diff --git a/apps/web/src/hooks/useChatSession.ts b/apps/web/src/hooks/useChatSession.ts
index 571fe7c..ab07704 100644
--- a/apps/web/src/hooks/useChatSession.ts
+++ b/apps/web/src/hooks/useChatSession.ts
@@ -1,4 +1,5 @@
-import { useCallback, useMemo, useRef } from 'react';
+import { useCallback, useMemo, useRef, useState } from 'react';
+import { toast } from 'sonner';
 import { trpc } from '@/lib/trpc';
 import { useLiveUpdates } from './useLiveUpdates';
 
@@ -46,10 +47,13 @@ export function useChatSession(
 ): UseChatSessionResult {
   const utils = trpc.useUtils();
 
+  // Optimistic messages shown before server confirms
+  const [optimisticMessages, setOptimisticMessages] = useState<ChatMessage[]>([]);
+
   // Live updates for chat + agent events
   useLiveUpdates([
     { prefix: 'chat:', invalidate: ['getChatSession'] },
-    { prefix: 'agent:', invalidate: ['getChatSession'] },
+    { prefix: 'agent:', invalidate: ['getChatSession', 'getAgent'] },
     { prefix: 'changeset:', invalidate: ['getChatSession'] },
   ]);
 
@@ -59,7 +63,14 @@ export function useChatSession(
     { enabled: !!targetId },
   );
   const session = (sessionQuery.data as ChatSession | null) ?? null;
-  const messages = session?.messages ?? [];
+  const serverMessages = session?.messages ?? [];
+
+  // Merge: show server messages, plus any optimistic ones not yet confirmed
+  const serverMsgIds = new Set(serverMessages.map(m => m.id));
+  const messages = [
+    ...serverMessages,
+    ...optimisticMessages.filter(m => !serverMsgIds.has(m.id)),
+  ];
 
   // Query agent status if session has an agent
   const agentQuery = trpc.getAgent.useQuery(
@@ -86,6 +97,13 @@ export function useChatSession(
   const sendMutation = trpc.sendChatMessage.useMutation({
     onSuccess: () => {
       void utils.getChatSession.invalidate({ targetType, targetId });
+      // Clear optimistic messages once server confirms
+      setOptimisticMessages([]);
+    },
+    onError: (err) => {
+      toast.error(`Chat failed: ${err.message}`);
+      // Remove optimistic messages on error
+      setOptimisticMessages([]);
     },
   });
 
@@ -94,6 +112,9 @@ export function useChatSession(
     onSuccess: () => {
       void utils.getChatSession.invalidate({ targetType, targetId });
     },
+    onError: (err) => {
+      toast.error(`Failed to close chat: ${err.message}`);
+    },
   });
 
   const sendMutateRef = useRef(sendMutation.mutate);
@@ -105,6 +126,17 @@ export function useChatSession(
 
   const sendMessage = useCallback(
     (message: string) => {
+      // Add optimistic user message immediately
+      const optimistic: ChatMessage = {
+        id: `opt-${Date.now()}`,
+        chatSessionId: '',
+        role: 'user',
+        content: message,
+        changeSetId: null,
+        createdAt: new Date().toISOString(),
+      };
+      setOptimisticMessages(prev => [...prev, optimistic]);
+
       sendMutateRef.current({
         targetType,
         targetId,