diff --git a/apps/macos/Sources/Clawdis/Resources/WebChat/bootstrap.js b/apps/macos/Sources/Clawdis/Resources/WebChat/bootstrap.js
index bcccdd2c0..70b032db4 100644
--- a/apps/macos/Sources/Clawdis/Resources/WebChat/bootstrap.js
+++ b/apps/macos/Sources/Clawdis/Resources/WebChat/bootstrap.js
@@ -198,42 +198,67 @@ const startChat = async () => {
   mount.appendChild(panel);
   logStatus("boot: ready");
 
-  // Periodically sync messages + thinking from the session store so webchat stays
-  // in lock-step with other transports (e.g., WhatsApp or CLI).
+  // Live sync via WebSocket so other transports (WhatsApp/CLI) appear instantly.
   let lastSyncedTs = latestTimestamp(initialMessages);
-  const syncIntervalMs = 3000;
-  async function syncFromSession() {
-    if (agent.state.isStreaming) return; // avoid stomping in-flight turns
-    try {
-      const infoUrl = new URL(`./info?session=${encodeURIComponent(sessionKey)}`, window.location.href);
-      const resp = await fetch(infoUrl, { credentials: "omit" });
-      if (!resp.ok) return;
-      const info = await resp.json();
-      const messages = Array.isArray(info.initialMessages) ? info.initialMessages : [];
-      const ts = latestTimestamp(messages);
-      const thinking = typeof info.thinkingLevel === "string" ? info.thinkingLevel : "off";
+  let ws;
+  let reconnectTimer;
 
-      if (ts && ts !== lastSyncedTs) {
-        agent.replaceMessages(messages);
-        lastSyncedTs = ts;
-      }
+  const applySnapshot = (info) => {
+    const messages = Array.isArray(info?.messages) ? info.messages : [];
+    const ts = latestTimestamp(messages);
+    const thinking = typeof info?.thinkingLevel === "string" ? info.thinkingLevel : "off";
 
-      if (thinking && thinking !== agent.state.thinkingLevel) {
-        agent.setThinkingLevel(thinking);
-        if (panel?.agentInterface) {
-          panel.agentInterface.sessionThinkingLevel = thinking;
-          panel.agentInterface.pendingThinkingLevel = null;
-          if (panel.agentInterface._messageEditor) {
-            panel.agentInterface._messageEditor.thinkingLevel = thinking;
-          }
+    if (!agent.state.isStreaming && ts && ts !== lastSyncedTs) {
+      agent.replaceMessages(messages);
+      lastSyncedTs = ts;
+    }
+
+    if (thinking && thinking !== agent.state.thinkingLevel) {
+      agent.setThinkingLevel(thinking);
+      if (panel?.agentInterface) {
+        panel.agentInterface.sessionThinkingLevel = thinking;
+        panel.agentInterface.pendingThinkingLevel = null;
+        if (panel.agentInterface._messageEditor) {
+          panel.agentInterface._messageEditor.thinkingLevel = thinking;
         }
       }
-    } catch (err) {
-      console.warn("session sync failed", err);
     }
-  }
+  };
 
-  setInterval(syncFromSession, syncIntervalMs);
+  const connectSocket = () => {
+    try {
+      const wsUrl = new URL(`./socket?session=${encodeURIComponent(sessionKey)}`, window.location.href);
+      wsUrl.protocol = wsUrl.protocol.replace("http", "ws");
+      ws = new WebSocket(wsUrl);
+
+      ws.onmessage = (ev) => {
+        try {
+          const data = JSON.parse(ev.data);
+          if (data?.type === "session") applySnapshot(data);
+        } catch (err) {
+          console.warn("ws message parse failed", err);
+        }
+      };
+
+      ws.onclose = () => {
+        ws = null;
+        if (!reconnectTimer) {
+          reconnectTimer = setTimeout(() => {
+            reconnectTimer = null;
+            connectSocket();
+          }, 2000);
+        }
+      };
+
+      ws.onerror = () => {
+        ws?.close();
+      };
+    } catch (err) {
+      console.warn("ws connect failed", err);
+    }
+  };
+
+  connectSocket();
 };
 
