diff --git a/packages/playground/website/vite.config.ts b/packages/playground/website/vite.config.ts
index 3be04cafef..8d67916f18 100644
--- a/packages/playground/website/vite.config.ts
+++ b/packages/playground/website/vite.config.ts
@@ -19,6 +19,7 @@ import { fileURLToPath } from 'node:url';
 import { copyFileSync, existsSync } from 'node:fs';
 import { join } from 'node:path';
 import { buildVersionPlugin } from '../../vite-extensions/vite-build-version';
+import { listAssetsRequiredForOfflineMode } from '../../vite-extensions/vite-list-assets-required-for-offline-mode';
 
 const proxy = {
 	'^/plugin-proxy': {
@@ -134,6 +135,13 @@ export default defineConfig(({ command, mode }) => {
 					}
 				},
 			} as Plugin,
+			/**
+			 * Generate a list of files needed for the website to function offline.
+			 */
+			listAssetsRequiredForOfflineMode({
+				outputFile: 'assets-required-for-offline-mode.json',
+				distDirectoriesToList: ['./', '../remote', '../client'],
+			}) as Plugin,
 		],
 
 		// Configuration for building your library.
diff --git a/packages/vite-extensions/vite-list-assets-required-for-offline-mode.ts b/packages/vite-extensions/vite-list-assets-required-for-offline-mode.ts
new file mode 100644
index 0000000000..cceff00120
--- /dev/null
+++ b/packages/vite-extensions/vite-list-assets-required-for-offline-mode.ts
@@ -0,0 +1,121 @@
+import { readdirSync, statSync, writeFileSync } from 'node:fs';
+import { join } from 'node:path';
+
+/**
+ * We want to cache all files from the website root directory, except for the files listed below.
+ */
+const patternsToNotCache = [
+	/**
+	 * Static files that are not needed for the website to function offline.
+	 */
+	'/package.json',
+	'/README.md',
+	'/.DS_Store',
+	'/index.cjs',
+	'/index.d.ts',
+	/\/lib\/.*/, // Remote lib files
+	/\/test-fixtures\/.*/, // Test fixtures
+	/**
+	 * WordPress assets removed from the minified builds, for example:
+	 *
+	 *      /wp-6.2/wp-content/themes/twentytwentyone/style.css
+	 *
+	 * We don't need to cache them, because they're only used in a short time
+	 * window after the Playground is initially loaded and before they're all backfilled
+	 * from a dedicated ZIP file shipping all the static assets for a given minified
+	 * build.
+	 *
+	 * See <Assets backfilling PR link>
+	 */
+	/^\/wp-[\w+((\.\d+)?)]+\/.*/,
+	/**
+	 * Demos are not needed for the website to function offline.
+	 */
+	/^\/demos\/.*/,
+	/**
+	 * Files needed only by the playground.wordpress.net server.
+	 */
+	'/.htaccess',
+	/**
+	 * We can't download the PHP scripts – only get their execution result. This is fine,
+	 * we don't need them for the offline mode anyway. This includes things like plugins-proxy.php.
+	 */
+	/\/.*\.php$/,
+	/**
+	 * WordPress, PHP, and SQLite files that are loaded during boot.
+	 * Eagerly loading all the PHP and WordPress releases offered by Playground would use an
+	 * extra ~200MB of bandwidth every time you load Playground on a new device.
+	 *
+	 * However, most of the time time you only want to load a specific Playground configuration.
+	 *
+	 * Therefore, in here we're excluding the PHP and WP releases from being loaded
+	 * eagerly and instead we're defaulting to caching the specific release that's
+	 * loaded anyway when booting Playgroung.
+	 */
+	/^\/assets\/php_.*\.wasm$/, // PHP WASM files
+	/^\/assets\/php_.*\.js$/, // PHP JS files
+	/^\/assets\/wp-.*\.zip$/, // Minified WordPress builds and static assets bundles
+	/^\/assets\/sqlite-database-integration-[\w]+\.zip/, // SQLite plugin
+];
+
+function listFiles(dirPath: string, fileList: string[] = []) {
+	const files = readdirSync(dirPath);
+
+	files.forEach((file) => {
+		const filePath = join(dirPath, file);
+		const fileStat = statSync(filePath);
+
+		if (fileStat.isDirectory()) {
+			listFiles(filePath, fileList);
+		} else {
+			fileList.push(filePath);
+		}
+	});
+
+	return fileList;
+}
+
+/**
+ * This Vite plugin saves a list of those files as a JSON file served on
+ * `playground.wordpress.net`. Playground then consults the list to
+ * download and cache all those files at the end of the boot process.
+ * .
+ */
+export const listAssetsRequiredForOfflineMode = ({
+	outputFile,
+	distDirectoriesToList,
+}: {
+	outputFile: string;
+	distDirectoriesToList: string[];
+}) => {
+	return {
+		name: 'list-assets-required-for-offline-mode',
+		apply: 'build',
+		writeBundle({ dir: outputDir }: { dir: string }) {
+			const files = distDirectoriesToList.flatMap((dir) => {
+				const absoluteDirPath = join(outputDir, dir);
+				console.log(`Listing files in ${absoluteDirPath}`);
+				return listFiles(absoluteDirPath)
+					.map((file) => {
+						file = file.replace(absoluteDirPath, '');
+						if (file.startsWith('/')) {
+							return file;
+						}
+						return `/${file}`;
+					})
+					.filter((item) => {
+						return !patternsToNotCache.some((pattern) => {
+							if (pattern instanceof RegExp) {
+								return pattern.test(item);
+							}
+							return pattern === item;
+						});
+					});
+			});
+			writeFileSync(
+				join(outputDir, outputFile),
+				JSON.stringify(files, null, 2)
+			);
+		},
+	};
+};