diff --git a/src/ipc-handlers.ts b/src/ipc-handlers.ts
index eea06e0bf..9e8947fa7 100644
--- a/src/ipc-handlers.ts
+++ b/src/ipc-handlers.ts
@@ -197,6 +197,9 @@ export async function createSite(
 		blueprint?: Blueprint;
 	} = {}
 ): Promise< SiteDetails > {
+	const perfStart = performance.now();
+	console.log( '[PERF] createSite: Starting site creation' );
+
 	const { siteName, wpVersion, customDomain, enableHttps, siteId, blueprint } = config;
 
 	const forceSetupSqlite = false;
@@ -206,6 +209,7 @@ export async function createSite(
 
 	// We only recursively create the directory if the user has not selected a
 	// path from the dialog (and thus they use the "default" or suggested path).
+	const validationStart = performance.now();
 	if ( ! ( await pathExists( path ) ) && path.startsWith( DEFAULT_SITE_PATH ) ) {
 		fs.mkdirSync( path, { recursive: true } );
 	}
@@ -222,6 +226,7 @@ export async function createSite(
 	}
 
 	const port = await portFinder.getOpenPort();
+	console.log( `[PERF] createSite: Validation and port allocation took ${ ( performance.now() - validationStart ).toFixed( 2 ) }ms` );
 
 	const details = {
 		id: siteId || crypto.randomUUID(),
@@ -240,7 +245,9 @@ export async function createSite(
 
 	if ( ( await pathExists( path ) ) && ( await isEmptyDir( path ) ) ) {
 		try {
+			const setupStart = performance.now();
 			await createSiteWorkingDirectory( server, wpVersion );
+			console.log( `[PERF] createSite: WordPress setup took ${ ( performance.now() - setupStart ).toFixed( 2 ) }ms` );
 		} catch ( error ) {
 			// If site creation failed, remove the generated files and re-throw the
 			// error so it can be handled by the caller.
@@ -250,6 +257,7 @@ export async function createSite(
 	}
 
 	if ( isWordPressDirectory( path ) ) {
+		const existingWpStart = performance.now();
 		// If the directory contains a WordPress installation, and user wants to force SQLite
 		// integration, let's rename the wp-config.php file to allow WP Now to create a new one
 		// and initialize things properly.
@@ -269,11 +277,13 @@ export async function createSite(
 		} else {
 			await updateSiteUrl( server, getSiteUrl( details ) );
 		}
+		console.log( `[PERF] createSite: Existing WordPress setup took ${ ( performance.now() - existingWpStart ).toFixed( 2 ) }ms` );
 	}
 
 	const parentWindow = BrowserWindow.fromWebContents( event.sender );
 	sendIpcEventToRendererWithWindow( parentWindow, 'theme-details-updating', { id: details.id } );
 	try {
+		const saveStart = performance.now();
 		await lockAppdata();
 		userData = await loadUserData();
 
@@ -281,6 +291,8 @@ export async function createSite(
 		sortSites( userData.sites );
 
 		await saveUserData( userData );
+		console.log( `[PERF] createSite: Save user data took ${ ( performance.now() - saveStart ).toFixed( 2 ) }ms` );
+		console.log( `[PERF] createSite: Total time ${ ( performance.now() - perfStart ).toFixed( 2 ) }ms` );
 		return server.details;
 	} finally {
 		await unlockAppdata();
diff --git a/src/lib/wordpress-provider/playground-cli/playground-cli-provider.ts b/src/lib/wordpress-provider/playground-cli/playground-cli-provider.ts
index 25daafe2c..d51bdb904 100644
--- a/src/lib/wordpress-provider/playground-cli/playground-cli-provider.ts
+++ b/src/lib/wordpress-provider/playground-cli/playground-cli-provider.ts
@@ -141,11 +141,23 @@ export class PlaygroundCliProvider implements WordPressProvider {
 	}
 
 	async setupWordPressSite( server: SiteServer, wpVersion = 'latest' ): Promise< boolean > {
+		const setupStartTime = Date.now();
+		console.log( '[PERF] setupWordPressSite: Starting setup' );
+
 		const { path, name } = server.details;
 
 		try {
+			const onlineCheckStart = Date.now();
 			const isOnlineStatus = await isOnline();
+			console.log(
+				`[PERF] setupWordPressSite: Online check took ${ Date.now() - onlineCheckStart }ms`
+			);
+
+			const languageStart = Date.now();
 			const siteLanguage = await getPreferredSiteLanguage( wpVersion );
+			console.log(
+				`[PERF] setupWordPressSite: getPreferredSiteLanguage took ${ Date.now() - languageStart }ms`
+			);
 
 			const setupSteps: StepDefinition[] = [];
 
