diff --git a/ui/desktop/src/App.tsx b/ui/desktop/src/App.tsx
index 12aa2fe3..0c59d961 100644
--- a/ui/desktop/src/App.tsx
+++ b/ui/desktop/src/App.tsx
@@ -357,10 +357,12 @@ export function AppInner() {
     if (loadingHub) {
       (async () => {
         try {
-          await loadCurrentChat({
+          const loadedChat = await loadCurrentChat({
             setAgentWaitingMessage,
             setIsExtensionsLoading,
           });
+          // Update the chat state with the loaded session to ensure sessionId is available globally
+          setChat(loadedChat);
         } catch (e) {
           if (e instanceof NoProviderOrModelError) {
             // the onboarding flow will trigger
@@ -370,7 +372,7 @@ export function AppInner() {
         }
       })();
     }
-  }, [resetChat, loadCurrentChat, setAgentWaitingMessage, navigate, loadingHub]);
+  }, [resetChat, loadCurrentChat, setAgentWaitingMessage, navigate, loadingHub, setChat]);
 
   useEffect(() => {
     const handleOpenSharedSession = async (_event: IpcRendererEvent, ...args: unknown[]) => {
@@ -582,7 +584,19 @@ export function AppInner() {
               }
             />
             <Route path="settings" element={<SettingsRoute />} />
-            <Route path="extensions" element={<ExtensionsRoute />} />
+            <Route
+              path="extensions"
+              element={
+                <ChatProvider
+                  chat={chat}
+                  setChat={setChat}
+                  contextKey="extensions"
+                  agentWaitingMessage={agentWaitingMessage}
+                >
+                  <ExtensionsRoute />
+                </ChatProvider>
+              }
+            />
             <Route path="sessions" element={<SessionsRoute />} />
             <Route path="schedules" element={<SchedulesRoute />} />
             <Route path="recipes" element={<RecipesRoute />} />
diff --git a/ui/desktop/src/components/BaseChat.tsx b/ui/desktop/src/components/BaseChat.tsx
index 66aeb5cf..e267ffab 100644
--- a/ui/desktop/src/components/BaseChat.tsx
+++ b/ui/desktop/src/components/BaseChat.tsx
@@ -441,7 +441,7 @@ function BaseChatContent({
                             onClick={async () => {
                               clearError();
 
-                              await handleManualCompaction(messages, setMessages, append);
+                              await handleManualCompaction(messages, setMessages, append, chat.sessionId);
                             }}
                           >
                             Summarize Conversation
diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index aff49368..2ed48b1d 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -568,7 +568,7 @@ export default function ChatInput({
           // Hide the alert popup by dispatching a custom event that the popover can listen to
           // Importantly, this leaves the alert so the dot still shows up, but hides the popover
           window.dispatchEvent(new CustomEvent('hide-alert-popover'));
-          handleManualCompaction(messages, setMessages, append);
+          handleManualCompaction(messages, setMessages, append, sessionId || '');
         },
         compactIcon: <ScrollText size={12} />,
         autoCompactThreshold: autoCompactThreshold,
diff --git a/ui/desktop/src/components/context_management/ContextManager.tsx b/ui/desktop/src/components/context_management/ContextManager.tsx
index f95e396c..4d5ad9d9 100644
--- a/ui/desktop/src/components/context_management/ContextManager.tsx
+++ b/ui/desktop/src/components/context_management/ContextManager.tsx
@@ -12,12 +12,14 @@ interface ContextManagerActions {
   handleAutoCompaction: (
     messages: Message[],
     setMessages: (messages: Message[]) => void,
-    append: (message: Message) => void
+    append: (message: Message) => void,
+    sessionId: string
   ) => Promise<void>;
   handleManualCompaction: (
     messages: Message[],
     setMessages: (messages: Message[]) => void,
-    append?: (message: Message) => void
+    append?: (message: Message) => void,
+    sessionId?: string
   ) => Promise<void>;
   hasCompactionMarker: (message: Message) => boolean;
 }
@@ -37,6 +39,7 @@ export const ContextManagerProvider: React.FC<{ children: React.ReactNode }> = (
       messages: Message[],
       setMessages: (messages: Message[]) => void,
       append: (message: Message) => void,
+      sessionId: string,
       isManual: boolean = false
     ) => {
       setIsCompacting(true);
@@ -47,6 +50,7 @@ export const ContextManagerProvider: React.FC<{ children: React.ReactNode }> = (
         const summaryResponse = await manageContextFromBackend({
           messages: messages,
           manageAction: 'summarize',
+          sessionId: sessionId,
         });
 
