diff --git a/frontend/src/pages/App.jsx b/frontend/src/pages/App.jsx
index b743fbe..38a85d5 100644
--- a/frontend/src/pages/App.jsx
+++ b/frontend/src/pages/App.jsx
@@ -6,6 +6,10 @@ import { apiService } from "../services/api";
 const POLL_INTERVAL = 600; // 0.6 seconds
 const INITIAL_ERROR_STATE = { visible: false, message: '' };
 const DEBOUNCE_DELAY = 300; // 300ms debounce for user input
+const CONVERSATION_FETCH_ERROR_DELAY_MS = 10000; // wait 10s before showing fetch errors
+const CONVERSATION_FETCH_ERROR_THRESHOLD = Math.ceil(
+    CONVERSATION_FETCH_ERROR_DELAY_MS / POLL_INTERVAL
+);
 
 function useDebounce(value, delay) {
     const [debouncedValue, setDebouncedValue] = useState(value);
@@ -39,15 +43,36 @@ export default function App() {
     const debouncedUserInput = useDebounce(userInput, DEBOUNCE_DELAY);
 
     const errorTimerRef = useRef(null);
+    const conversationFetchErrorCountRef = useRef(0);
 
     const handleError = useCallback((error, context) => {
         console.error(`${context}:`, error);
-        
-        const isConversationFetchError = error.status === 404;
-        const errorMessage = isConversationFetchError 
-            ? "Error fetching conversation. Retrying..."  // Updated message
+
+        const isConversationFetchError =
+            context === "fetching conversation" && (error.status === 404 || error.status === 408);
+
+        if (isConversationFetchError) {
+            if (error.status === 404) {
+                conversationFetchErrorCountRef.current += 1;
+
+                const hasExceededThreshold =
+                    conversationFetchErrorCountRef.current >= CONVERSATION_FETCH_ERROR_THRESHOLD;
+
+                if (!hasExceededThreshold) {
+                    return;
+                }
+            } else {
+                // For timeouts or other connectivity errors surface immediately
+                conversationFetchErrorCountRef.current = CONVERSATION_FETCH_ERROR_THRESHOLD;
+            }
+        } else {
+            conversationFetchErrorCountRef.current = 0;
+        }
+
+        const errorMessage = isConversationFetchError
+            ? "Error fetching conversation. Retrying..."
             : `Error ${context.toLowerCase()}. Please try again.`;
-    
+
         setError(prevError => {
             // If the same 404 error is already being displayed, don't reset state (prevents flickering)
             if (prevError.visible && prevError.message === errorMessage) {
@@ -55,12 +80,12 @@ export default function App() {
             }
             return { visible: true, message: errorMessage };
         });
-    
+
         // Clear any existing timeout
         if (errorTimerRef.current) {
             clearTimeout(errorTimerRef.current);
         }
-    
+
         // Only auto-dismiss non-404 errors after 3 seconds
         if (!isConversationFetchError) {
             errorTimerRef.current = setTimeout(() => setError(INITIAL_ERROR_STATE), 3000);
@@ -72,6 +97,7 @@ export default function App() {
         if (errorTimerRef.current) {
             clearTimeout(errorTimerRef.current);
         }
+        conversationFetchErrorCountRef.current = 0;
         setError(INITIAL_ERROR_STATE);
     }, []);
     
diff --git a/frontend/src/services/api.js b/frontend/src/services/api.js
index 02bdd73..62199ca 100644
--- a/frontend/src/services/api.js
+++ b/frontend/src/services/api.js
@@ -1,5 +1,17 @@
 const API_BASE_URL = 'http://127.0.0.1:8000';
 
+const resolveRequestTimeout = () => {
+    const env = typeof import.meta !== 'undefined' ? import.meta.env : undefined;
+    const configured = env?.VITE_API_TIMEOUT_MS;
+    const parsed = Number.parseInt(configured, 10);
+    if (Number.isFinite(parsed) && parsed > 0) {
+        return parsed;
+    }
+    return 15000;
+};
+
+const REQUEST_TIMEOUT_MS = resolveRequestTimeout(); // default to 15s, overridable via Vite env
+
 class ApiError extends Error {
     constructor(message, status) {
         super(message);
@@ -19,12 +31,31 @@ async function handleResponse(response) {
     return response.json();
 }
 
+async function fetchWithTimeout(url, options = {}, timeout = REQUEST_TIMEOUT_MS) {
+    const controller = new AbortController();
+    const timeoutId = setTimeout(() => controller.abort(), timeout);
+
+    try {
+        return await fetch(url, { ...options, signal: controller.signal });
+    } catch (error) {
+        if (error.name === 'AbortError') {
+            throw new ApiError('Request timed out', 408);
+        }
+        throw error;
+    } finally {
+        clearTimeout(timeoutId);
+    }
+}
+
 export const apiService = {
     async getConversationHistory() {
         try {
-            const res = await fetch(`${API_BASE_URL}/get-conversation-history`);
+            const res = await fetchWithTimeout(`${API_BASE_URL}/get-conversation-history`);
             return handleResponse(res);
         } catch (error) {
+            if (error instanceof ApiError) {
+                throw error;
+            }
             throw new ApiError(
                 'Failed to fetch conversation history',
                 error.status || 500
@@ -38,7 +69,7 @@ export const apiService = {
         }
 
         try {
-            const res = await fetch(
+            const res = await fetchWithTimeout(
                 `${API_BASE_URL}/send-prompt?prompt=${encodeURIComponent(message)}`,
                 { 
                     method: 'POST',
@@ -49,6 +80,9 @@ export const apiService = {
             );
             return handleResponse(res);
         } catch (error) {
+            if (error instanceof ApiError) {
+                throw error;
+            }
             throw new ApiError(
                 'Failed to send message',
                 error.status || 500
@@ -58,7 +92,7 @@ export const apiService = {
 
     async startWorkflow() {
         try {
-            const res = await fetch(
+            const res = await fetchWithTimeout(
                 `${API_BASE_URL}/start-workflow`,
                 { 
                     method: 'POST',
@@ -69,6 +103,9 @@ export const apiService = {
             );
             return handleResponse(res);
         } catch (error) {
+            if (error instanceof ApiError) {
+                throw error;
+            }
             throw new ApiError(
                 'Failed to start workflow',
                 error.status || 500
@@ -78,7 +115,7 @@ export const apiService = {
 
     async confirm() {
         try {
-            const res = await fetch(`${API_BASE_URL}/confirm`, { 
+            const res = await fetchWithTimeout(`${API_BASE_URL}/confirm`, { 
                 method: 'POST',
                 headers: {
                     'Content-Type': 'application/json'
@@ -86,10 +123,13 @@ export const apiService = {
             });
             return handleResponse(res);
         } catch (error) {
+            if (error instanceof ApiError) {
+                throw error;
+            }
             throw new ApiError(
                 'Failed to confirm action',
                 error.status || 500
             );
         }
     }
-}; 
\ No newline at end of file
+};