diff --git a/deploy-board/deploy_board/templates/clusters/base_images_events.html b/deploy-board/deploy_board/templates/clusters/base_images_events.html
index 2a5a3afc89..0384b571b7 100644
--- a/deploy-board/deploy_board/templates/clusters/base_images_events.html
+++ b/deploy-board/deploy_board/templates/clusters/base_images_events.html
@@ -53,7 +53,7 @@ <h4 class="panel-title pull-left">Base Images Events</h4>
                 globalNotificationBanner.info = "Request sent successfully";
             },
             error: function (data) { // if error occured
-                globalNotificationBanner.error = data;
+                globalNotificationBanner.error = data.responseJSON.error;
             },
         });
     });
@@ -72,7 +72,7 @@ <h4 class="panel-title pull-left">Base Images Events</h4>
                 globalNotificationBanner.info = "Request sent successfully";
             },
             error: function (data) { // if error occured
-                globalNotificationBanner.error = data;
+                globalNotificationBanner.error = data.responseJSON.error;
             },
         });
     });
@@ -137,4 +137,4 @@ <h4 class="modal-title">Promote Image Confirm</h4>
     </div>
 </div>
 
-{% endblock %}
\ No newline at end of file
+{% endblock %}
diff --git a/deploy-board/deploy_board/templates/clusters/cluster_configuration.html b/deploy-board/deploy_board/templates/clusters/cluster_configuration.html
index 9a30eb54dc..630ecd2fa5 100644
--- a/deploy-board/deploy_board/templates/clusters/cluster_configuration.html
+++ b/deploy-board/deploy_board/templates/clusters/cluster_configuration.html
@@ -669,7 +669,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                             scope.imageNameChange(data[0]);
                         },
                         error: function (data) {
-                            globalNotificationBanner.error = data
+                            globalNotificationBanner.error = data.responseJSON.error;
                         }
                     });
 
@@ -697,7 +697,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                             capacitySetting.selectedSecurityZoneValue = data[0]?.abstract_name;
                         },
                         error: function (data) {
-                            globalNotificationBanner.error = data
+                            globalNotificationBanner.error = data.responseJSON.error;
                         }
                     });
 
@@ -719,7 +719,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                                 placements ? placements.getFullList(false, cell == initialCell ? currentPlacements : null) : null;
                         },
                         error: function (data) {
-                            globalNotificationBanner.error = data
+                            globalNotificationBanner.error = data.responseJSON.error;
                         }
                     })
                 },
@@ -747,7 +747,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                             scope.imageNameChange(imageName);
                         },
                         error: function (data) {
-                            globalNotificationBanner.error = data
+                            globalNotificationBanner.error = data.responseJSON.error;
                         }
                     });
                     // grab all the host types
@@ -777,7 +777,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                             })
                         },
                         error: function (data) {
-                            globalNotificationBanner.error = data
+                            globalNotificationBanner.error = data.responseJSON.error;
                         }
                     });
                 },
@@ -811,7 +811,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                             capacitySetting.pinImageEnabled = isPinImageEnabled(goldenImage);
                         },
                         error: function(data) {
-                            globalNotificationBanner.error = data
+                            globalNotificationBanner.error = data.responseJSON.error;
                         }
                     });
                 },
diff --git a/deploy-board/deploy_board/templates/configs/capacity.html b/deploy-board/deploy_board/templates/configs/capacity.html
index 774533651d..0ecdf04525 100644
--- a/deploy-board/deploy_board/templates/configs/capacity.html
+++ b/deploy-board/deploy_board/templates/configs/capacity.html
@@ -107,7 +107,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                         window.location.href=window.location.href
                     },
                     error: function(data) {
-                        globalNotificationBanner.error = data
+                        globalNotificationBanner.error = data.responseJSON.error;
                     }
                 });
         },
@@ -138,7 +138,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                         window.location.href=window.location.href
                     },
                     error: function(data) {
-                        globalNotificationBanner.error = data
+                        globalNotificationBanner.error = data.responseJSON.error;
                     }
                 });
         },
diff --git a/deploy-board/deploy_board/templates/configs/capacity.tmpl b/deploy-board/deploy_board/templates/configs/capacity.tmpl
index bf36668277..6c829e188c 100644
--- a/deploy-board/deploy_board/templates/configs/capacity.tmpl
+++ b/deploy-board/deploy_board/templates/configs/capacity.tmpl
@@ -107,15 +107,11 @@
                         xhr.setRequestHeader("X-CSRFToken", csrftoken);
                     },
                     success: function (data) {
-                        if(data != null && data.success == false) {
-                            globalNotificationBanner.error = data;
-                        } else {
-                            globalNotificationBanner.info = "Saved Successfully";
-                            window.location.href='/env/{{ env.envName }}/{{ env.stageName }}/config/capacity/'
-                        }
+                        globalNotificationBanner.info = "Saved Successfully";
+                        window.location.href='/env/{{ env.envName }}/{{ env.stageName }}/config/capacity/'
                     },
                     error: function (data) {
-                        globalNotificationBanner.error = data;
+                        globalNotificationBanner.error = data.responseJSON.error;
                     }
                 });
             },
@@ -123,4 +119,3 @@
       }
     )
 </script>
-
diff --git a/deploy-board/deploy_board/templates/configs/env_config.tmpl b/deploy-board/deploy_board/templates/configs/env_config.tmpl
index 2a1a69a50b..8161ae4146 100644
--- a/deploy-board/deploy_board/templates/configs/env_config.tmpl
+++ b/deploy-board/deploy_board/templates/configs/env_config.tmpl
@@ -365,20 +365,15 @@
                     btn.button('loading');
                 },
                 success: function (data) {
-                    if (data != null && data.success == false) {
-                        $('#errorBannerId').append(data.error);
-                        if ($('#stageTypeValueId').val() == 'DEFAULT') {
-                            $('#errorBannerId').append("<a href='{{stage_type_info_link}}'>pinch/teletraan-stagetypes</a>");
-                        }
-                        $('#errorBannerId').show();
-                    } else {
-                        $("#envConfigId").parent().html(data.html);
-                        $('#errorBannerId').empty().hide();
-                    }
+                    $("#envConfigId").parent().html(data.html);
+                    $('#errorBannerId').empty().hide();
                     btn.button('reset');
                 },
                 error: function (data) {
-                    $('#errorBannerId').append(data.responseText);
+                    $('#errorBannerId').append(data.responseJSON.error);
+                    if ($('#stageTypeValueId').val() == 'DEFAULT') {
+                        $('#errorBannerId').append("<a href='{{stage_type_info_link}}'>pinch/teletraan-stagetypes</a>");
+                    }
                     $('#errorBannerId').show();
                 }
             });
diff --git a/deploy-board/deploy_board/templates/configs/new_capacity_adv.html b/deploy-board/deploy_board/templates/configs/new_capacity_adv.html
index 930f7bc570..df4226d1ce 100644
--- a/deploy-board/deploy_board/templates/configs/new_capacity_adv.html
+++ b/deploy-board/deploy_board/templates/configs/new_capacity_adv.html
@@ -281,7 +281,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     onSuccess(data)
                 },
                 error: function(data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
         },
@@ -322,7 +322,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     scope.imageNameChange(data && data.length > 0 ? data[0] : null);
                 },
                 error: function (data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
 
