diff --git a/x-pack/plugins/fleet/common/types/models/agent.ts b/x-pack/plugins/fleet/common/types/models/agent.ts
index b3beb3d6cdec7..fb7c513762784 100644
--- a/x-pack/plugins/fleet/common/types/models/agent.ts
+++ b/x-pack/plugins/fleet/common/types/models/agent.ts
@@ -161,7 +161,7 @@ export interface AgentDiagnostics {
   name: string;
   createTime: string;
   filePath: string;
-  status: 'READY' | 'AWAITING_UPLOAD' | 'DELETED' | 'IN_PROGRESS';
+  status: 'READY' | 'AWAITING_UPLOAD' | 'DELETED' | 'IN_PROGRESS' | 'FAILED';
   actionId: string;
 }
 
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 72b0bd18a555d..b0a588a1d12c4 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
@@ -132,7 +132,7 @@ export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps>
           </EuiText>
         ) : (
           <EuiText color="subdued">
-            <EuiToolTip content={`File status: ${currentItem?.status}`}>
+            <EuiToolTip content={`Diagnostics status: ${currentItem?.status}`}>
               <EuiIcon type="alert" color="red" />
             </EuiToolTip>
             &nbsp;
diff --git a/x-pack/plugins/fleet/server/services/agents/uploads.ts b/x-pack/plugins/fleet/server/services/agents/uploads.ts
index a73525d7efc4a..6085ef1e5b801 100644
--- a/x-pack/plugins/fleet/server/services/agents/uploads.ts
+++ b/x-pack/plugins/fleet/server/services/agents/uploads.ts
@@ -72,7 +72,7 @@ export async function getAgentUploads(
     const result = {
       actionId: action.actionId,
       id: file?.id ?? action.actionId,
-      status: file?.Status ?? 'IN_PROGRESS',
+      status: file?.Status ?? (action.error ? 'FAILED' : 'IN_PROGRESS'),
       name: fileName,
       createTime: action.timestamp!,
       filePath,
@@ -86,7 +86,7 @@ export async function getAgentUploads(
 async function _getRequestDiagnosticsActions(
   esClient: ElasticsearchClient,
   agentId: string
-): Promise<Array<{ actionId: string; timestamp?: string; fileId?: string }>> {
+): Promise<Array<{ actionId: string; timestamp?: string; fileId?: string; error?: string }>> {
   const agentActionRes = await esClient.search<any>({
     index: AGENT_ACTIONS_INDEX,
     ignore_unavailable: true,
@@ -144,6 +144,7 @@ async function _getRequestDiagnosticsActions(
       actionId: hit._source?.action_id as string,
       timestamp: hit._source?.['@timestamp'],
       fileId: hit._source?.data?.file_id as string,
+      error: hit._source?.error,
     }));
     return agentActions.map((action) => {
       const actionResult = actionResults.find((result) => result.actionId === action.actionId);
@@ -151,6 +152,7 @@ async function _getRequestDiagnosticsActions(
         actionId: action.actionId,
         timestamp: actionResult?.timestamp ?? action.timestamp,
         fileId: actionResult?.fileId,
+        error: actionResult?.error,
       };
     });
   } catch (err) {