         // Convert API messages to frontend messages
@@ -100,9 +104,10 @@ export const ContextManagerProvider: React.FC<{ children: React.ReactNode }> = (
     async (
       messages: Message[],
       setMessages: (messages: Message[]) => void,
-      append: (message: Message) => void
+      append: (message: Message) => void,
+      sessionId: string
     ) => {
-      await performCompaction(messages, setMessages, append, false);
+      await performCompaction(messages, setMessages, append, sessionId, false);
     },
     [performCompaction]
   );
@@ -111,9 +116,10 @@ export const ContextManagerProvider: React.FC<{ children: React.ReactNode }> = (
     async (
       messages: Message[],
       setMessages: (messages: Message[]) => void,
-      append?: (message: Message) => void
+      append?: (message: Message) => void,
+      sessionId?: string
     ) => {
-      await performCompaction(messages, setMessages, append || (() => {}), true);
+      await performCompaction(messages, setMessages, append || (() => {}), sessionId || '', true);
     },
     [performCompaction]
   );
diff --git a/ui/desktop/src/components/context_management/__tests__/ContextManager.test.tsx b/ui/desktop/src/components/context_management/__tests__/ContextManager.test.tsx
index 453d8cfa..1ef01070 100644
--- a/ui/desktop/src/components/context_management/__tests__/ContextManager.test.tsx
+++ b/ui/desktop/src/components/context_management/__tests__/ContextManager.test.tsx
@@ -166,12 +166,13 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend);
+        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend, 'test-session-id');
       });
 
       expect(mockManageContextFromBackend).toHaveBeenCalledWith({
         messages: mockMessages,
         manageAction: 'summarize',
+        sessionId: 'test-session-id',
       });
 
       // Verify conversion calls with correct parameters
@@ -225,7 +226,7 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend);
+        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend, "test-session-id");
       });
 
       expect(result.current.compactionError).toBe('Backend error');
@@ -256,7 +257,7 @@ describe('ContextManager', () => {
 
       // Start compaction
       act(() => {
-        result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend);
+        result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend, "test-session-id");
       });
 
       // Should be compacting
@@ -306,7 +307,7 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleAutoCompaction(messages, mockSetMessages, mockAppend);
+        await result.current.handleAutoCompaction(messages, mockSetMessages, mockAppend, "test-session-id");
       });
 
       // No server messages -> setMessages called with empty list
@@ -369,12 +370,13 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleManualCompaction(mockMessages, mockSetMessages, mockAppend);
+        await result.current.handleManualCompaction(mockMessages, mockSetMessages, mockAppend, 'test-session-id');
       });
 
       expect(mockManageContextFromBackend).toHaveBeenCalledWith({
         messages: mockMessages,
         manageAction: 'summarize',
+        sessionId: 'test-session-id',
       });
 
       // Verify all three messages are set
@@ -481,7 +483,7 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleManualCompaction(mockMessages, mockSetMessages, mockAppend);
+        await result.current.handleManualCompaction(mockMessages, mockSetMessages, mockAppend, 'test-session-id');
       });
 
       // Verify all three messages are set
@@ -508,7 +510,7 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend);
+        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend, "test-session-id");
       });
 
       expect(result.current.compactionError).toBe('Unknown error during compaction');
@@ -539,7 +541,7 @@ describe('ContextManager', () => {
       const { result } = renderContextManager();
 
       await act(async () => {
-        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend);
+        await result.current.handleAutoCompaction(mockMessages, mockSetMessages, mockAppend, "test-session-id");
       });
 
       // Should complete without error even if content is not text
diff --git a/ui/desktop/src/components/context_management/index.ts b/ui/desktop/src/components/context_management/index.ts
index 68ddbb8c..c54d95eb 100644
--- a/ui/desktop/src/components/context_management/index.ts
+++ b/ui/desktop/src/components/context_management/index.ts
@@ -18,12 +18,14 @@ import { generateId } from 'ai';
 export async function manageContextFromBackend({
   messages,
   manageAction,
+  sessionId,
 }: {
   messages: FrontendMessage[];
   manageAction: 'truncation' | 'summarize';
+  sessionId: string;
 }): Promise<ContextManageResponse> {
   try {
-    const contextManagementRequest = { manageAction, messages };
+    const contextManagementRequest = { manageAction, messages, sessionId };
 
     // Cast to the API-expected type
     const result = await manageContext({