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 1e0a23e77e..412e09a388 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 { isConfigured: isKapaAIConfigured, openWithQuery } = useKapaAI();
 
 	const helpers: PresentationHelpers = {
 		deleteSite: () => {
@@ -142,8 +144,16 @@ export function SiteErrorModal({
 						</p>
 					)}
 				</div>
-				{view.actions.length || !view.isDeveloperError ? (
+				{view.actions.length || !view.isDeveloperError || detailText ? (
 					<div className={css.errorModalFooter}>
+						{isKapaAIConfigured && !isReporting && detailText && (
+							<Button
+								variant="secondary"
+								onClick={() => openWithQuery(detailText)}
+							>
+								Troubleshoot with AI
+							</Button>
+						)}
 						{!view.isDeveloperError &&
 						!isReporting &&
 						!reportSubmitted ? (
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..3f9dc9b19f
--- /dev/null
+++ b/packages/playground/website/src/components/site-error-modal/use-kapa-ai.ts
@@ -0,0 +1,97 @@
+import { useEffect, useCallback, useState } from 'react';
+// @ts-ignore - Virtual module injected by Vite
+import { kapaWebsiteId } from 'virtual:kapa-ai-config';
+
+declare global {
+	interface Window {
+		Kapa?: {
+			open: (options?: {
+				mode?: 'ai' | 'search';
+				query?: string;
+				submit?: boolean;
+			}) => void;
+			close: () => void;
+			render: (options?: { onRender?: () => void }) => void;
+			unmount: () => void;
+		};
+	}
+}
+
+const KAPA_SCRIPT_ID = 'kapa-widget-script';
+
+export function useKapaAI() {
+	const [isLoaded, setIsLoaded] = useState(false);
+	const isConfigured = Boolean(kapaWebsiteId);
+
+	useEffect(() => {
+		if (!isConfigured) {
+			return;
+		}
+
+		// Check if script already exists
+		if (document.getElementById(KAPA_SCRIPT_ID)) {
+			if (window.Kapa) {
+				setIsLoaded(true);
+			}
+			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', kapaWebsiteId);
+		script.setAttribute('data-project-name', 'WordPress Playground');
+		script.setAttribute('data-project-color', '#3858e9');
+		script.setAttribute(
+			'data-project-logo',
+			'https://playground.wordpress.net/logo-square.png'
+		);
+		script.setAttribute('data-button-hide', 'true');
+
+		script.onload = () => {
+			const checkKapa = setInterval(() => {
+				if (window.Kapa) {
+					clearInterval(checkKapa);
+					setIsLoaded(true);
+				}
+			}, 100);
+
+			setTimeout(() => clearInterval(checkKapa), 5000);
+		};
+
+		document.body.appendChild(script);
+	}, [isConfigured]);
+
+	const openWithQuery = useCallback((query: string) => {
+		if (window.Kapa) {
+			window.Kapa.open({
+				mode: 'ai',
+				query: `Suggest a solution or troubleshooting steps for the following error: ${query}`,
+				submit: true,
+			});
+
+			// Move widget container inside screen overlay so it appears on top
+			const moveContainer = () => {
+				const container = document.getElementById(
+					'kapa-widget-container'
+				);
+				const overlay = document.querySelector(
+					'.components-modal__screen-overlay'
+				);
+				if (container && overlay) {
+					overlay.insertBefore(container, overlay.firstChild);
+				} else {
+					setTimeout(moveContainer, 50);
+				}
+			};
+			setTimeout(moveContainer, 50);
+		}
+	}, []);
+
+	return {
+		isConfigured,
+		isLoaded,
+		openWithQuery,
+	};
+}
diff --git a/packages/playground/website/vite.config.ts b/packages/playground/website/vite.config.ts
index 141daa83c8..3594143c60 100644
--- a/packages/playground/website/vite.config.ts
+++ b/packages/playground/website/vite.config.ts
@@ -105,6 +105,13 @@ export default defineConfig(({ command, mode }) => {
 				content: `
 				export const corsProxyUrl = ${JSON.stringify(corsProxyUrl || undefined)};`,
 			}),
+			virtualModule({
+				name: 'kapa-ai-config',
+				content: `
+				export const kapaWebsiteId = ${JSON.stringify(
+					process.env.KAPA_WEBSITE_ID || ''
+				)};`,
+			}),
 			// GitHub OAuth flow
 			{
 				name: 'configure-server',