diff --git a/apps/web/app/api/chat/route.ts b/apps/web/app/api/chat/route.ts
index 8e91b9c60bd..efc2f026b6e 100644
--- a/apps/web/app/api/chat/route.ts
+++ b/apps/web/app/api/chat/route.ts
@@ -44,7 +44,8 @@ export async function POST(req: Request) {
 		messages,
 		sessionId,
 		sessionKey,
-	}: { messages: UIMessage[]; sessionId?: string; sessionKey?: string } = await req.json();
+		distinctId,
+	}: { messages: UIMessage[]; sessionId?: string; sessionKey?: string; distinctId?: string } = await req.json();
 
 	const lastUserMessage = messages.filter((m) => m.role === "user").pop();
 	const userText =
@@ -60,10 +61,14 @@ export async function POST(req: Request) {
 		return new Response("No message provided", { status: 400 });
 	}
 
-	trackServer("chat_message_sent", {
-		message_length: userText.length,
-		is_subagent: typeof sessionKey === "string" && sessionKey.includes(":subagent:"),
-	});
+	trackServer(
+		"chat_message_sent",
+		{
+			message_length: userText.length,
+			is_subagent: typeof sessionKey === "string" && sessionKey.includes(":subagent:"),
+		},
+		distinctId,
+	);
 
 	const isSubagentSession = typeof sessionKey === "string" && sessionKey.includes(":subagent:");
 
diff --git a/apps/web/app/api/feedback/route.ts b/apps/web/app/api/feedback/route.ts
index 0bbf8647bf1..0ecec894542 100644
--- a/apps/web/app/api/feedback/route.ts
+++ b/apps/web/app/api/feedback/route.ts
@@ -62,12 +62,14 @@ export async function POST(req: Request) {
     }
     const conversation = lines.slice(0, cutoff);
 
-    const inputState = conversation
-      .filter((m) => m.role === "user")
-      .map((m) => ({ role: "user" as const, content: extractTextContent(m) }));
-    const outputState = conversation
-      .filter((m) => m.role === "assistant")
-      .map((m) => ({ role: "assistant" as const, content: extractTextContent(m) }));
+    const chronological = conversation.map((m) => ({
+      role: m.role as "user" | "assistant",
+      content: extractTextContent(m),
+    }));
+
+    const lastAssistant = [...conversation]
+      .reverse()
+      .find((m) => m.role === "assistant");
 
     trackServer(
       "$ai_trace",
@@ -75,8 +77,10 @@ export async function POST(req: Request) {
         $ai_trace_id: sessionId,
         $ai_session_id: sessionId,
         $ai_span_name: "chat_session",
-        $ai_input_state: inputState.length > 0 ? inputState : undefined,
-        $ai_output_state: outputState.length > 0 ? outputState : undefined,
+        $ai_input_state: chronological.length > 0 ? chronological : undefined,
+        $ai_output_state: lastAssistant
+          ? [{ role: "assistant" as const, content: extractTextContent(lastAssistant) }]
+          : undefined,
       },
       distinctId,
     );
diff --git a/apps/web/app/components/posthog-provider.tsx b/apps/web/app/components/posthog-provider.tsx
index 582d79ba7cb..c209ce1b88d 100644
--- a/apps/web/app/components/posthog-provider.tsx
+++ b/apps/web/app/components/posthog-provider.tsx
@@ -2,7 +2,7 @@
 
 import posthog from "posthog-js";
 import { PostHogProvider as PHProvider } from "posthog-js/react";
-import { useEffect } from "react";
+import { useEffect, useRef } from "react";
 import { usePathname, useSearchParams } from "next/navigation";
 
 const POSTHOG_KEY = process.env.NEXT_PUBLIC_POSTHOG_KEY || "";
@@ -10,7 +10,7 @@ const POSTHOG_HOST = "https://us.i.posthog.com";
 
 let initialized = false;
 