@@ -174,6 +186,9 @@ export class PlaygroundCliProvider implements WordPressProvider {
 			}
 
 			if ( ! isOnlineStatus ) {
+				console.log(
+					`[PERF] setupWordPressSite: Using bundled WordPress files (offline: ${ ! isOnlineStatus }, version: ${ wpVersion })`
+				);
 				if ( wpVersion !== 'latest' ) {
 					throw new Error(
 						`Cannot set up WordPress version '${ wpVersion }' while offline. ` +
@@ -197,7 +212,11 @@ export class PlaygroundCliProvider implements WordPressProvider {
 				}
 
 				try {
+					const copyStartTime = Date.now();
 					await recursiveCopyDirectory( bundledWPPath, path );
+					console.log(
+						`[PERF] setupWordPressSite: Copy WordPress files took ${ Date.now() - copyStartTime }ms`
+					);
 				} catch ( error ) {
 					throw new Error(
 						`Failed to copy WordPress files for offline setup: ${ ( error as Error ).message }`
@@ -211,8 +230,17 @@ export class PlaygroundCliProvider implements WordPressProvider {
 			const existingSteps = server.meta.blueprint.steps || [];
 			server.meta.blueprint.steps = [ ...setupSteps, ...existingSteps ];
 
+			const sqliteStartTime = Date.now();
 			await keepSqliteIntegrationUpdated( path );
+			console.log(
+				`[PERF] setupWordPressSite: SQLite integration update took ${
+					Date.now() - sqliteStartTime
+				}ms`
+			);
 
+			console.log(
+				`[PERF] setupWordPressSite: Total setup time ${ Date.now() - setupStartTime }ms`
+			);
 			return true;
 		} catch ( error ) {
 			console.error( 'Failed to setup WordPress site:', error );
diff --git a/src/lib/wordpress-provider/playground-cli/playground-server-process-child.ts b/src/lib/wordpress-provider/playground-cli/playground-server-process-child.ts
index f69035974..e2292cf0b 100644
--- a/src/lib/wordpress-provider/playground-cli/playground-server-process-child.ts
+++ b/src/lib/wordpress-provider/playground-cli/playground-server-process-child.ts
@@ -48,6 +48,10 @@ const originalConsoleLog = console.log;
 const originalConsoleError = console.error;
 const originalConsoleWarn = console.warn;
 
+// Track timing for playground-cli operations
+let playgroundCliStartTime: number | null = null;
+let lastLogTime: number | null = null;
+
 function formatMessageForUI( message: string ): string {
 	if ( message.includes( 'WordPress is running on' ) ) {
 		return 'WordPress is running';
@@ -59,7 +63,21 @@ function formatMessageForUI( message: string ): string {
 }
 
 console.log = ( ...args: any[] ) => {
-	originalConsoleLog( '[playground-cli]', ...args );
+	const now = Date.now();
+
+	// Initialize timing on first log
+	if ( playgroundCliStartTime === null ) {
+		playgroundCliStartTime = now;
+		lastLogTime = now;
+	}
+
+	const elapsed = now - playgroundCliStartTime;
+	const delta = lastLogTime !== null ? now - lastLogTime : 0;
+	lastLogTime = now;
+
+	// Add timing info to the log
+	originalConsoleLog( `[playground-cli | total: ${ elapsed }ms | since last: ${ delta }ms]`, ...args );
+
 	const message = args.join( ' ' );
 	process.parentPort.postMessage( { type: 'activity' } );
 	const formattedMessage = formatMessageForUI( message );
@@ -69,12 +87,30 @@ console.log = ( ...args: any[] ) => {
 };
 
 console.error = ( ...args: any[] ) => {
-	originalConsoleError( '[playground-cli]', ...args );
+	const now = Date.now();
+	if ( playgroundCliStartTime === null ) {
+		playgroundCliStartTime = now;
+		lastLogTime = now;
+	}
+	const elapsed = now - playgroundCliStartTime;
+	const delta = lastLogTime !== null ? now - lastLogTime : 0;
+	lastLogTime = now;
+
+	originalConsoleError( `[playground-cli | total: ${ elapsed }ms | since last: ${ delta }ms]`, ...args );
 	process.parentPort.postMessage( { type: 'activity' } );
 };
 
 console.warn = ( ...args: any[] ) => {
-	originalConsoleWarn( '[playground-cli]', ...args );
+	const now = Date.now();
+	if ( playgroundCliStartTime === null ) {
+		playgroundCliStartTime = now;
+		lastLogTime = now;
+	}
+	const elapsed = now - playgroundCliStartTime;
+	const delta = lastLogTime !== null ? now - lastLogTime : 0;
+	lastLogTime = now;
+
+	originalConsoleWarn( `[playground-cli | total: ${ elapsed }ms | since last: ${ delta }ms]`, ...args );
 	process.parentPort.postMessage( { type: 'activity' } );
 };
 
