diff --git a/chatto/src/main/java/org/ros/chatto/security/TokenAuthenticationFilter.java b/chatto/src/main/java/org/ros/chatto/security/TokenAuthenticationFilter.java
index 61ad59c..562ed51 100644
--- a/chatto/src/main/java/org/ros/chatto/security/TokenAuthenticationFilter.java
+++ b/chatto/src/main/java/org/ros/chatto/security/TokenAuthenticationFilter.java
@@ -97,6 +97,11 @@ public class TokenAuthenticationFilter extends OncePerRequestFilter {
 				} else {
 					userTokenService.deleteToken(userToken.getUserName());
 					TokenCacheUtil.evictSingleTokenValue(userToken.getTokenContent());
+					response.setHeader(HttpHeaders.CONTENT_TYPE, MediaType.TEXT_PLAIN_VALUE);
+					response.setStatus(440);
+					response.getWriter().write("Token authentication error: Token has expired");
+					logger.warn("Token authentication error: Token has expired");
+					return;
 				}
 
 			}
diff --git a/chatto/src/main/resources/static/js/chat.js b/chatto/src/main/resources/static/js/chat.js
index cdbaab9..23428b6 100644
--- a/chatto/src/main/resources/static/js/chat.js
+++ b/chatto/src/main/resources/static/js/chat.js
@@ -330,6 +330,7 @@ async function getAllMessages(toUser) {
         method: 'GET',
         headers: headers
     });
+    console.log(response);
     let data = await response.json();
     return data;
 }
@@ -342,6 +343,12 @@ async function getNewMessages(toUser, lastMessageTimeStamp) {
         method: 'GET',
         headers: headers
     });
+    console.log(response);
+    if(response.status == 440)
+    {
+        window.alert('Token has expired. Please login again');
+        return;
+    }
     let data = await response.json();
     return data;
 }