diff --git a/packages/playground/client/src/index.ts b/packages/playground/client/src/index.ts
index 26b2de4b3c..896ca01989 100644
--- a/packages/playground/client/src/index.ts
+++ b/packages/playground/client/src/index.ts
@@ -67,7 +67,11 @@ export interface StartPlaygroundOptions {
 	 */
 	onBeforeBlueprint?: () => Promise<void>;
 	mounts?: Array<MountDescriptor>;
-	shouldInstallWordPress?: boolean;
+	/**
+	 * Whether to install WordPress. Value may be boolean or 'auto'.
+	 * If 'auto', WordPress will be installed if it is not already installed.
+	 */
+	shouldInstallWordPress?: boolean | 'auto';
 }
 
 /**
diff --git a/packages/playground/remote/src/lib/index.ts b/packages/playground/remote/src/lib/index.ts
index 518d8848a8..2f71323d63 100644
--- a/packages/playground/remote/src/lib/index.ts
+++ b/packages/playground/remote/src/lib/index.ts
@@ -1,5 +1,6 @@
 export * from './boot-playground-remote';
 export * from './playground-client';
+export { looksLikePlaygroundDirectory } from './worker-utils';
 export {
 	MinifiedWordPressVersions,
 	MinifiedWordPressVersionsList,
diff --git a/packages/playground/remote/src/lib/worker-thread.ts b/packages/playground/remote/src/lib/worker-thread.ts
index d5100dd27a..574c588569 100644
--- a/packages/playground/remote/src/lib/worker-thread.ts
+++ b/packages/playground/remote/src/lib/worker-thread.ts
@@ -21,6 +21,7 @@ import {
 	spawnHandlerFactory,
 	backfillStaticFilesRemovedFromMinifiedBuild,
 	hasCachedStaticFilesRemovedFromMinifiedBuild,
+	looksLikePlaygroundDirectory,
 } from './worker-utils';
 import { EmscriptenDownloadMonitor } from '@php-wasm/progress';
 import { createMemoizedFetch } from './create-memoized-fetch';
@@ -72,7 +73,7 @@ export type WorkerBootOptions = {
 	scope: string;
 	withNetworking: boolean;
 	mounts?: Array<MountDescriptor>;
-	shouldInstallWordPress?: boolean;
+	shouldInstallWordPress?: boolean | 'auto';
 };
 
 /** @inheritDoc PHPClient */
@@ -188,6 +189,24 @@ export class PlaygroundWorkerEndpoint extends PHPWorker {
 		}
 