@@ -144,12 +180,17 @@ async function startServer(
 	options: PlaygroundCliOptions,
 	serverOptions: WordPressServerOptions
 ): Promise< void > {
+	const startServerTime = Date.now();
+	console.log( '[PERF] startServer (child): Starting server' );
+
 	if ( server ) {
 		return;
 	}
 
 	try {
+		const muPluginsStart = Date.now();
 		const [ studioMuPluginsHostPath, loaderMuPluginHostPath ] = await getMuPlugins( serverOptions );
+		console.log( `[PERF] startServer (child): getMuPlugins took ${ Date.now() - muPluginsStart }ms` );
 
 		const defaultConstants = {
 			WP_SQLITE_AST_DRIVER: true,
@@ -196,11 +237,23 @@ async function startServer(
 
 		args.blueprint.constants = { ...args.blueprint.constants, ...defaultConstants };
 
+		console.log( '[PERF] startServer (child): Calling runCLI' );
+		console.log( `[PERF] startServer (child): Blueprint has ${ args.blueprint.steps?.length || 0 } steps` );
+		const runCLIStart = Date.now();
 		server = await runCLI( args );
+		console.log( `[PERF] startServer (child): runCLI took ${ Date.now() - runCLIStart }ms` );
 
 		if ( serverOptions.adminPassword ) {
-			await setAdminPassword( server, serverOptions.adminPassword );
+			try {
+				const setPasswordStart = Date.now();
+				await setAdminPassword( server, serverOptions.adminPassword );
+				console.log( `[PERF] startServer (child): setAdminPassword took ${ Date.now() - setPasswordStart }ms` );
+			} catch {
+				console.warn( 'Failed to set admin password, but the server started successfully. Please check your site error log in wp-content/debug.log for more details' );
+			}
 		}
+
+		console.log( `[PERF] startServer (child): Total server start time ${ Date.now() - startServerTime }ms` );
 	} catch ( error ) {
 		server = null;
 		throw new Error( `Could not start server: ${ error }` );
diff --git a/src/lib/wordpress-provider/playground-cli/playground-server-process.ts b/src/lib/wordpress-provider/playground-cli/playground-server-process.ts
index ec598d350..304d628c6 100644
--- a/src/lib/wordpress-provider/playground-cli/playground-server-process.ts
+++ b/src/lib/wordpress-provider/playground-cli/playground-server-process.ts
@@ -35,7 +35,11 @@ export class PlaygroundServerProcess implements WordPressServerProcess {
 	}
 
 	async start( siteId?: string ): Promise< void > {
+		const startTime = Date.now();
+		console.log( '[PERF] PlaygroundServerProcess.start: Starting process' );
+
 		if ( this.process ) {
+			console.log( '[PERF] PlaygroundServerProcess.start: Process already running, skipping' );
 			return;
 		}
 
@@ -44,12 +48,15 @@ export class PlaygroundServerProcess implements WordPressServerProcess {
 			this.exitResolve = resolve;
 		} );
 
+		const forkStartTime = Date.now();
 		this.process = utilityProcess.fork( path.join( __dirname, 'playgroundServerProcess.js' ) );
+		console.log( `[PERF] PlaygroundServerProcess.start: Fork process took ${ Date.now() - forkStartTime }ms` );
 
 		if ( siteId ) {
 			this.siteId = siteId;
 		}
 
+		const setupListenersStart = Date.now();
 		this.process.on(
 			'message',
 			async ( message: {
@@ -117,8 +124,10 @@ export class PlaygroundServerProcess implements WordPressServerProcess {
 				this.exitResolve = null;
 			}
 		} );
+		console.log( `[PERF] PlaygroundServerProcess.start: Setup listeners took ${ Date.now() - setupListenersStart }ms` );
 
 		// Wait for child process to be ready
+		const readyWaitStart = Date.now();
 		await new Promise< void >( ( resolve ) => {
 			const readyHandler = ( message: { type?: string } ) => {
 				if ( message.type === 'ready' ) {
@@ -128,11 +137,15 @@ export class PlaygroundServerProcess implements WordPressServerProcess {
 			};
 			this.process!.on( 'message', readyHandler );
 		} );
+		console.log( `[PERF] PlaygroundServerProcess.start: Wait for ready took ${ Date.now() - readyWaitStart }ms` );
 