 startChat().catch((err) => {
diff --git a/apps/macos/Sources/Clawdis/Resources/WebChat/webchat.bundle.js b/apps/macos/Sources/Clawdis/Resources/WebChat/webchat.bundle.js
index da7daf911..596ebf1fa 100644
--- a/apps/macos/Sources/Clawdis/Resources/WebChat/webchat.bundle.js
+++ b/apps/macos/Sources/Clawdis/Resources/WebChat/webchat.bundle.js
@@ -196455,36 +196455,57 @@ const startChat = async () => {
 	mount.appendChild(panel);
 	logStatus("boot: ready");
 	let lastSyncedTs = latestTimestamp(initialMessages);
-	const syncIntervalMs = 3e3;
-	async function syncFromSession() {
-		if (agent.state.isStreaming) return;
-		try {
-			const infoUrl = new URL(`./info?session=${encodeURIComponent(sessionKey)}`, window.location.href);
-			const resp = await fetch(infoUrl, { credentials: "omit" });
-			if (!resp.ok) return;
-			const info$1 = await resp.json();
-			const messages = Array.isArray(info$1.initialMessages) ? info$1.initialMessages : [];
-			const ts = latestTimestamp(messages);
-			const thinking = typeof info$1.thinkingLevel === "string" ? info$1.thinkingLevel : "off";
-			if (ts && ts !== lastSyncedTs) {
-				agent.replaceMessages(messages);
-				lastSyncedTs = ts;
-			}
-			if (thinking && thinking !== agent.state.thinkingLevel) {
-				agent.setThinkingLevel(thinking);
-				if (panel?.agentInterface) {
-					panel.agentInterface.sessionThinkingLevel = thinking;
-					panel.agentInterface.pendingThinkingLevel = null;
-					if (panel.agentInterface._messageEditor) {
-						panel.agentInterface._messageEditor.thinkingLevel = thinking;
-					}
+	let ws;
+	let reconnectTimer;
+	const applySnapshot = (info$1) => {
+		const messages = Array.isArray(info$1?.messages) ? info$1.messages : [];
+		const ts = latestTimestamp(messages);
+		const thinking = typeof info$1?.thinkingLevel === "string" ? info$1.thinkingLevel : "off";
+		if (!agent.state.isStreaming && ts && ts !== lastSyncedTs) {
+			agent.replaceMessages(messages);
+			lastSyncedTs = ts;
+		}
+		if (thinking && thinking !== agent.state.thinkingLevel) {
+			agent.setThinkingLevel(thinking);
+			if (panel?.agentInterface) {
+				panel.agentInterface.sessionThinkingLevel = thinking;
+				panel.agentInterface.pendingThinkingLevel = null;
+				if (panel.agentInterface._messageEditor) {
+					panel.agentInterface._messageEditor.thinkingLevel = thinking;
 				}
 			}
-		} catch (err) {
-			console.warn("session sync failed", err);
 		}
-	}
-	setInterval(syncFromSession, syncIntervalMs);
+	};
+	const connectSocket = () => {
+		try {
+			const wsUrl = new URL(`./socket?session=${encodeURIComponent(sessionKey)}`, window.location.href);
+			wsUrl.protocol = wsUrl.protocol.replace("http", "ws");
+			ws = new WebSocket(wsUrl);
+			ws.onmessage = (ev) => {
+				try {
+					const data = JSON.parse(ev.data);
+					if (data?.type === "session") applySnapshot(data);
+				} catch (err) {
+					console.warn("ws message parse failed", err);
+				}
+			};
+			ws.onclose = () => {
+				ws = null;
+				if (!reconnectTimer) {
+					reconnectTimer = setTimeout(() => {
+						reconnectTimer = null;
+						connectSocket();
+					}, 2e3);
+				}
+			};
+			ws.onerror = () => {
+				ws?.close();
+			};
+		} catch (err) {
+			console.warn("ws connect failed", err);
+		}
+	};
+	connectSocket();
 };
 startChat().catch((err) => {
 	const msg = err?.stack || err?.message || String(err);
diff --git a/package.json b/package.json
index 7230a486b..1ee3f7aad 100644
--- a/package.json
+++ b/package.json
@@ -45,6 +45,7 @@
     "sharp": "^0.34.5",
     "tslog": "^4.10.2",
     "undici": "^7.16.0",
+    "ws": "^8.18.0",
     "zod": "^4.1.13"
   },
   "devDependencies": {
diff --git a/src/webchat/server.ts b/src/webchat/server.ts
index d9e68c84b..d980ed314 100644
--- a/src/webchat/server.ts
+++ b/src/webchat/server.ts
@@ -5,6 +5,7 @@ import os from "node:os";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
 import sharp from "sharp";
+import { WebSocketServer, WebSocket } from "ws";
 
