diff --git a/packages/playground/website/src/components/site-error-modal/site-error-modal.tsx b/packages/playground/website/src/components/site-error-modal/site-error-modal.tsx
index c0f531d05a..4bb86eb554 100644
--- a/packages/playground/website/src/components/site-error-modal/site-error-modal.tsx
+++ b/packages/playground/website/src/components/site-error-modal/site-error-modal.tsx
@@ -20,6 +20,7 @@ import type {
 } from './types';
 import { getSiteErrorView } from './get-site-error-view';
 import type { SiteInfo } from '../../lib/state/redux/slice-sites';
+import { useKapaAI } from './use-kapa-ai';
 
 export function SiteErrorModal({
 	error,
@@ -38,6 +39,7 @@ export function SiteErrorModal({
 		isSubmittingReport,
 		handleSubmitReport,
 	} = useErrorReporting(site);
+	const kapaAI = useKapaAI();
 
 	const helpers: PresentationHelpers = {
 		deleteSite: () => {
@@ -69,6 +71,9 @@ export function SiteErrorModal({
 	});
 
 	const detailText = formatErrorDetails(errorDetails);
+	const shouldShowKapaButton =
+		!isReporting && detailText && kapaAI.isEnabled();
+
 	return (
 		<Modal
 			title={
@@ -143,8 +148,18 @@ export function SiteErrorModal({
 						</p>
 					)}
 				</div>
-				{view.actions.length || !view.isDeveloperError ? (
+				{view.actions.length || !view.isDeveloperError || detailText ? (
 					<div className={css.errorModalFooter}>
+						{shouldShowKapaButton && (
+							<Button
+								variant="secondary"
+								onClick={() =>
+									kapaAI.openWithErrorMessage(detailText!)
+								}
+							>
+								Troubleshoot with AI
+							</Button>
+						)}
 						{!view.isDeveloperError &&
 						!view.hideReportButton &&
 						!isReporting &&
diff --git a/packages/playground/website/src/components/site-error-modal/use-kapa-ai.ts b/packages/playground/website/src/components/site-error-modal/use-kapa-ai.ts
new file mode 100644
index 0000000000..3211e709c2
--- /dev/null
+++ b/packages/playground/website/src/components/site-error-modal/use-kapa-ai.ts
@@ -0,0 +1,112 @@
+import { useCallback, useRef } from 'react';
+
+const KAPA_WEBSITE_ID = 'a8b85529-1773-4710-b35f-c9ebc70ffcb6';
+const KAPA_SCRIPT_ID = 'kapa-widget-script';
+
+declare global {
+	interface Window {
+		Kapa?: {
+			open: (options?: {
+				mode?: 'ai' | 'search';
+				query?: string;
+				submit?: boolean;
+			}) => void;
+			close: () => void;
+			render: (options?: { onRender?: () => void }) => void;
+			unmount: () => void;
+		};
+	}
+}
+
+function loadKapaScript(): Promise<void> {
+	return new Promise((resolve) => {
+		// Check if script already exists and loaded
+		if (document.getElementById(KAPA_SCRIPT_ID)) {
+			if (window.Kapa) {
+				resolve();
+			} else {
+				// Script exists but not loaded yet, wait for it
+				const checkKapa = setInterval(() => {
+					if (window.Kapa) {
+						clearInterval(checkKapa);
+						resolve();
+					}
+				}, 100);
+				setTimeout(() => clearInterval(checkKapa), 5000);
+			}
+			return;
+		}
+
+		const script = document.createElement('script');
+		script.id = KAPA_SCRIPT_ID;
+		script.src = 'https://widget.kapa.ai/kapa-widget.bundle.js';
+		script.async = true;
+		script.setAttribute('data-website-id', KAPA_WEBSITE_ID);
+		script.setAttribute(
+			'data-project-name',
+			'WordPress Playground AI Assistant'
+		);
+		script.setAttribute('data-project-color', '#3858e9');
+		script.setAttribute(
+			'data-project-logo',
+			'https://wordpress.github.io/wordpress-playground/img/playground-logo.svg'
+		);
+		script.setAttribute('data-button-hide', 'true');
+		script.setAttribute('data-modal-z-index', '100001');
+		script.setAttribute('data-scale-factor', '1.3');
+
+		script.onload = () => {
+			const checkKapa = setInterval(() => {
+				if (window.Kapa) {
+					clearInterval(checkKapa);
+					resolve();
+				}
+			}, 100);
+			setTimeout(() => clearInterval(checkKapa), 5000);
+		};
+
+		document.body.appendChild(script);
+	});
+}
+
+export function useKapaAI() {
+	const hasSubmittedQuery = useRef(false);
+	const isEnabled = () => {
+		return (
+			window.location.hostname === 'playground.wordpress.net' ||
+			process.env.NODE_ENV === 'development'
+		);
+	};
+
+	const openWithErrorMessage = useCallback(async (errorMessage: string) => {
+		if (!isEnabled()) {
+			return;
+		}
+
+		await loadKapaScript();
+
+		if (window.Kapa) {
+			if (hasSubmittedQuery.current) {
+				window.Kapa.open();
+			} else {
+				const urlParams = new URLSearchParams(window.location.search);
+				const hasExternalBlueprint = urlParams.has('blueprint-url');
+				const contextPrefix = hasExternalBlueprint
+					? ''
+					: `Given the URL query parameters ${window.location.search}, `;
+
+				window.Kapa.open({
+					mode: 'ai',
+					query: `${contextPrefix}Suggest a solution or troubleshooting steps for the following error: ${errorMessage}`,
+					submit: true,
+				});
+				hasSubmittedQuery.current = true;
+			}
+		}
+	}, []);
+
+	return {
+		isEnabled,
+		openWithErrorMessage,
+	};
+}
diff --git a/packages/playground/website/vite.config.ts b/packages/playground/website/vite.config.ts
index cc10eb0657..5b74e3b3cd 100644
--- a/packages/playground/website/vite.config.ts
+++ b/packages/playground/website/vite.config.ts
@@ -43,8 +43,8 @@ export default defineConfig(({ command, mode }) => {
 		'CORS_PROXY_URL' in process.env
 			? process.env.CORS_PROXY_URL
 			: mode === 'production'
-				? 'https://wordpress-playground-cors-proxy.net/?'
-				: '/cors-proxy/?';
+			? 'https://wordpress-playground-cors-proxy.net/?'
+			: '/cors-proxy/?';
 
 	return {
 		// Split traffic from this server on dev so that the iframe content and