diff --git a/x-pack/plugins/fleet/common/types/models/agent.ts b/x-pack/plugins/fleet/common/types/models/agent.ts
index fb7c51376278..e530ca152add 100644
--- a/x-pack/plugins/fleet/common/types/models/agent.ts
+++ b/x-pack/plugins/fleet/common/types/models/agent.ts
@@ -163,6 +163,7 @@ export interface AgentDiagnostics {
   filePath: string;
   status: 'READY' | 'AWAITING_UPLOAD' | 'DELETED' | 'IN_PROGRESS' | 'FAILED';
   actionId: string;
+  error?: string;
 }
 
 // Generated from FleetServer schema.json
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/agent_diagnostics/index.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/agent_diagnostics/index.tsx
index b0a588a1d12c..2c38fdfba536 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/agent_diagnostics/index.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/agent_diagnostics/index.tsx
@@ -37,6 +37,10 @@ const FlexStartEuiFlexItem = styled(EuiFlexItem)`
   align-self: flex-start;
 `;
 
+const MarginedIcon = styled(EuiIcon)`
+  margin-right: 7px;
+`;
+
 export interface AgentDiagnosticsProps {
   agent: Agent;
 }
@@ -48,6 +52,7 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
   const [isLoading, setIsLoading] = useState(true);
   const [diagnosticsEntries, setDiagnosticEntries] = useState<AgentDiagnostics[]>([]);
   const [prevDiagnosticsEntries, setPrevDiagnosticEntries] = useState<AgentDiagnostics[]>([]);
+  const [loadInterval, setLoadInterval] = useState(10000);
 
   const loadData = useCallback(async () => {
     try {
@@ -59,8 +64,20 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
       if (!uploadsResponse.data) {
         throw new Error('No data');
       }
-      setDiagnosticEntries(uploadsResponse.data.items);
+      const entries = uploadsResponse.data.items;
+      setDiagnosticEntries(entries);
       setIsLoading(false);
+
+      // query faster if an action is in progress, for quicker feedback
+      if (
+        entries.some(
+          (entry) => entry.status === 'IN_PROGRESS' || entry.status === 'AWAITING_UPLOAD'
+        )
+      ) {
+        setLoadInterval(3000);
+      } else {
+        setLoadInterval(10000);
+      }
     } catch (err) {
       notifications.toasts.addError(err, {
         title: i18n.translate(
@@ -71,13 +88,13 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
         ),
       });
     }
-  }, [agent.id, notifications.toasts]);
+  }, [agent.id, notifications.toasts, setLoadInterval]);
 
   useEffect(() => {
     loadData();
     const interval: ReturnType<typeof setInterval> | null = setInterval(async () => {
       loadData();
-    }, 10000);
+    }, loadInterval);
 
     const cleanup = () => {
       if (interval) {
@@ -86,7 +103,7 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
     };
 
     return cleanup;
-  }, [loadData]);
+  }, [loadData, loadInterval]);
 
   useEffect(() => {
     setPrevDiagnosticEntries(diagnosticsEntries);
@@ -112,6 +129,9 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
     }
   }, [prevDiagnosticsEntries, diagnosticsEntries, notifications.toasts]);
 
+  const errorIcon = <MarginedIcon type="alert" color="red" />;
+  const getErrorMessage = (error?: string) => (error ? `Error: ${error}` : '');
+
   const columns: Array<EuiTableFieldDataColumnType<AgentDiagnostics>> = [
     {
       field: 'id',
@@ -123,21 +143,32 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
             <EuiIcon type="download" /> &nbsp; {currentItem?.name}
           </EuiLink>
         ) : currentItem?.status === 'IN_PROGRESS' || currentItem?.status === 'AWAITING_UPLOAD' ? (
-          <EuiText color="subdued">
+          <EuiLink color="subdued" disabled>
             <EuiLoadingSpinner /> &nbsp;
             <FormattedMessage
               id="xpack.fleet.requestDiagnostics.generatingText"
               defaultMessage="Generating diagnostics file..."
             />
-          </EuiText>
+          </EuiLink>
         ) : (
-          <EuiText color="subdued">
-            <EuiToolTip content={`Diagnostics status: ${currentItem?.status}`}>
-              <EuiIcon type="alert" color="red" />
-            </EuiToolTip>
+          <EuiLink color="subdued" disabled>
+            {currentItem?.status ? (
+              <EuiToolTip
+                content={
+                  <>
+                    <p>Diagnostics status: {currentItem?.status}</p>
+                    <p>{getErrorMessage(currentItem?.error)}</p>
+                  </>
+                }
+              >
+                {errorIcon}
+              </EuiToolTip>
+            ) : (
+              errorIcon
+            )}
             &nbsp;
             {currentItem?.name}
-          </EuiText>
+          </EuiLink>
         );
       },
     },
@@ -149,7 +180,7 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
         const currentItem = diagnosticsEntries.find((item) => item.id === id);
         return (
           <EuiText color={currentItem?.status === 'READY' ? 'default' : 'subdued'}>
-            {formatDate(currentItem?.createTime, 'll')}
+            {formatDate(currentItem?.createTime, 'lll')}
           </EuiText>
         );
       },
@@ -171,6 +202,7 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
         }
       );
       notifications.toasts.addSuccess(successMessage);
+      loadData();
     } catch (error) {
       setIsSubmitting(false);
       notifications.toasts.addError(error, {
diff --git a/x-pack/plugins/fleet/server/services/agents/uploads.ts b/x-pack/plugins/fleet/server/services/agents/uploads.ts
index 7402eedc840e..3683b9b0d90a 100644
--- a/x-pack/plugins/fleet/server/services/agents/uploads.ts
+++ b/x-pack/plugins/fleet/server/services/agents/uploads.ts
@@ -31,21 +31,24 @@ export async function getAgentUploads(
   esClient: ElasticsearchClient,
   agentId: string
 ): Promise<AgentDiagnostics[]> {
-  const getFile = async (fileId: string) => {
-    if (!fileId) return;
+  const getFile = async (actionId: string) => {
     try {
       const fileResponse = await esClient.search({
         index: FILE_STORAGE_METADATA_AGENT_INDEX,
         query: {
           bool: {
             filter: {
-              term: { upload_id: fileId },
+              bool: {
+                must: [{ term: { agent_id: agentId } }, { term: { action_id: actionId } }],
+              },
             },
           },
         },
       });
-      if (fileResponse.hits.total === 0) {
-        appContextService.getLogger().debug(`No matches for upload_id ${fileId}`);
+      if (fileResponse.hits.hits.length === 0) {
+        appContextService
+          .getLogger()
+          .debug(`No matches for action_id ${actionId} and agent_id ${agentId}`);
         return;
       }
       return {
@@ -64,10 +67,14 @@ export async function getAgentUploads(
 
