diff --git a/crates/goose-server/src/routes/agent.rs b/crates/goose-server/src/routes/agent.rs
index 118e28da8a..c1db248778 100644
--- a/crates/goose-server/src/routes/agent.rs
+++ b/crates/goose-server/src/routes/agent.rs
@@ -142,7 +142,7 @@ async fn start_agent(
     }
 
     let counter = state.session_counter.fetch_add(1, Ordering::SeqCst) + 1;
-    let name = format!("New chat {}", counter);
+    let name = format!("New Chat {}", counter);
 
     let mut session =
         SessionManager::create_session(PathBuf::from(&working_dir), name, SessionType::User)
diff --git a/ui/desktop/src/App.tsx b/ui/desktop/src/App.tsx
index 65c5008922..6153bc65ef 100644
--- a/ui/desktop/src/App.tsx
+++ b/ui/desktop/src/App.tsx
@@ -26,7 +26,7 @@ import SharedSessionView from './components/sessions/SharedSessionView';
 import SchedulesView from './components/schedule/SchedulesView';
 import ProviderSettings from './components/settings/providers/ProviderSettingsPage';
 import { AppLayout } from './components/Layout/AppLayout';
-import { ChatProvider } from './contexts/ChatContext';
+import { ChatProvider, DEFAULT_CHAT_TITLE } from './contexts/ChatContext';
 import LauncherView from './components/LauncherView';
 
 import 'react-toastify/dist/ReactToastify.css';
@@ -323,7 +323,7 @@ export function AppInner() {
 
   const [chat, setChat] = useState<ChatType>({
     sessionId: '',
-    name: 'Pair Chat',
+    name: DEFAULT_CHAT_TITLE,
     messages: [],
     messageHistoryIndex: 0,
     recipe: null,
diff --git a/ui/desktop/src/components/GooseSidebar/AppSidebar.tsx b/ui/desktop/src/components/GooseSidebar/AppSidebar.tsx
index 1b0c10231f..efce5de2cc 100644
--- a/ui/desktop/src/components/GooseSidebar/AppSidebar.tsx
+++ b/ui/desktop/src/components/GooseSidebar/AppSidebar.tsx
@@ -20,6 +20,7 @@ import { resumeSession, startNewSession } from '../../sessions';
 import { useNavigation } from '../../hooks/useNavigation';
 import { SessionIndicators } from '../SessionIndicators';
 import { useSessionStatusContext } from '../../contexts/SessionStatusContext';
+import { isDefaultSessionName } from '../../sessions';
 
 interface SidebarProps {
   onSelectSession: (sessionId: string) => void;
@@ -91,6 +92,9 @@ const SessionList = React.memo<{
           const isStreaming = status?.streamState === 'streaming';
           const hasError = status?.streamState === 'error';
           const hasUnread = status?.hasUnreadActivity ?? false;
+          const displayName = isDefaultSessionName(session.name)
+            ? DEFAULT_CHAT_TITLE
+            : session.name;
 
           return (
             <button
@@ -101,9 +105,9 @@ const SessionList = React.memo<{
                   ? 'bg-background-medium text-text-default'
                   : 'text-text-muted hover:bg-background-medium/50 hover:text-text-default'
               }`}
-              title={session.name}
+              title={displayName}
             >
-              <span className="flex-1 truncate min-w-0 block">{session.name}</span>
+              <span className="flex-1 truncate min-w-0 block">{displayName}</span>
               <SessionIndicators
                 isStreaming={isStreaming}
                 hasUnread={hasUnread}
@@ -175,13 +179,7 @@ const AppSidebar: React.FC<SidebarProps> = ({ currentPath }) => {
         const sessions = response.data.sessions.slice(0, 10);
         setRecentSessions(sessions);
 
-        const hasSessionWithDefaultName = sessions.some(
-          (s) =>
-            s.name === DEFAULT_CHAT_TITLE ||
-            s.name === 'Pair Chat' ||
-            s.name === 'New Chat' ||
-            s.name.startsWith('New chat ')
-        );
+        const hasSessionWithDefaultName = sessions.some((s) => isDefaultSessionName(s.name));
 
         if (hasSessionWithDefaultName) {
           window.dispatchEvent(new CustomEvent('session-needs-name-update'));
@@ -219,13 +217,7 @@ const AppSidebar: React.FC<SidebarProps> = ({ currentPath }) => {
           const sessions = response.data.sessions.slice(0, 10);
           setRecentSessions(sessions);
 
-          const sessionWithDefaultName = sessions.find(
-            (s) =>
-              s.name === DEFAULT_CHAT_TITLE ||
-              s.name === 'Pair Chat' ||
-              s.name === 'New Chat' ||
-              s.name.startsWith('New chat ')
-          );
+          const sessionWithDefaultName = sessions.find((s) => isDefaultSessionName(s.name));
 
           const shouldContinue = pollCount < maxPolls && (sessionWithDefaultName || pollCount < 5);
 
diff --git a/ui/desktop/src/components/sessions/SessionItem.tsx b/ui/desktop/src/components/sessions/SessionItem.tsx
index e8a010c91b..8149ad071a 100644
--- a/ui/desktop/src/components/sessions/SessionItem.tsx
+++ b/ui/desktop/src/components/sessions/SessionItem.tsx
@@ -2,6 +2,8 @@ import React from 'react';
 import { Card } from '../ui/card';
 import { formatDate } from '../../utils/date';
 import { Session } from '../../api';
+import { isDefaultSessionName } from '../../sessions';
+import { DEFAULT_CHAT_TITLE } from '../../contexts/ChatContext';
 