-function initPostHog() {
+function initPostHog(anonymousId?: string) {
   if (initialized || !POSTHOG_KEY || typeof window === "undefined") return;
 
   posthog.init(POSTHOG_KEY, {
@@ -21,6 +21,9 @@ function initPostHog() {
     autocapture: false,
     disable_session_recording: true,
     person_profiles: "identified_only",
+    bootstrap: anonymousId
+      ? { distinctID: anonymousId, isIdentifiedID: false }
+      : undefined,
   });
   initialized = true;
 }
@@ -40,12 +43,18 @@ function PageviewTracker() {
 
 export function PostHogProvider({
   children,
+  anonymousId,
 }: {
   children: React.ReactNode;
+  anonymousId?: string;
 }) {
+  const initRef = useRef(false);
+
   useEffect(() => {
-    initPostHog();
-  }, []);
+    if (initRef.current) return;
+    initRef.current = true;
+    initPostHog(anonymousId);
+  }, [anonymousId]);
 
   if (!POSTHOG_KEY) return <>{children}</>;
 
diff --git a/apps/web/app/layout.tsx b/apps/web/app/layout.tsx
index 13edae493b3..0f46760724f 100644
--- a/apps/web/app/layout.tsx
+++ b/apps/web/app/layout.tsx
@@ -1,5 +1,6 @@
 import type { Metadata, Viewport } from "next";
 import { Suspense } from "react";
+import { getOrCreateAnonymousId } from "@/lib/telemetry";
 import { PostHogProvider } from "./components/posthog-provider";
 import "./globals.css";
 
@@ -20,6 +21,8 @@ export default function RootLayout({
 }: {
   children: React.ReactNode;
 }) {
+  const anonymousId = getOrCreateAnonymousId();
+
   return (
     <html lang="en" suppressHydrationWarning>
       <head>
@@ -42,7 +45,7 @@ export default function RootLayout({
       </head>
       <body className="antialiased">
         <Suspense fallback={null}>
-          <PostHogProvider>
+          <PostHogProvider anonymousId={anonymousId}>
             {children}
           </PostHogProvider>
         </Suspense>
diff --git a/apps/web/lib/telemetry.ts b/apps/web/lib/telemetry.ts
index 8c9de8b37b4..2c4c7add8d5 100644
--- a/apps/web/lib/telemetry.ts
+++ b/apps/web/lib/telemetry.ts
@@ -1,4 +1,6 @@
 import { randomUUID } from "node:crypto";
+import { existsSync, readFileSync, writeFileSync, mkdirSync } from "node:fs";
+import { join, dirname } from "node:path";
 import { PostHog } from "posthog-node";
 
 const POSTHOG_KEY = process.env.NEXT_PUBLIC_POSTHOG_KEY || "";
@@ -18,6 +20,40 @@ function ensureClient(): PostHog | null {
   return client;
 }
 
+let _cachedAnonymousId: string | null = null;
+
+/**
+ * Read the persisted install-scoped anonymous ID from ~/.openclaw-dench/telemetry.json,
+ * generating and writing one if absent.
+ */
+export function getOrCreateAnonymousId(): string {
+  if (_cachedAnonymousId) return _cachedAnonymousId;
+
+  try {
+    const stateDir = join(process.env.HOME || "~", ".openclaw-dench");
+    const configPath = join(stateDir, "telemetry.json");
+
+    let raw: Record<string, unknown> = {};
+    if (existsSync(configPath)) {
+      raw = JSON.parse(readFileSync(configPath, "utf-8"));
+    }
+    if (typeof raw.anonymousId === "string" && raw.anonymousId) {
+      _cachedAnonymousId = raw.anonymousId;
+      return raw.anonymousId;
+    }
+    const id = randomUUID();
+    raw.anonymousId = id;
+    mkdirSync(dirname(configPath), { recursive: true });
+    writeFileSync(configPath, JSON.stringify(raw, null, 2) + "\n", "utf-8");
+    _cachedAnonymousId = id;
+    return id;
+  } catch {
+    const id = randomUUID();
+    _cachedAnonymousId = id;
+    return id;
+  }
+}
+
 export function trackServer(
   event: string,
   properties?: Record<string, unknown>,
@@ -27,7 +63,7 @@ export function trackServer(
   if (!ph) return;
 
   ph.capture({
-    distinctId: distinctId || randomUUID(),
+    distinctId: distinctId || getOrCreateAnonymousId(),
     event,
     properties: {
       ...properties,