diff --git a/.changeset/moody-points-reflect.md b/.changeset/moody-points-reflect.md
new file mode 100644
index 000000000000..44b16a18f30a
--- /dev/null
+++ b/.changeset/moody-points-reflect.md
@@ -0,0 +1,5 @@
+---
+'astro': patch
+---
+
+Correctly generate directories for assets when users customise the output via rollup options.
diff --git a/packages/astro/src/core/build/static-build.ts b/packages/astro/src/core/build/static-build.ts
index cb11a5fa06f2..b99890b829bb 100644
--- a/packages/astro/src/core/build/static-build.ts
+++ b/packages/astro/src/core/build/static-build.ts
@@ -3,6 +3,7 @@ import * as eslexer from 'es-module-lexer';
 import glob from 'fast-glob';
 import fs from 'fs';
 import { bgGreen, bgMagenta, black, dim } from 'kleur/colors';
+import path from 'path';
 import { fileURLToPath } from 'url';
 import * as vite from 'vite';
 import {
@@ -384,12 +385,15 @@ async function ssrMoveAssets(opts: StaticBuildOptions) {
 	});
 
 	if (files.length > 0) {
-		// Make the directory
-		await fs.promises.mkdir(clientAssets, { recursive: true });
+	
 		await Promise.all(
 			files.map(async (filename) => {
 				const currentUrl = new URL(filename, appendForwardSlash(serverAssets.toString()));
 				const clientUrl = new URL(filename, appendForwardSlash(clientAssets.toString()));
+				const dir = new URL(path.parse(clientUrl.href).dir)				
+				// It can't find this file because the user defines a custom path 
+				// that includes the folder paths in `assetFileNames
+				if(!fs.existsSync(dir)) await fs.promises.mkdir(dir, { recursive: true });
 				return fs.promises.rename(currentUrl, clientUrl);
 			})
 		);
diff --git a/packages/astro/test/custom-assets-name.test.js b/packages/astro/test/custom-assets-name.test.js
new file mode 100644
index 000000000000..345a9d2a7eee
--- /dev/null
+++ b/packages/astro/test/custom-assets-name.test.js
@@ -0,0 +1,21 @@
+import { expect } from 'chai';
+import { loadFixture } from './test-utils.js';
+
+describe('custom the assets name function', () => {
+	/** @type {import('./test-utils').Fixture} */
+	let fixture;
+
+	before(async () => {
+		fixture = await loadFixture({
+			root: './fixtures/custom-assets-name/',
+			output: 'server',
+		});
+		await fixture.build();
+	});
+
+	it('It cant find this file cause the node throws an error if the users custom a path that includes the folder path', async () => {
+		const csslength = await fixture.readFile('client/assets/css/a.css')
+		/** @type {Set<string>} */
+		expect(!!csslength).to.equal(true);
+	});
+});
diff --git a/packages/astro/test/fixtures/custom-assets-name/astro.config.mjs b/packages/astro/test/fixtures/custom-assets-name/astro.config.mjs
new file mode 100644
index 000000000000..c4a75e4ebc81
--- /dev/null
+++ b/packages/astro/test/fixtures/custom-assets-name/astro.config.mjs
@@ -0,0 +1,34 @@
+import { defineConfig } from 'astro/config';
+import path from "path";
+
+// https://astro.build/config
+import node from "@astrojs/node";
+
+// https://astro.build/config
+export default defineConfig({
+  vite: {
+    build: {
+      cssCodeSplit: false,
+      assetsInlineLimit: 0,
+      rollupOptions: {
+        output: {
+          
+          entryFileNames: 'assets/script/a.[hash].js',
+          assetFileNames: (option) => {
+            const { ext, dir, base } = path.parse(option.name);
+
+            if (ext == ".css") return path.join(dir, "assets/css", 'a.css');
+            return "assets/img/[name].[ext]";
+          }
+        }
+      }
+    }
+  },
+  build: {
+    assets: 'assets'
+  },
+  output: "server",
+  adapter: node({
+    mode: "standalone"
+  })
+});
diff --git a/packages/astro/test/fixtures/custom-assets-name/package.json b/packages/astro/test/fixtures/custom-assets-name/package.json
new file mode 100644
index 000000000000..00237fbddfdc
--- /dev/null
+++ b/packages/astro/test/fixtures/custom-assets-name/package.json
@@ -0,0 +1,9 @@
+{
+  "name": "@test/custom-assets-name",
+  "version": "0.0.0",
+  "private": true,
+  "dependencies": {
+    "astro": "workspace:*",
+    "@astrojs/node": "workspace:*"
+  }
+}
diff --git a/packages/astro/test/fixtures/custom-assets-name/src/pages/index.astro b/packages/astro/test/fixtures/custom-assets-name/src/pages/index.astro
new file mode 100644
index 000000000000..250233e1e15f
--- /dev/null
+++ b/packages/astro/test/fixtures/custom-assets-name/src/pages/index.astro
@@ -0,0 +1,18 @@
+---
+const title = 'My App';
+---
+
+<html>
+<head>
+  <title>{title}</title>
+</head>
+<body>
+  <h1>{title}</h1>
+</body>
+</html>
+
+<style>
+	h1 {
+		color: red;
+	}
+</style>
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 5789d3ae190a..f830bbe27278 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -1971,6 +1971,14 @@ importers:
     dependencies:
       astro: link:../../..
 
+  packages/astro/test/fixtures/custom-assets-name:
+    specifiers:
+      '@astrojs/node': workspace:*
+      astro: workspace:*
+    dependencies:
+      '@astrojs/node': link:../../../../integrations/node
+      astro: link:../../..
+
   packages/astro/test/fixtures/custom-elements:
     specifiers:
       '@test/custom-element-renderer': workspace:*