 interface SessionItemProps {
   session: Session;
@@ -9,10 +11,12 @@ interface SessionItemProps {
 }
 
 const SessionItem: React.FC<SessionItemProps> = ({ session, extraActions }) => {
+  const displayName = isDefaultSessionName(session.name) ? DEFAULT_CHAT_TITLE : session.name;
+
   return (
     <Card className="p-4 mb-2 hover:bg-accent/50 cursor-pointer flex justify-between items-center">
       <div>
-        <div className="font-medium">{session.name}</div>
+        <div className="font-medium">{displayName}</div>
         <div className="text-sm text-muted-foreground">
           {formatDate(session.updated_at)} • {session.message_count} messages
         </div>
diff --git a/ui/desktop/src/components/sessions/SessionListView.tsx b/ui/desktop/src/components/sessions/SessionListView.tsx
index bfd6ba385c..73e50cf98f 100644
--- a/ui/desktop/src/components/sessions/SessionListView.tsx
+++ b/ui/desktop/src/components/sessions/SessionListView.tsx
@@ -30,6 +30,8 @@ import {
   Session,
   updateSessionName,
 } from '../../api';
+import { isDefaultSessionName } from '../../sessions';
+import { DEFAULT_CHAT_TITLE } from '../../contexts/ChatContext';
 
 interface EditSessionModalProps {
   session: Session | null;
@@ -547,6 +549,8 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
         [onOpenInNewWindow, session]
       );
 
+      const displayName = isDefaultSessionName(session.name) ? DEFAULT_CHAT_TITLE : session.name;
+
       return (
         <Card
           onClick={handleCardClick}
@@ -554,7 +558,7 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
           ref={(el) => setSessionRefs(session.id, el)}
         >
           <div className="flex items-start justify-between gap-2 mb-1">
-            <h3 className="text-base break-words line-clamp-2 flex-1 min-w-0">{session.name}</h3>
+            <h3 className="text-base break-words line-clamp-2 flex-1 min-w-0">{displayName}</h3>
             <div className="flex gap-1 opacity-0 group-hover:opacity-100 transition-opacity flex-shrink-0">
               <button
                 onClick={handleOpenInNewWindowClick}
diff --git a/ui/desktop/src/hooks/useChatStream.ts b/ui/desktop/src/hooks/useChatStream.ts
index 32ea634d3d..498d22bdda 100644
--- a/ui/desktop/src/hooks/useChatStream.ts
+++ b/ui/desktop/src/hooks/useChatStream.ts
@@ -19,6 +19,7 @@ import {
   NotificationEvent,
 } from '../types/message';
 import { errorMessage } from '../utils/conversionUtils';
+import { isDefaultSessionName } from '../sessions';
 
 const resultsCache = new Map<string, { messages: Message[]; session: Session }>();
 
@@ -187,30 +188,20 @@ export function useChatStream({
 
       // After first AI response, check if session name was updated
       // This happens when the AI generates a title for a new conversation
-      if (session && messagesRef.current.length > 0) {
-        const isNewSession =
-          session.name === 'New Chat' ||
-          session.name === 'Pair Chat' ||
-          session.name === 'No Session' ||
-          session.name?.startsWith('New chat ');
+      if (session && messagesRef.current.length > 0 && isDefaultSessionName(session.name)) {
+        try {
+          const { getSession } = await import('../api');
+          const response = await getSession({
+            path: { session_id: sessionId },
+            throwOnError: true,
+          });
 
-        if (isNewSession) {
-          // Fetch updated session to get the new name
-          try {
-            const { getSession } = await import('../api');
-            const response = await getSession({
-              path: { session_id: sessionId },
-              throwOnError: true,
-            });
-
-            if (response.data && response.data.name !== session.name) {
-              setSession(response.data);
-              // Dispatch event to update sidebar
-              window.dispatchEvent(new CustomEvent('session-needs-name-update'));
-            }
-          } catch (error) {
-            console.error('Failed to fetch updated session:', error);
+          if (response.data && response.data.name !== session.name) {
+            setSession(response.data);
+            window.dispatchEvent(new CustomEvent('session-needs-name-update'));
           }
+        } catch (error) {
+          console.error('Failed to fetch updated session:', error);
         }
       }
 
diff --git a/ui/desktop/src/sessions.ts b/ui/desktop/src/sessions.ts
index cb170091c8..c3a27657fd 100644
--- a/ui/desktop/src/sessions.ts
+++ b/ui/desktop/src/sessions.ts
@@ -1,5 +1,18 @@
 import { Session, startAgent } from './api';
 import type { setViewType } from './hooks/useNavigation';
+import { DEFAULT_CHAT_TITLE } from './contexts/ChatContext';
+
+/**
+ * Check if a session name is a default/temporary name that should be updated
+ * @param name - The session name to check
+ * @returns true if the name is a default/temporary name
+ */
+export function isDefaultSessionName(name: string | undefined | null): boolean {
+  if (!name) return false;
+
+  // Check if it's exactly the default title or starts with it (for numbered versions)
+  return name === DEFAULT_CHAT_TITLE || name.startsWith(DEFAULT_CHAT_TITLE);
+}
 
 export function resumeSession(session: Session, setView: setViewType) {
   const eventDetail = {