   const actions = await _getRequestDiagnosticsActions(esClient, agentId);
 
-  const results = [];
+  const results: AgentDiagnostics[] = [];
   for (const action of actions) {
-    const file = action.fileId ? await getFile(action.fileId) : undefined;
-    const fileName = file?.name ?? `${moment(action.timestamp!).format('YYYY-MM-DD HH:mm:ss')}.zip`;
+    const file = await getFile(action.actionId);
+    const fileName =
+      file?.name ??
+      `elastic-agent-diagnostics-${moment
+        .utc(action.timestamp!)
+        .format('YYYY-MM-DDTHH-mm-ss')}Z-00.zip`;
     const filePath = file ? agentRouteService.getAgentFileDownloadLink(file.id, file.name) : '';
     const result = {
       actionId: action.actionId,
@@ -76,6 +83,7 @@ export async function getAgentUploads(
       name: fileName,
       createTime: action.timestamp!,
       filePath,
+      error: action.error,
     };
     results.push(result);
   }
@@ -91,6 +99,7 @@ async function _getRequestDiagnosticsActions(
     index: AGENT_ACTIONS_INDEX,
     ignore_unavailable: true,
     size: SO_SEARCH_LIMIT,
+    sort: { '@timestamp': 'desc' },
     query: {
       bool: {
         must: [
@@ -150,7 +159,7 @@ async function _getRequestDiagnosticsActions(
       const actionResult = actionResults.find((result) => result.actionId === action.actionId);
       return {
         actionId: action.actionId,
-        timestamp: actionResult?.timestamp ?? action.timestamp,
+        timestamp: action.timestamp,
         fileId: actionResult?.fileId,
         error: actionResult?.error,
       };
diff --git a/x-pack/test/fleet_api_integration/apis/agents/uploads.ts b/x-pack/test/fleet_api_integration/apis/agents/uploads.ts
index c0f32104d24f..6f548d3d955d 100644
--- a/x-pack/test/fleet_api_integration/apis/agents/uploads.ts
+++ b/x-pack/test/fleet_api_integration/apis/agents/uploads.ts
@@ -68,6 +68,8 @@ export default function (providerContext: FtrProviderContext) {
           doc_as_upsert: true,
           doc: {
             upload_id: 'file1',
+            action_id: 'action1',
+            agent_id: 'agent1',
             file: {
               ChunkSize: 4194304,
               extension: 'zip',
@@ -96,7 +98,7 @@ export default function (providerContext: FtrProviderContext) {
 
       expect(body.items[0]).to.eql({
         actionId: 'action1',
-        createTime: '2022-10-07T12:00:00.000Z',
+        createTime: '2022-10-07T11:00:00.000Z',
         filePath:
           '/api/fleet/agents/files/file1/elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip',
         id: 'file1',
@@ -130,5 +132,49 @@ export default function (providerContext: FtrProviderContext) {
         'attachment; filename="elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip"'
       );
     });
+
+    it('should return failed status with error message', async () => {
+      await esClient.create({
+        index: AGENT_ACTIONS_INDEX,
+        id: new Date().toISOString(),
+        refresh: true,
+        body: {
+          type: 'REQUEST_DIAGNOSTICS',
+          action_id: 'action2',
+          agents: ['agent2'],
+          '@timestamp': '2022-10-07T11:00:00.000Z',
+        },
+      });
+      await esClient.create(
+        {
+          index: AGENT_ACTIONS_RESULTS_INDEX,
+          id: new Date().toISOString(),
+          refresh: true,
+          body: {
+            action_id: 'action2',
+            agent_id: 'agent2',
+            '@timestamp': '2022-10-07T12:00:00.000Z',
+            data: {},
+            error: 'rate limit exceeded',
+          },
+        },
+        ES_INDEX_OPTIONS
+      );
+
+      const { body } = await supertest
+        .get(`/api/fleet/agents/agent2/uploads`)
+        .set('kbn-xsrf', 'xxx')
+        .expect(200);
+
+      expect(body.items[0]).to.eql({
+        actionId: 'action2',
+        createTime: '2022-10-07T11:00:00.000Z',
+        filePath: '',
+        id: 'action2',
+        name: 'elastic-agent-diagnostics-2022-10-07T11-00-00Z-00.zip',
+        status: 'FAILED',
+        error: 'rate limit exceeded',
+      });
+    });
   });
 }