diff --git a/packages/playground/blueprints/src/index.ts b/packages/playground/blueprints/src/index.ts
index 579fd0b317..cdc21bcbf5 100644
--- a/packages/playground/blueprints/src/index.ts
+++ b/packages/playground/blueprints/src/index.ts
@@ -3,7 +3,11 @@ import '@php-wasm/node-polyfills';
 
 export * from './lib/steps';
 export * from './lib/steps/handlers';
-export { runBlueprintSteps, compileBlueprint } from './lib/compile';
+export {
+	runBlueprintSteps,
+	compileBlueprint,
+	isStepDefinition,
+} from './lib/compile';
 export type { Blueprint, PHPConstants } from './lib/blueprint';
 export type {
 	CompiledStep,
diff --git a/packages/playground/blueprints/src/lib/compile.ts b/packages/playground/blueprints/src/lib/compile.ts
index 932522e448..254d267dc5 100644
--- a/packages/playground/blueprints/src/lib/compile.ts
+++ b/packages/playground/blueprints/src/lib/compile.ts
@@ -405,7 +405,7 @@ function compileVersion<T>(
  * @param step The object to test
  * @returns Whether the object is a StepDefinition
  */
-function isStepDefinition(
+export function isStepDefinition(
 	step: Step | string | undefined | false | null
 ): step is StepDefinition {
 	return !!(typeof step === 'object' && step);
diff --git a/packages/playground/website/src/components/layout/index.tsx b/packages/playground/website/src/components/layout/index.tsx
index bdd9c23ef7..5f6801dbc2 100644
--- a/packages/playground/website/src/components/layout/index.tsx
+++ b/packages/playground/website/src/components/layout/index.tsx
@@ -32,6 +32,7 @@ import {
 	setActiveModal,
 	setSiteManagerOpen,
 } from '../../lib/state/redux/slice-ui';
+import { logErrorEvent } from '../../lib/tracking';
 import { ImportFormModal } from '../import-form-modal';
 import { PreviewPRModal } from '../../github/preview-pr';
 import { MissingSiteModal } from '../missing-site-modal';
@@ -164,6 +165,8 @@ function Modals(blueprint: Blueprint) {
 	useEffect(() => {
 		addCrashListener(logger, (e) => {
 			const error = e as CustomEvent;
+			logErrorEvent(error.detail.source ?? 'unknown');
+
 			if (error.detail?.source === 'php-wasm') {
 				dispatch(setActiveModal(modalSlugs.ERROR_REPORT));
 			}
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 6ae9b4664e..c043898c6b 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
@@ -10,8 +10,12 @@ import {
 	removeClientInfo,
 	updateClientInfo,
 } from './slice-clients';
-import { logTrackingEvent } from '../../tracking';
-import { Blueprint, StepDefinition } from '@wp-playground/blueprints';
+import {
+	logBlueprintEvents,
+	logErrorEvent,
+	logTrackingEvent,
+} from '../../tracking';
+import { Blueprint } from '@wp-playground/blueprints';
 import { logger } from '@php-wasm/logger';
 import { setupPostMessageRelay } from '@php-wasm/web';
 import { startPlaygroundWeb } from '@wp-playground/client';
@@ -93,26 +97,16 @@ export function bootSiteClient(
 			}
 		}
 
-		logTrackingEvent('load');
-
 		let blueprint: Blueprint;
 		if (isWordPressInstalled) {
 			blueprint = site.metadata.runtimeConfiguration;
 		} else {
 			blueprint = site.metadata.originalBlueprint;
-			// Log the names of provided Blueprint's steps.
-			// Only the names (e.g. "runPhp" or "login") are logged. Step options like
-			// code, password, URLs are never sent anywhere.
-			const steps = (blueprint?.steps || [])
-				?.filter(
-					(step: any) => !!(typeof step === 'object' && step?.step)
-				)
-				.map((step) => (step as StepDefinition).step);
-			for (const step of steps) {
-				logTrackingEvent('step', { step });
-			}
 		}
 
