diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_stats.tsx b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_stats.tsx
index 095844b4e04d483..d8725141eb5e3f0 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_stats.tsx
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_stats.tsx
@@ -122,10 +122,8 @@ export const ConnectorStats: React.FC<ConnectorStatsProps> = ({ connector, index
                 </EuiText>
               </EuiFlexItem>
               <EuiFlexItem grow={false}>
-                <EuiBadge
-                  color={connectorStatusToColor(connector?.status, !!connector?.index_name)}
-                >
-                  {connectorStatusToText(connector?.status, !!connector?.index_name)}
+                <EuiBadge color={connectorStatusToColor(connector)}>
+                  {connectorStatusToText(connector)}
                 </EuiBadge>
               </EuiFlexItem>
             </EuiFlexGroup>
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_view_logic.ts b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_view_logic.ts
index f7d6f30ee7d54fd..42d881300ac5d1b 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_view_logic.ts
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/connector_view_logic.ts
@@ -158,7 +158,11 @@ export const ConnectorViewLogic = kea<MakeLogicType<ConnectorViewValues, Connect
     connectorId: [() => [selectors.connector], (connector) => connector?.id],
     error: [
       () => [selectors.connector],
-      (connector: Connector | undefined) => connector?.error || connector?.last_sync_error || null,
+      (connector: Connector | undefined) =>
+        connector?.error ||
+        connector?.last_sync_error ||
+        connector?.last_access_control_sync_error ||
+        null,
     ],
     indexName: [
       () => [selectors.connector],
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/overview.tsx b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/overview.tsx
index a97f7b8c862fd12..1931f0f94550546 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/overview.tsx
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connector_detail/overview.tsx
@@ -186,7 +186,10 @@ export const ConnectorDetailOverview: React.FC = () => {
       {connector && connector.service_type !== ENTERPRISE_SEARCH_CONNECTOR_CRAWLER_SERVICE_TYPE && (
         <>
           <EuiSpacer />
-          <SyncJobs />
+          <SyncJobs
+            errorOnAccessSync={Boolean(connector.last_access_control_sync_error)}
+            errorOnContentSync={Boolean(connector.last_sync_error)}
+          />
         </>
       )}
     </>
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connector_stats.tsx b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connector_stats.tsx
index 8b2ad4490a1a6b1..db76e97ec719e76 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connector_stats.tsx
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connector_stats.tsx
@@ -213,6 +213,7 @@ export const ConnectorStats: React.FC<ConnectorStatsProps> = ({ isCrawler }) =>
               <EuiBadge
                 onClick={() => {}}
                 onClickAriaLabel={getSyncJobErrorsLabel(errorCount, isCrawler)}
+                color={errorCount > 0 ? 'danger' : 'default'}
               >
                 {getSyncJobErrorsLabel(errorCount, isCrawler)}
               </EuiBadge>
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connectors_table.tsx b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connectors_table.tsx
index daf3f59eef45ed0..82f258487f39ec5 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connectors_table.tsx
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/connectors/connectors_table.tsx
@@ -135,12 +135,8 @@ export const ConnectorsTable: React.FC<ConnectorsTableProps> = ({
         }
       ),
       render: (connector: ConnectorViewItem) => {
-        const label = connectorStatusToText(connector.status, !!connector.index_name);