@@ -351,7 +351,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     capacitySetting.selectedSecurityZoneValue = data && data.length > 0 ? data[0].abstract_name : null;
                 },
                 error: function (data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
 
@@ -373,7 +373,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     capacitySetting.placements = placements ? placements.getFullList(false, null) : null;
                 },
                 error: function (data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
         },
@@ -400,7 +400,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     scope.imageNameChange(imageName);
                 },
                 error: function (data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
             // grab all the host types
@@ -424,7 +424,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     })
                 },
                 error: function (data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
         },
@@ -458,7 +458,7 @@ <h4 class="panel-title pull-left">Capacity</h4>
                     capacitySetting.pinImageEnabled = isPinImageEnabled(goldenImage);
                 },
                 error: function (data) {
-                    globalNotificationBanner.error = data
+                    globalNotificationBanner.error = data.responseJSON.error;
                 }
             });
         },
diff --git a/deploy-board/deploy_board/templates/error.tmpl b/deploy-board/deploy_board/templates/error.tmpl
index c3097ba1c5..0427d3fde9 100644
--- a/deploy-board/deploy_board/templates/error.tmpl
+++ b/deploy-board/deploy_board/templates/error.tmpl
@@ -1,7 +1,8 @@
 <div class="panel panel-default">
     <div class="alert alert-danger" role="alert">{{ message }}</div>
-    <div class="alert" role="alert">Sorry for the inconvenience, please contact your friendly Teletraan owners for
-        immediate assistance!</div>
+        <div class="alert" role="alert">
+            Sorry for the inconvenience, please read the error message. If the problem persists, please contact your friendly Teletraan owners for further assistance.
+        </div>
     <div class="alert alert-danger" role="alert">
         <pre>
             {{ stacktrace }}
diff --git a/deploy-board/deploy_board/webapp/helpers/base_client.py b/deploy-board/deploy_board/webapp/helpers/base_client.py
index c16e637af0..a99f39cf86 100644
--- a/deploy-board/deploy_board/webapp/helpers/base_client.py
+++ b/deploy-board/deploy_board/webapp/helpers/base_client.py
@@ -56,11 +56,10 @@ def api(path, token=None, params=None, data=None):
 