+		logTrackingEvent('load');
+		logBlueprintEvents(blueprint);
+
 		let playground: PlaygroundClient;
 		try {
 			playground = await startPlaygroundWeb({
@@ -177,6 +171,7 @@ export function bootSiteClient(
 			}
 		} catch (e) {
 			logger.error(e);
+			logErrorEvent('bootSiteClient');
 			dispatch(setActiveSiteError('site-boot-failed'));
 			dispatch(setActiveModal(modalSlugs.ERROR_REPORT));
 			return;
diff --git a/packages/playground/website/src/lib/tracking.ts b/packages/playground/website/src/lib/tracking.ts
index 1dbc0b85a0..4629a3d3f6 100644
--- a/packages/playground/website/src/lib/tracking.ts
+++ b/packages/playground/website/src/lib/tracking.ts
@@ -1,23 +1,113 @@
+import { Blueprint, isStepDefinition } from '@wp-playground/blueprints';
+import { logger } from '@php-wasm/logger';
+
 /**
  * Declare the global window.gtag function
  */
 declare global {
-    interface Window { gtag: any; }
+	interface Window {
+		gtag: any;
+	}
 }
 
 /**
  * Google Analytics event names
  */
-type GAEvent = 'load' | 'step';
+type GAEvent = 'load' | 'step' | 'installPlugin' | 'installTheme' | 'error';
 
 /**
  * Log a tracking event to Google Analytics
  * @param GAEvent The event name
  * @param Object Event data
  */
-export const logTrackingEvent = (event: GAEvent, data?: {[key: string]: string}) => {
-    if (typeof window === 'undefined' || !window.gtag) {
-        return;
-    }
-    window.gtag('event', event, data);
-}
+export const logTrackingEvent = (
+	event: GAEvent,
+	data?: { [key: string]: string }
+) => {
+	try {
+		if (typeof window === 'undefined' || !window.gtag) {
+			return;
+		}
+		window.gtag('event', event, data);
+	} catch (error) {
+		logger.warn('Failed to log tracking event', event, data, error);
+	}
+};
+
+/**
+ * Log error events
+ *
+ * @param error The error
+ */
+export const logErrorEvent = (source: string) => {
+	logTrackingEvent('error', {
+		source,
+	});
+};
+
+/**
+ * Log plugin install events
+ * @param slug The plugin slug
+ */
+export const logPluginInstallEvent = (slug: string) => {
+	logTrackingEvent('installPlugin', {
+		plugin: slug,
+	});
+};
+
+/**
+ * Log theme install events
+ * @param slug The theme slug
+ */
+export const logThemeInstallEvent = (slug: string) => {
+	logTrackingEvent('installTheme', {
+		theme: slug,
+	});
+};
+
+/**
+ * Log Blueprint events
+ * @param blueprint The Blueprint
+ */
+export const logBlueprintEvents = (blueprint: Blueprint) => {
+	/**
+	 * Log the names of provided Blueprint steps.
+	 * Only the names (e.g. "runPhp" or "login") are logged. Step options like
+	 * code, password, URLs are never sent anywhere.
+	 *
+	 * For installPlugin and installTheme, the plugin/theme slug is logged.
+	 */
+	if (blueprint.steps) {
+		for (const step of blueprint.steps) {
+			if (!isStepDefinition(step)) {
+				continue;
+			}
+			logTrackingEvent('step', { step: step.step });
+			if (
+				step.step === 'installPlugin' &&
+				(step as any).pluginData.slug
+			) {
+				logPluginInstallEvent((step as any).pluginData.slug);
+			} else if (
+				step.step === 'installTheme' &&
+				(step as any).themeData.slug
+			) {
+				logThemeInstallEvent((step as any).themeData.slug);
+			}
+		}
+	}
+
+	/**
+	 * Because the Blueprint isn't compiled, we need to log the plugins
+	 * that are installed using the `plugins` shorthand.
+	 */
+	if (blueprint.plugins) {
+		for (const plugin of blueprint.plugins) {
+			if (typeof plugin !== 'string') {
+				continue;
+			}
+			logTrackingEvent('step', { step: 'installPlugin' });
+			logPluginInstallEvent(plugin);
+		}
+	}
+};