diff --git a/packages/playground/blueprints/src/lib/steps/activate-plugin.spec.ts b/packages/playground/blueprints/src/lib/steps/activate-plugin.spec.ts
index 7fbf2ff4cc..44540f01f0 100644
--- a/packages/playground/blueprints/src/lib/steps/activate-plugin.spec.ts
+++ b/packages/playground/blueprints/src/lib/steps/activate-plugin.spec.ts
@@ -28,7 +28,7 @@ describe('Blueprint step activatePlugin()', () => {
 			`<?php /**\n * Plugin Name: Test Plugin */`
 		);
 		await activatePlugin(php, {
-			pluginPath: docroot + '/wp-content/plugins/test-plugin.php',
+			pluginPath: 'test-plugin.php',
 		});
 
 		const response = await php.run({
@@ -41,6 +41,24 @@ describe('Blueprint step activatePlugin()', () => {
 		expect(response.text).toBe('true');
 	});
 
+	it('should detect a silent failure in activating the plugin', async () => {
+		const docroot = php.documentRoot;
+		php.writeFile(
+			`/${docroot}/wp-content/plugins/test-plugin.php`,
+			`<?php /**\n * Plugin Name: Test Plugin */`
+		);
+		php.writeFile(
+			`/${docroot}/wp-content/mu-plugins/0-exit.php`,
+			`<?php exit(0); `
+		);
+		expect(
+			async () =>
+				await activatePlugin(php, {
+					pluginPath: 'test-plugin.php',
+				})
+		).rejects.toThrow(/Plugin test-plugin.php could not be activated/);
+	});
+
 	it('should run the activation hooks as a priviliged user', async () => {
 		const docroot = php.documentRoot;
 		const createdFilePath =
@@ -56,7 +74,7 @@ describe('Blueprint step activatePlugin()', () => {
 			`
 		);
 		await activatePlugin(php, {
-			pluginPath: docroot + '/wp-content/plugins/test-plugin.php',
+			pluginPath: 'test-plugin.php',
 		});
 
 		expect(php.fileExists(createdFilePath)).toBe(true);
diff --git a/packages/playground/blueprints/src/lib/steps/activate-plugin.ts b/packages/playground/blueprints/src/lib/steps/activate-plugin.ts
index 37a56755cb..a14b34664f 100644
--- a/packages/playground/blueprints/src/lib/steps/activate-plugin.ts
+++ b/packages/playground/blueprints/src/lib/steps/activate-plugin.ts
@@ -1,5 +1,6 @@
 import { phpVar } from '@php-wasm/util';
 import { StepHandler } from '.';
+import { logger } from '@php-wasm/logger';
 
 /**
  * @inheritDoc activatePlugin
@@ -34,7 +35,7 @@ export const activatePlugin: StepHandler<ActivatePluginStep> = async (
 	progress?.tracker.setCaption(`Activating ${pluginName || pluginPath}`);
 
 	const docroot = await playground.documentRoot;
-	await playground.run({
+	const result = await playground.run({
 		code: `<?php
 			define( 'WP_ADMIN', true );
 			require_once( ${phpVar(docroot)}. "/wp-load.php" );
@@ -69,4 +70,13 @@ export const activatePlugin: StepHandler<ActivatePluginStep> = async (
 			throw new Exception( 'Unable to activate plugin' );
 		`,
 	});
+	if (result.text !== 'Plugin activated successfully') {
+		logger.debug(result);
+		throw new Error(
+			`Plugin ${pluginPath} could not be activated – WordPress exited with no error. ` +
+				`Sometimes, when $_SERVER or site options are not configured correctly, ` +
+				`WordPress exits early with a 301 redirect. ` +
+				`Inspect the "debug" logs in the console for more details`
+		);
+	}
 };
diff --git a/packages/playground/blueprints/src/lib/steps/activate-theme.spec.ts b/packages/playground/blueprints/src/lib/steps/activate-theme.spec.ts
index 5ce4f05110..a5d99baf62 100644
--- a/packages/playground/blueprints/src/lib/steps/activate-theme.spec.ts
+++ b/packages/playground/blueprints/src/lib/steps/activate-theme.spec.ts
@@ -80,4 +80,28 @@ describe('Blueprint step activateTheme()', () => {
 
 		expect(php.fileExists(createdFilePath)).toBe(true);
 	});
+
+	it('should detect a silent failure in activating the theme', async () => {
+		const docroot = php.documentRoot;
+		php.mkdir(`${docroot}/wp-content/themes/test-theme`);
+		php.writeFile(
+			`${docroot}/wp-content/themes/test-theme/style.css`,
+			`/**
+* Theme Name: Test Theme
+* Theme URI: https://example.com/test-theme
+* Author: Test Author
+*/
+			`
+		);
+		php.writeFile(
+			`/${docroot}/wp-content/mu-plugins/0-exit.php`,
+			`<?php exit(0); `
+		);
+		expect(
+			async () =>
+				await activateTheme(php, {
+					themeFolderName: 'test-theme',
+				})
+		).rejects.toThrow(/Theme test-theme could not be activated/);
+	});
 });
diff --git a/packages/playground/blueprints/src/lib/steps/activate-theme.ts b/packages/playground/blueprints/src/lib/steps/activate-theme.ts
index 697d27bb4f..8b05fb1165 100644
--- a/packages/playground/blueprints/src/lib/steps/activate-theme.ts
+++ b/packages/playground/blueprints/src/lib/steps/activate-theme.ts
@@ -1,5 +1,5 @@
-import { phpVar } from '@php-wasm/util';
 import { StepHandler } from '.';
+import { logger } from '@php-wasm/logger';
 
 /**
  * @inheritDoc activateTheme
@@ -44,15 +44,33 @@ export const activateTheme: StepHandler<ActivateThemeStep> = async (
 			More info can be found in the Blueprint documentation: https://wordpress.github.io/wordpress-playground/blueprints-api/steps/#ActivateThemeStep
 		`);
 	}
-	await playground.run({
+	const result = await playground.run({
 		code: `<?php
 			define( 'WP_ADMIN', true );
-			require_once( ${phpVar(docroot)}. "/wp-load.php" );
+			require_once( getenv('docroot') . "/wp-load.php" );
 
 			// Set current user to admin
 			wp_set_current_user( get_users(array('role' => 'Administrator') )[0]->ID );
 
-			switch_theme( ${phpVar(themeFolderName)} );
+			switch_theme( getenv('themeFolderName') );
+
+			if( wp_get_theme()->get_stylesheet() !== getenv('themeFolderName') ) {
+				throw new Exception( 'Theme ' . getenv('themeFolderName') . ' could not be activated.' );				
+			}
+			die('Theme activated successfully');
 		`,
+		env: {
+			docroot,
+			themeFolderName,
+		},
 	});
+	if (result.text !== 'Theme activated successfully') {
+		logger.debug(result);
+		throw new Error(
+			`Theme ${themeFolderName} could not be activated – WordPress exited with no error. ` +
+				`Sometimes, when $_SERVER or site options are not configured correctly, ` +
+				`WordPress exits early with a 301 redirect. ` +
+				`Inspect the "debug" logs in the console for more details`
+		);
+	}
 };