 import { agentCommand } from "../commands/agent.js";
 import { loadConfig } from "../config/config.js";
@@ -33,6 +34,8 @@ type AttachmentInput = {
 type RpcPayload = { role: string; content: string };
 
 let state: WebChatServerState | null = null;
+let wss: WebSocketServer | null = null;
+const wsSessions: Map<string, Set<WebSocket>> = new Map();
 
 function resolveWebRoot() {
   const here = path.dirname(fileURLToPath(import.meta.url));
@@ -93,6 +96,19 @@ function readSessionMessages(sessionId: string, storePath: string): ChatMessage[
   return messages;
 }
 
+function broadcastSession(sessionKey: string, payload: any) {
+  const conns = wsSessions.get(sessionKey);
+  if (!conns || conns.size === 0) return;
+  const msg = JSON.stringify(payload);
+  for (const ws of conns) {
+    try {
+      ws.send(msg);
+    } catch {
+      // ignore and let close handler prune
+    }
+  }
+}
+
 async function persistAttachments(
   attachments: AttachmentInput[],
   sessionId: string,
@@ -225,6 +241,33 @@ async function handleRpc(
     return { ok: false, error: String(err) };
   }
 
+  // Push latest session state to any connected webchat clients for this sessionKey.
+  try {
+    const cfg = loadConfig();
+    const sessionCfg = cfg.inbound?.reply?.session;
+    const storePath = sessionCfg?.store
+      ? resolveStorePath(sessionCfg.store)
+      : resolveStorePath(undefined);
+    const store = loadSessionStore(storePath);
+    const persistedSessionId = pickSessionId(sessionKey, store) ?? sessionId;
+    const messages = persistedSessionId
+      ? readSessionMessages(persistedSessionId, storePath)
+      : [];
+    const sessionEntry = sessionKey ? store[sessionKey] : undefined;
+    const persistedThinking = sessionEntry?.thinkingLevel;
+    broadcastSession(sessionKey, {
+      type: "session",
+      sessionKey,
+      messages,
+      thinkingLevel:
+        typeof persistedThinking === "string"
+          ? persistedThinking
+          : cfg.inbound?.reply?.thinkingDefault ?? "off",
+    });
+  } catch {
+    // best-effort; ignore broadcast errors
+  }
+
   const jsonLine = logs.find((l) => l.trim().startsWith("{"));
   if (!jsonLine) return { ok: false, error: "no agent output" };
   try {
@@ -244,6 +287,14 @@ export async function startWebChatServer(port = WEBCHAT_DEFAULT_PORT) {
   if (state) return state;
 