             if response.status_code == 401:
                 raise FailedAuthenticationException(
-                    "Oops! Teletraan was unable to authenticate you. Contact an environment ADMIN for "
-                    "assistance. " + response.text)
+                    f"Oops! Teletraan was unable to authenticate you. Please re-login. Server message: {response.json()['message']}")
 
             if response.status_code == 403:
-                raise NotAuthorizedException(f'{UNAUTHORIZED_ERROR_TEXT}: {response.text}')
+                raise NotAuthorizedException(f"{UNAUTHORIZED_ERROR_TEXT}. Server message: {response.json()['message']}")
 
             if response.status_code == 400 or response.status_code == 422:
                 raise IllegalArgumentException(response.text)
diff --git a/deploy-board/deploy_board/webapp/helpers/exceptions.py b/deploy-board/deploy_board/webapp/helpers/exceptions.py
index 54325a9192..099c95b763 100644
--- a/deploy-board/deploy_board/webapp/helpers/exceptions.py
+++ b/deploy-board/deploy_board/webapp/helpers/exceptions.py
@@ -15,12 +15,6 @@
 # -*- coding: utf-8 -*-
 """Backend server all exception
 """
-
-
-class FailedAuthenticationException(Exception):
-    pass
-
-
 class NotFoundException(Exception):
     pass
 
@@ -35,6 +29,11 @@ class IllegalArgumentException(TeletraanException):
     def __init__(self, message: str) -> None:
         super().__init__(message, status=400)
 
+class FailedAuthenticationException(TeletraanException):
+    def __init__(self, message: str) -> None:
+        super().__init__(message, status=401)
+
+
 class NotAuthorizedException(TeletraanException):
     def __init__(self, message: str) -> None:
         super().__init__(message, status=403)
diff --git a/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/CompositeAuthenticationFactory.java b/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/CompositeAuthenticationFactory.java
index bbacc9e91f..e7f1b8d29b 100644
--- a/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/CompositeAuthenticationFactory.java
+++ b/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/CompositeAuthenticationFactory.java
@@ -27,6 +27,7 @@
 import io.dropwizard.auth.AuthFilter;
 import io.dropwizard.auth.Authenticator;
 import io.dropwizard.auth.CachingAuthenticator;
+import io.dropwizard.auth.JSONUnauthorizedHandler;
 import io.dropwizard.auth.chained.ChainedAuthFilter;
 import java.util.Arrays;
 import javax.ws.rs.container.ContainerRequestFilter;
@@ -50,6 +51,7 @@ public ContainerRequestFilter create(TeletraanServiceContext context) throws Exc
                 new EnvoyAuthFilter.Builder<TeletraanPrincipal>()
                         .setAuthenticator(authenticator)
                         .setAuthorizer(context.getAuthorizationFactory().create(context))
+                        .setUnauthorizedHandler(new JSONUnauthorizedHandler())
                         .buildAuthFilter();
 
         return new ChainedAuthFilter(
diff --git a/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/TokenAuthenticationFactory.java b/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/TokenAuthenticationFactory.java
index 12678b46de..3503982709 100644
--- a/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/TokenAuthenticationFactory.java
+++ b/deploy-service/teletraanservice/src/main/java/com/pinterest/teletraan/config/TokenAuthenticationFactory.java
@@ -31,6 +31,7 @@
 import io.dropwizard.auth.Authenticator;
 import io.dropwizard.auth.Authorizer;
 import io.dropwizard.auth.CachingAuthenticator;
+import io.dropwizard.auth.JSONUnauthorizedHandler;
 import io.dropwizard.auth.chained.ChainedAuthFilter;
 import io.dropwizard.auth.oauth.OAuthCredentialAuthFilter;
 import java.util.Arrays;
@@ -115,6 +116,7 @@ AuthFilter<String, ScriptTokenPrincipal<ValueBasedRole>> createScriptTokenAuthFi
                                         context.getAuthorizationFactory()
                                                 .create(context, ServicePrincipal.class))
                         .setPrefix("token")
+                        .setUnauthorizedHandler(new JSONUnauthorizedHandler())
                         .buildAuthFilter();
     }
 
@@ -135,6 +137,7 @@ AuthFilter<String, UserPrincipal> createOauthTokenAuthFilter(TeletraanServiceCon
                                         context.getAuthorizationFactory()
                                                 .create(context, UserPrincipal.class))
                         .setPrefix("token")
+                        .setUnauthorizedHandler(new JSONUnauthorizedHandler())
                         .buildAuthFilter();
     }
 
@@ -152,6 +155,7 @@ AuthFilter<String, UserPrincipal> createJwtTokenAuthFilter(TeletraanServiceConte
                         (Authorizer<UserPrincipal>) context.getAuthorizationFactory()
                                 .create(context, UserPrincipal.class))
                 .setPrefix("Bearer")
+                .setUnauthorizedHandler(new JSONUnauthorizedHandler())
                 .buildAuthFilter();
     }
 }