 		try {
+			if (shouldInstallWordPress === 'auto') {
+				// Default to installing WordPress unless we detect
+				// it in one of the mounts.
+				shouldInstallWordPress = true;
+
+				// NOTE: This check is insufficient if a complete WordPress
+				// installation is composed of multiple mounts.
+				for (const mount of mounts) {
+					const dirHandle = await directoryHandleFromMountDevice(
+						mount.device
+					);
+					if (await looksLikePlaygroundDirectory(dirHandle)) {
+						shouldInstallWordPress = false;
+						break;
+					}
+				}
+			}
+
 			// Start downloading WordPress if needed
 			let wordPressRequest = null;
 			if (shouldInstallWordPress) {
diff --git a/packages/playground/remote/src/lib/worker-utils.ts b/packages/playground/remote/src/lib/worker-utils.ts
index 711d8ed931..ed37e106fe 100644
--- a/packages/playground/remote/src/lib/worker-utils.ts
+++ b/packages/playground/remote/src/lib/worker-utils.ts
@@ -243,3 +243,47 @@ export async function getWordPressStaticZipUrl(php: PHP) {
 	}
 	return joinPaths('/', staticAssetsDirectory, 'wordpress-static.zip');
 }
+
+/**
+ * Check if the given directory handle directory is a Playground directory.
+ *
+ * @TODO: Create a shared package like @wp-playground/wordpress for such utilities
+ * and bring in the context detection logic from wp-now – only express it in terms of
+ * either abstract FS operations or isomorphic PHP FS operations.
+ * (we can't just use Node.js require('fs') in the browser, for example)
+ *
+ * @TODO: Reuse the "isWordPressInstalled" logic implemented in the boot protocol.
+ *        Perhaps mount OPFS first, and only then check for the presence of the
+ *        WordPress installation? Or, if not, perhaps implement a shared file access
+ * 		  abstraction that can be used both with the PHP module and OPFS directory handles?
+ *
+ * @param dirHandle
+ */
+export async function looksLikePlaygroundDirectory(
+	dirHandle: FileSystemDirectoryHandle
+) {
+	// Run this loop just to trigger an exception if the directory handle is no good.
+	// eslint-disable-next-line @typescript-eslint/no-unused-vars
+	for await (const _ of dirHandle.keys()) {
+		break;
+	}
+
+	try {
+		/**
+		 * Assume it's a Playground directory if these files exist:
+		 * - wp-config.php
+		 * - wp-content/database/.ht.sqlite
+		 */
+		await dirHandle.getFileHandle('wp-config.php', { create: false });
+		const wpContent = await dirHandle.getDirectoryHandle('wp-content', {
+			create: false,
+		});
+		const database = await wpContent.getDirectoryHandle('database', {
+			create: false,
+		});
+		await database.getFileHandle('.ht.sqlite', { create: false });
+	} catch (e) {
+		return false;
+	}
+	return true;
+}
diff --git a/packages/playground/website/src/lib/state/redux/boot-site-client.ts b/packages/playground/website/src/lib/state/redux/boot-site-client.ts
index aabb8c3bbc..476a13ce8b 100644
--- a/packages/playground/website/src/lib/state/redux/boot-site-client.ts
+++ b/packages/playground/website/src/lib/state/redux/boot-site-client.ts
@@ -15,7 +15,10 @@ import { Blueprint, StepDefinition } from '@wp-playground/blueprints';
 import { logger } from '@php-wasm/logger';
 import { setupPostMessageRelay } from '@php-wasm/web';
 import { startPlaygroundWeb } from '@wp-playground/client';
-import { PlaygroundClient } from '@wp-playground/remote';
+import {
+	PlaygroundClient,
+	looksLikePlaygroundDirectory,
+} from '@wp-playground/remote';
 import { getRemoteUrl } from '../../config';
 import { setActiveModal, setActiveSiteError } from './slice-ui';
 import { PlaygroundDispatch, PlaygroundReduxState } from './store';
@@ -72,7 +75,7 @@ export function bootSiteClient(
 		let isWordPressInstalled = false;
 		if (mountDescriptor) {
 			try {
-				isWordPressInstalled = await playgroundAvailableInOpfs(
+				isWordPressInstalled = await looksLikePlaygroundDirectory(
 					await directoryHandleFromMountDevice(mountDescriptor.device)
 				);
 			} catch (e) {
@@ -206,47 +209,3 @@ export function bootSiteClient(
 		signal.onabort = null;
 	};
 }
-
-/**
- * Check if the given directory handle directory is a Playground directory.
- *
- * @TODO: Create a shared package like @wp-playground/wordpress for such utilities
- * and bring in the context detection logic from wp-now – only express it in terms of
- * either abstract FS operations or isomorphic PHP FS operations.
- * (we can't just use Node.js require('fs') in the browser, for example)
- *
- * @TODO: Reuse the "isWordPressInstalled" logic implemented in the boot protocol.
- *        Perhaps mount OPFS first, and only then check for the presence of the
- *        WordPress installation? Or, if not, perhaps implement a shared file access
- * 		  abstraction that can be used both with the PHP module and OPFS directory handles?
- *
- * @param dirHandle
- */
-export async function playgroundAvailableInOpfs(
-	dirHandle: FileSystemDirectoryHandle
-) {
-	// Run this loop just to trigger an exception if the directory handle is no good.
-	// eslint-disable-next-line @typescript-eslint/no-unused-vars
-	for await (const _ of dirHandle.keys()) {
-		break;
-	}
-
-	try {
-		/**
-		 * Assume it's a Playground directory if these files exist:
-		 * - wp-config.php
-		 * - wp-content/database/.ht.sqlite
-		 */
-		await dirHandle.getFileHandle('wp-config.php', { create: false });
-		const wpContent = await dirHandle.getDirectoryHandle('wp-content', {
-			create: false,
-		});
-		const database = await wpContent.getDirectoryHandle('database', {
-			create: false,
-		});
-		await database.getFileHandle('.ht.sqlite', { create: false });
-	} catch (e) {
-		return false;
-	}
-	return true;
-}