diff --git a/ui/desktop/src/components/context_management/ChatContextManager.tsx b/ui/desktop/src/components/context_management/ChatContextManager.tsx
index 9e8e666b8591..f883c872b48d 100644
--- a/ui/desktop/src/components/context_management/ChatContextManager.tsx
+++ b/ui/desktop/src/components/context_management/ChatContextManager.tsx
@@ -188,6 +188,7 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
         ...msg,
         display: true,
         sendToLLM: false,
+        isAncestor: true,
       }));
 
       // Append new ancestor messages to existing ones
@@ -198,6 +199,7 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
         ...msg,
         display: true,
         sendToLLM: false,
+        isAncestor: true,
       }));
 
       setAncestorMessages(newAncestorMessages);
diff --git a/ui/desktop/src/hooks/useChat.ts b/ui/desktop/src/hooks/useChat.ts
index 7db74e5a6e65..45a81ecd3bf0 100644
--- a/ui/desktop/src/hooks/useChat.ts
+++ b/ui/desktop/src/hooks/useChat.ts
@@ -37,6 +37,7 @@ export const useChat = ({ setIsLoadingSession, setView, setPairChat }: UseChatAr
             id: sessionDetails.session_id,
             title: sessionDetails.metadata?.description || `ID: ${sessionDetails.session_id}`,
             messages: sessionDetails.messages,
+            ancestorMessages: sessionDetails.ancestorMessages || [],
             messageHistoryIndex: sessionDetails.messages.length,
             recipeConfig: null, // Sessions don't have recipes by default
           };
diff --git a/ui/desktop/src/hooks/useChatEngine.ts b/ui/desktop/src/hooks/useChatEngine.ts
index 8d29f9866666..3551369b8885 100644
--- a/ui/desktop/src/hooks/useChatEngine.ts
+++ b/ui/desktop/src/hooks/useChatEngine.ts
@@ -44,7 +44,9 @@ export const useChatEngine = ({
 }: UseChatEngineProps) => {
   const [lastInteractionTime, setLastInteractionTime] = useState<number>(Date.now());
   const [sessionTokenCount, setSessionTokenCount] = useState<number>(0);
-  const [ancestorMessages, setAncestorMessages] = useState<Message[]>([]);
+  const [ancestorMessages, setAncestorMessages] = useState<Message[]>(
+    Array.isArray(chat.ancestorMessages) ? chat.ancestorMessages : []
+  );
   const [sessionInputTokens, setSessionInputTokens] = useState<number>(0);
   const [sessionOutputTokens, setSessionOutputTokens] = useState<number>(0);
   const [localInputTokens, setLocalInputTokens] = useState<number>(0);
@@ -96,7 +98,7 @@ export const useChatEngine = ({
   } = useMessageStream({
     api: getApiUrl('/reply'),
     id: chat.id,
-    initialMessages: chat.messages,
+    initialMessages: [...(chat.ancestorMessages || []), ...chat.messages],
     body: { session_id: chat.id, session_working_dir: window.appConfig.get('GOOSE_WORKING_DIR') },
     onFinish: async (_message, _reason) => {
       stopPowerSaveBlocker();
@@ -377,7 +379,8 @@ export const useChatEngine = ({
   }, [stop, messages, _setInput, setMessages, stopPowerSaveBlocker, enableLocalStorage]);
 
   const filteredMessages = useMemo(() => {
-    return [...ancestorMessages, ...messages].filter((message) => message.display ?? true);
+    const allMessages = [...ancestorMessages, ...messages];
+    return allMessages.filter((message) => message.display ?? true);
   }, [ancestorMessages, messages]);
 
   // Generate command history from filtered messages
diff --git a/ui/desktop/src/sessions.ts b/ui/desktop/src/sessions.ts
index 749f8bc73cf0..32108d7f0c04 100644
--- a/ui/desktop/src/sessions.ts
+++ b/ui/desktop/src/sessions.ts
@@ -41,6 +41,7 @@ export interface SessionDetails {
   session_id: string;
   metadata: SessionMetadata;
   messages: Message[];
+  ancestorMessages?: Message[];
 }
 
 /**
@@ -113,13 +114,21 @@ export async function fetchSessionDetails(sessionId: string): Promise<SessionDet
       path: { session_id: sessionId },
     });
 
+    const allMessages = response.data.messages.map((message) =>
+      convertApiMessageToFrontendMessage(message, true, true)
+    );
+
+    const ancestorMessages = allMessages.filter(msg => msg.isAncestor === true);
+    const regularMessages = allMessages.filter(msg => msg.isAncestor !== true);
+
+    const validAncestorMessages = Array.isArray(ancestorMessages) ? ancestorMessages : [];
+
     // Convert the SessionHistoryResponse to a SessionDetails object
     return {
       session_id: response.data.sessionId,
       metadata: ensureWorkingDir(response.data.metadata),
-      messages: response.data.messages.map((message) =>
-        convertApiMessageToFrontendMessage(message, true, true)
-      ), // slight diffs between backend and frontend Message obj
+      messages: regularMessages,
+      ancestorMessages: validAncestorMessages,
     };
   } catch (error) {
     console.error(`Error fetching session details for ${sessionId}:`, error);
diff --git a/ui/desktop/src/types/chat.ts b/ui/desktop/src/types/chat.ts
index ac0367590b02..be0249cf4c01 100644
--- a/ui/desktop/src/types/chat.ts
+++ b/ui/desktop/src/types/chat.ts
@@ -6,6 +6,7 @@ export interface ChatType {
   title: string;
   messageHistoryIndex: number;
   messages: Message[];
+  ancestorMessages?: Message[];
   recipeConfig?: Recipe | null; // Add recipe configuration to chat state
   recipeParameters?: Record<string, string> | null; // Add recipe parameters to chat state
 }
diff --git a/ui/desktop/src/types/message.ts b/ui/desktop/src/types/message.ts
index 3c45bc75d7ad..ce93261f57f4 100644
--- a/ui/desktop/src/types/message.ts
+++ b/ui/desktop/src/types/message.ts
@@ -110,6 +110,7 @@ export interface Message {
   content: MessageContent[];
   display?: boolean;
   sendToLLM?: boolean;
+  isAncestor?: boolean;
 }
 
 // Helper functions to create messages