   const root = resolveWebRoot();
+  // Precompute session store root for file watching
+  const cfg = loadConfig();
+  const sessionCfg = cfg.inbound?.reply?.session;
+  const storePath = sessionCfg?.store
+    ? resolveStorePath(sessionCfg.store)
+    : resolveStorePath(undefined);
+  const storeDir = path.dirname(storePath);
+
   const server = http.createServer(async (req, res) => {
     if (!req.url) return notFound(res);
     if (req.socket.remoteAddress && !req.socket.remoteAddress.startsWith("127.")) {
@@ -258,11 +309,6 @@ export async function startWebChatServer(port = WEBCHAT_DEFAULT_PORT) {
 
     if (isInfo) {
       const sessionKey = url.searchParams.get("session") ?? "main";
-      const cfg = loadConfig();
-      const sessionCfg = cfg.inbound?.reply?.session;
-      const storePath = sessionCfg?.store
-        ? resolveStorePath(sessionCfg.store)
-        : resolveStorePath(undefined);
       const store = loadSessionStore(storePath);
       const sessionId = pickSessionId(sessionKey, store);
       const messages = sessionId
@@ -345,6 +391,84 @@ export async function startWebChatServer(port = WEBCHAT_DEFAULT_PORT) {
     server.listen(port, "127.0.0.1", () => resolve());
   });
 
+  // WebSocket setup for live session updates.
+  wss = new WebSocketServer({ noServer: true });
+  server.on("upgrade", (req, socket, head) => {
+    try {
+      const url = new URL(req.url ?? "", "http://127.0.0.1");
+      if (url.pathname !== "/webchat/socket" && url.pathname !== "/socket") {
+        socket.destroy();
+        return;
+      }
+      if (req.socket.remoteAddress && !req.socket.remoteAddress.startsWith("127.")) {
+        socket.destroy();
+        return;
+      }
+      const sessionKey = url.searchParams.get("session") ?? "main";
+      wss!.handleUpgrade(req, socket, head, (ws) => {
+        ws.on("close", () => {
+          const set = wsSessions.get(sessionKey);
+          if (set) {
+            set.delete(ws);
+            if (set.size === 0) wsSessions.delete(sessionKey);
+          }
+        });
+        wsSessions.set(sessionKey, (wsSessions.get(sessionKey) ?? new Set()).add(ws));
+        // Send initial snapshot
+        const store = loadSessionStore(storePath);
+        const sessionId = pickSessionId(sessionKey, store);
+        const sessionEntry = sessionKey ? store[sessionKey] : undefined;
+        const persistedThinking = sessionEntry?.thinkingLevel;
+        const messages = sessionId ? readSessionMessages(sessionId, storePath) : [];
+        ws.send(
+          JSON.stringify({
+            type: "session",
+            sessionKey,
+            messages,
+            thinkingLevel:
+              typeof persistedThinking === "string"
+                ? persistedThinking
+                : cfg.inbound?.reply?.thinkingDefault ?? "off",
+          }),
+        );
+      });
+    } catch (err) {
+      socket.destroy();
+    }
+  });
+
+  // Watch for session/message file changes and push updates.
+  try {
+    if (fs.existsSync(storeDir)) {
+      fs.watch(storeDir, { persistent: false }, (event, filename) => {
+        if (!filename) return;
+        // On any file change, refresh for active sessions.
+        for (const sessionKey of wsSessions.keys()) {
+          try {
+            const store = loadSessionStore(storePath);
+            const sessionId = pickSessionId(sessionKey, store);
+            const sessionEntry = sessionKey ? store[sessionKey] : undefined;
+            const persistedThinking = sessionEntry?.thinkingLevel;
+            const messages = sessionId ? readSessionMessages(sessionId, storePath) : [];
+            broadcastSession(sessionKey, {
+              type: "session",
+              sessionKey,
+              messages,
+              thinkingLevel:
+                typeof persistedThinking === "string"
+                  ? persistedThinking
+                  : cfg.inbound?.reply?.thinkingDefault ?? "off",
+            });
+          } catch {
+            // ignore
+          }
+        }
+      });
+    }
+  } catch {
+    // watcher is best-effort
+  }
+
   state = { server, port };
   logDebug(`webchat server listening on 127.0.0.1:${port}`);
   return state;