-        return (
-          <EuiBadge color={connectorStatusToColor(connector.status, !!connector.index_name)}>
-            {label}
-          </EuiBadge>
-        );
+        const label = connectorStatusToText(connector);
+        return <EuiBadge color={connectorStatusToColor(connector)}>{label}</EuiBadge>;
       },
       truncateText: true,
       width: '15%',
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/index_view_logic.ts b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/index_view_logic.ts
index 57f6d8f11bfcef9..597757e83534a75 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/index_view_logic.ts
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/index_view_logic.ts
@@ -264,7 +264,11 @@ export const IndexViewLogic = kea<MakeLogicType<IndexViewValues, IndexViewAction
     ],
     error: [
       () => [selectors.connector],
-      (connector: Connector | undefined) => connector?.error || connector?.last_sync_error || null,
+      (connector: Connector | undefined) =>
+        connector?.error ||
+        connector?.last_sync_error ||
+        connector?.last_access_control_sync_error ||
+        null,
     ],
     hasAdvancedFilteringFeature: [
       () => [selectors.connector],
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/overview.tsx b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/overview.tsx
index b280d3fbf36b78e..f8ccf71026e83b9 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/overview.tsx
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/overview.tsx
@@ -81,7 +81,11 @@ export const SearchIndexOverview: React.FC = () => {
                   defaultMessage="Convert it to a {link}, to be self-managed on your own infrastructure. Native connectors are available only in your Elastic Cloud deployment."
                   values={{
                     link: (
-                      <EuiLink href={docLinks.buildConnector} target="_blank">
+                      <EuiLink
+                        data-test-subj="enterpriseSearchSearchIndexOverviewConnectorClientLink"
+                        href={docLinks.buildConnector}
+                        target="_blank"
+                      >
                         {i18n.translate(
                           'xpack.enterpriseSearch.content.searchIndex.nativeCloudCallout.connectorClient',
                           { defaultMessage: 'connector client' }
@@ -93,7 +97,12 @@ export const SearchIndexOverview: React.FC = () => {
               </p>
             </EuiText>
             <EuiSpacer size="s" />
-            <EuiButton color="warning" fill onClick={() => showModal()}>
+            <EuiButton
+              data-test-subj="enterpriseSearchSearchIndexOverviewConvertConnectorButton"
+              color="warning"
+              fill
+              onClick={() => showModal()}
+            >
               {i18n.translate(
                 'xpack.enterpriseSearch.content.indices.searchIndex.convertConnector.buttonLabel',
                 { defaultMessage: 'Convert connector' }
@@ -126,7 +135,10 @@ export const SearchIndexOverview: React.FC = () => {
       {isConnectorIndex(indexData) && (
         <>
           <EuiSpacer />
-          <SyncJobs />
+          <SyncJobs
+            errorOnAccessSync={Boolean(indexData.connector.last_access_control_sync_error)}
+            errorOnContentSync={Boolean(indexData.connector.last_sync_error)}
+          />
         </>
       )}
     </>
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/sync_jobs/sync_jobs.tsx b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/sync_jobs/sync_jobs.tsx
index 2013d601df4aa80..49f49591007361d 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/sync_jobs/sync_jobs.tsx
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/components/search_index/sync_jobs/sync_jobs.tsx
@@ -21,7 +21,15 @@ import { IndexViewLogic } from '../index_view_logic';
 