+		const sendMessageStart = Date.now();
 		await this.sendMessage( 'start-server', {
 			options: this.options,
 			serverOptions: this.serverOptions,
 		} );
+		console.log( `[PERF] PlaygroundServerProcess.start: Send start-server message took ${ Date.now() - sendMessageStart }ms` );
+		console.log( `[PERF] PlaygroundServerProcess.start: Total start time ${ Date.now() - startTime }ms` );
 	}
 
 	async stop(): Promise< void > {
diff --git a/src/site-server.ts b/src/site-server.ts
index 8db7152a6..ab3d5257f 100644
--- a/src/site-server.ts
+++ b/src/site-server.ts
@@ -109,12 +109,17 @@ export class SiteServer {
 	}
 
 	async start() {
+		const siteStartTime = Date.now();
+		console.log( `[PERF] SiteServer.start: Starting site '${ this.details.name }'` );
+
 		if ( this.details.running || this.server ) {
+			console.log( '[PERF] SiteServer.start: Site already running, skipping' );
 			return;
 		}
 
 		// Handle custom domain if necessary
 		if ( this.details.customDomain ) {
+			const domainSetupStart = Date.now();
 			await addDomainToHosts( this.details.customDomain, this.details.port );
 			// Generate certificates for HTTPS sites *before* the server starts
 			// This ensures the certs are ready when the proxy server needs them
@@ -123,7 +128,9 @@ export class SiteServer {
 					`Generating certificates for ${ this.details.customDomain } during server start`
 				);
 
+				const certStart = Date.now();
 				const { cert, key } = await generateSiteCertificate( this.details.customDomain );
+				console.log( `[PERF] SiteServer.start: Certificate generation took ${ Date.now() - certStart }ms` );
 				this.details = {
 					...this.details,
 					tlsKey: key,
@@ -131,9 +138,14 @@ export class SiteServer {
 				};
 			}
 			await startProxyServer();
+			console.log( `[PERF] SiteServer.start: Domain setup took ${ Date.now() - domainSetupStart }ms` );
 		}
 
+		const blueprintFilterStart = Date.now();
 		const filteredBlueprint = filterUnsupportedBlueprintFeatures( this.meta.blueprint );
+		console.log( `[PERF] SiteServer.start: Blueprint filtering took ${ Date.now() - blueprintFilterStart }ms` );
+
+		const startServerCallTime = Date.now();
 		const serverInstance = await startServer( {
 			path: this.details.path,
 			port: this.details.port,
@@ -145,23 +157,33 @@ export class SiteServer {
 			absoluteUrl: getAbsoluteUrl( this.details ),
 			blueprint: filteredBlueprint,
 		} );
+		console.log( `[PERF] SiteServer.start: startServer call took ${ Date.now() - startServerCallTime }ms` );
 
+		const portCheckStart = Date.now();
 		const isPortAvailable = await portFinder.isPortAvailable( this.details.port );
 		if ( ! isPortAvailable ) {
 			throw new Error(
 				`Port ${ this.details.port } is not available. error code: ERROR_PORT_IN_USE`
 			);
 		}
+		console.log( `[PERF] SiteServer.start: Port check took ${ Date.now() - portCheckStart }ms` );
 
 		console.log( `Starting server for '${ this.details.name }'` );
+		const createProcessStart = Date.now();
 		this.server = createServerProcess( serverInstance );
+		console.log( `[PERF] SiteServer.start: createServerProcess took ${ Date.now() - createProcessStart }ms` );
+
+		const serverProcessStart = Date.now();
 		await this.server.start( this.details.id );
+		console.log( `[PERF] SiteServer.start: server.start took ${ Date.now() - serverProcessStart }ms` );
 
 		if ( serverInstance.options.port === undefined ) {
 			throw new Error( 'Server started with no port' );
 		}
 
+		const themeDetailsStart = Date.now();
 		const themeDetails = await phpGetThemeDetails( this.server );
+		console.log( `[PERF] SiteServer.start: phpGetThemeDetails took ${ Date.now() - themeDetailsStart }ms` );
 
 		this.details = {
 			...this.details,
@@ -174,6 +196,8 @@ export class SiteServer {
 			themeDetails,
 		};
 
+		console.log( `[PERF] SiteServer.start: Total site start time ${ Date.now() - siteStartTime }ms` );
+
 		if ( this.meta.blueprint ) {
 			this.meta.blueprint = undefined;
 		}