 @@ function createRedirectRoutes(
 			});
 		}
 
+		const redirectRoute = routeMap.get(destination);
+
+		if (redirectRoute) {
+			validateRouteMapping(segments, from, redirectRoute.segments ?? [], redirectRoute.route ?? '');
+		}
+
 		routes.push({
 			type: 'redirect',
 			// For backwards compatibility, a redirect is never considered an index route.
@@ -377,7 +384,7 @@ function createRedirectRoutes(
 			pathname: pathname || void 0,
 			prerender: getPrerenderDefault(config),
 			redirect: to,
-			redirectRoute: routeMap.get(destination),
+			redirectRoute,
 			fallbackRoutes: [],
 			distURL: [],
 			origin: 'project',
@@ -387,6 +394,54 @@ function createRedirectRoutes(
 	return routes;
 }
 
+/**
+ * Checks whether `a` can be mapped to `b`. If the requirements don't match,
+ * an error is thrown.
+ * @param fromSegments
+ * @param fromRoute
+ * @param toSegments
+ * @param toRoute
+ */
+function validateRouteMapping(
+	fromSegments: RoutePart[][],
+	fromRoute: string,
+	toSegments: RoutePart[][],
+	toRoute: string,
+) {
+	const fromHasSpread = fromSegments.some((routePart) => routePart.some((part) => part.spread));
+	const toHasSpread = toSegments.some((routePart) => routePart.some((part) => part.spread));
+
+	if (fromHasSpread || toHasSpread) {
+		return;
+	}
+
+	const fromDynamicSegments = fromSegments.reduce((dynamicSegments, routePart) => {
+		if (routePart.some((part) => part.dynamic || part.spread)) {
+			dynamicSegments += 1;
+		}
+		return dynamicSegments;
+	}, 0);
+
+	const toDynamicSegments = toSegments.reduce((dynamicSegments, routePart) => {
+		if (routePart.some((part) => part.dynamic || part.spread)) {
+			dynamicSegments += 1;
+		}
+		return dynamicSegments;
+	}, 0);
+
+	if (fromDynamicSegments != toDynamicSegments) {
+		throw new AstroError({
+			...RedirectMappingMismatch,
+			message: RedirectMappingMismatch.message(
+				fromRoute,
+				toRoute,
+				fromDynamicSegments,
+				toDynamicSegments,
+			),
+		});
+	}
+}
+
 /**
  * Checks whether a route segment is static.
  */
diff --git a/packages/astro/test/fixtures/redirects/src/pages/old/[category]/[slug].astro b/packages/astro/test/fixtures/redirects/src/pages/old/[category]/[slug].astro
new file mode 100644
index 000000000000..f9162ed675b4
--- /dev/null
+++ b/packages/astro/test/fixtures/redirects/src/pages/old/[category]/[slug].astro
@@ -0,0 +1,12 @@
+---
+
+export function getStaticPaths() {
+	return [{ params: { category: 'test', slug: 'test' } }]
+}
+
+const { slug, category } = Astro.params
+---
+
+<p>
+	{slug} and {category}
+</p>
diff --git a/packages/astro/test/fixtures/redirects/src/pages/old/[category]/index.astro b/packages/astro/test/fixtures/redirects/src/pages/old/[category]/index.astro
new file mode 100644
index 000000000000..70d870acd8df
--- /dev/null
+++ b/packages/astro/test/fixtures/redirects/src/pages/old/[category]/index.astro
@@ -0,0 +1,8 @@
+---
+
+export function getStaticPaths() {
+	return [{ params: { category: 'test' } }]
+}
+---
+
+<h1>Redirect me!</h1>
diff --git a/packages/astro/test/redirects.test.js b/packages/astro/test/redirects.test.js
index 276924dfda14..bfe13245fd21 100644
--- a/packages/astro/test/redirects.test.js
+++ b/packages/astro/test/redirects.test.js
@@ -345,4 +345,26 @@ describe('Astro.redirect', () => {
 			assert.equal(secretHtml.includes('url=/login'), true);
 		});
 	});
+
+	describe('should fail for redirects that cannot be mapped ', () => {
+		it('should fail for redirects that cannot be mapped', async () => {
+			fixture = await loadFixture({
+				root: './fixtures/redirects/',
+				output: 'static',
+				redirects: {
+					'/old/[category]/1': '/old/[category]/[slug]',
+				},
+			});
+			try {
+				await fixture.build();
+				assert.fail('Expected build to fail');
+			} catch (e) {
+				assert.equal(
+					e.message,
+					"The number of dynamic segments don't match. The route /old/[category]/1 has 1 segments, while /old/[category]/[slug] has 2 segments.",
+				);
+				assert.ok(true);
+			}
+		});
+	});
 });