 import { SyncJobsViewLogic } from './sync_jobs_view_logic';
 
-export const SyncJobs: React.FC = () => {
+export interface SyncJobsProps {
+  errorOnAccessSync?: boolean;
+  errorOnContentSync?: boolean;
+}
+
+export const SyncJobs: React.FC<SyncJobsProps> = ({
+  errorOnAccessSync = false,
+  errorOnContentSync = false,
+}) => {
   const { hasDocumentLevelSecurityFeature } = useValues(IndexViewLogic);
   const { productFeatures } = useValues(KibanaLogic);
   const shouldShowAccessSyncs =
@@ -74,6 +82,7 @@ export const SyncJobs: React.FC = () => {
                 'xpack.enterpriseSearch.content.syncJobs.lastSync.tableSelector.content.label',
                 { defaultMessage: 'Content syncs' }
               ),
+              ...(errorOnContentSync ? { iconSide: 'right', iconType: 'warning' } : {}),
             },
 
             {
@@ -82,6 +91,7 @@ export const SyncJobs: React.FC = () => {
                 'xpack.enterpriseSearch.content.syncJobs.lastSync.tableSelector.accessControl.label',
                 { defaultMessage: 'Access control syncs' }
               ),
+              ...(errorOnAccessSync ? { iconSide: 'right', iconType: 'warning' } : {}),
             },
           ]}
         />
diff --git a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/utils/connector_status_helpers.ts b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/utils/connector_status_helpers.ts
index ef8e84177eae101..587539498c78651 100644
--- a/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/utils/connector_status_helpers.ts
+++ b/x-pack/plugins/enterprise_search/public/applications/enterprise_search_content/utils/connector_status_helpers.ts
@@ -6,17 +6,16 @@
  */
 
 import { i18n } from '@kbn/i18n';
-import { ConnectorStatus } from '@kbn/search-connectors';
+import { Connector, ConnectorStatus, SyncStatus } from '@kbn/search-connectors';
 
 const incompleteText = i18n.translate(
   'xpack.enterpriseSearch.content.searchIndices.ingestionStatus.incomplete.label',
   { defaultMessage: 'Incomplete' }
 );
 
-export function connectorStatusToText(
-  connectorStatus: ConnectorStatus,
-  hasIndexName: boolean
-): string {
+export function connectorStatusToText(connector: Connector): string {
+  const hasIndexName = !!connector.index_name;
+  const connectorStatus = connector.status;
   if (
     connectorStatus === ConnectorStatus.CREATED ||
     connectorStatus === ConnectorStatus.NEEDS_CONFIGURATION
@@ -26,6 +25,16 @@ export function connectorStatusToText(
       { defaultMessage: 'Needs Configuration' }
     );
   }
+  if (
+    connector.error === SyncStatus.ERROR ||
+    connector.last_sync_error !== null ||
+    connector.last_access_control_sync_error !== null
+  ) {
+    return i18n.translate(
+      'xpack.enterpriseSearch.content.searchIndices.connectorStatus.syncFailure.label',
+      { defaultMessage: 'Sync Failure' }
+    );
+  }
   if (connectorStatus === ConnectorStatus.ERROR) {
     return i18n.translate(
       'xpack.enterpriseSearch.content.searchIndices.connectorStatus.connectorFailure.label',
@@ -51,18 +60,22 @@ export function connectorStatusToText(
   return incompleteText;
 }
 
-export function connectorStatusToColor(
-  connectorStatus: ConnectorStatus,
-  hasIndexName: boolean
-): 'warning' | 'danger' | 'success' {
+export function connectorStatusToColor(connector: Connector): 'warning' | 'danger' | 'success' {
+  const hasIndexName = !!connector.index_name;
+  const connectorStatus = connector.status;
   if (!hasIndexName) {
     return 'warning';
   }
+  if (
+    connectorStatus === ConnectorStatus.ERROR ||
+    connector.error === SyncStatus.ERROR ||
+    connector.last_sync_error !== null ||
+    connector.last_access_control_sync_error !== null
+  ) {
+    return 'danger';
+  }
   if (connectorStatus === ConnectorStatus.CONNECTED) {
     return 'success';
   }
-  if (connectorStatus === ConnectorStatus.ERROR) {
-    return 'danger';
-  }
   return 'warning';
 }
diff --git a/x-pack/plugins/enterprise_search/server/utils/get_sync_jobs_queries.ts b/x-pack/plugins/enterprise_search/server/utils/get_sync_jobs_queries.ts
index 5fe2e9b17eff730..ff6eeee4db472f5 100644
--- a/x-pack/plugins/enterprise_search/server/utils/get_sync_jobs_queries.ts
+++ b/x-pack/plugins/enterprise_search/server/utils/get_sync_jobs_queries.ts
@@ -331,24 +331,18 @@ export const getIncompleteCountQuery = (isCrawler?: boolean) => {
   }
   return {
     bool: {
-      should: [
-        {
-          bool: {
-            must_not: {
-              terms: {
-                status: [ConnectorStatus.CONNECTED, ConnectorStatus.ERROR],
-              },
-            },
-          },
+      must_not: {
+        terms: {
+          status: [ConnectorStatus.CONNECTED, ConnectorStatus.ERROR],
         },
-        {
-          range: {
-            last_seen: {
-              lt: moment().subtract(30, 'minutes').toISOString(),
-            },
+      },
+      must: {
+        range: {
+          last_seen: {
+            lt: moment().subtract(30, 'minutes').toISOString(),
           },
         },
-      ],
+      },
       filter: [
         {
           bool: {