diff --git a/x-pack/plugins/fleet/common/constants/routes.ts b/x-pack/plugins/fleet/common/constants/routes.ts
index d48e07223cdf9..8f08c41a7565f 100644
--- a/x-pack/plugins/fleet/common/constants/routes.ts
+++ b/x-pack/plugins/fleet/common/constants/routes.ts
@@ -127,6 +127,8 @@ export const AGENT_API_ROUTES = {
   BULK_UNENROLL_PATTERN: `${API_ROOT}/agents/bulk_unenroll`,
   REASSIGN_PATTERN: `${API_ROOT}/agents/{agentId}/reassign`,
   BULK_REASSIGN_PATTERN: `${API_ROOT}/agents/bulk_reassign`,
+  REQUEST_DIAGNOSTICS_PATTERN: `${API_ROOT}/agents/{agentId}/request_diagnostics`,
+  BULK_REQUEST_DIAGNOSTICS_PATTERN: `${API_ROOT}/agents/bulk_request_diagnostics`,
   AVAILABLE_VERSIONS_PATTERN: `${API_ROOT}/agents/available_versions`,
   STATUS_PATTERN: `${API_ROOT}/agent_status`,
   DATA_PATTERN: `${API_ROOT}/agent_status/data`,
@@ -137,6 +139,8 @@ export const AGENT_API_ROUTES = {
   CURRENT_UPGRADES_PATTERN: `${API_ROOT}/agents/current_upgrades`,
   ACTION_STATUS_PATTERN: `${API_ROOT}/agents/action_status`,
   LIST_TAGS_PATTERN: `${API_ROOT}/agents/tags`,
+  LIST_UPLOADS_PATTERN: `${API_ROOT}/agents/{agentId}/uploads`,
+  GET_UPLOAD_FILE_PATTERN: `${API_ROOT}/agents/files/{fileId}/{fileName}`,
 };
 
 export const ENROLLMENT_API_KEY_ROUTES = {
diff --git a/x-pack/plugins/fleet/common/experimental_features.ts b/x-pack/plugins/fleet/common/experimental_features.ts
index 8926a1092fca2..2c55ce4a2a08e 100644
--- a/x-pack/plugins/fleet/common/experimental_features.ts
+++ b/x-pack/plugins/fleet/common/experimental_features.ts
@@ -15,6 +15,7 @@ export const allowedExperimentalValues = Object.freeze({
   createPackagePolicyMultiPageLayout: true,
   packageVerification: true,
   showDevtoolsRequest: true,
+  showRequestDiagnostics: false,
 });
 
 type ExperimentalConfigKeys = Array<keyof ExperimentalFeatures>;
diff --git a/x-pack/plugins/fleet/common/services/routes.ts b/x-pack/plugins/fleet/common/services/routes.ts
index 4c8f053b56cf9..80b9e35430066 100644
--- a/x-pack/plugins/fleet/common/services/routes.ts
+++ b/x-pack/plugins/fleet/common/services/routes.ts
@@ -206,6 +206,16 @@ export const agentRouteService = {
     AGENT_API_ROUTES.ACTIONS_PATTERN.replace('{agentId}', agentId),
   getListTagsPath: () => AGENT_API_ROUTES.LIST_TAGS_PATTERN,
   getAvailableVersionsPath: () => AGENT_API_ROUTES.AVAILABLE_VERSIONS_PATTERN,
+  getRequestDiagnosticsPath: (agentId: string) =>
+    AGENT_API_ROUTES.REQUEST_DIAGNOSTICS_PATTERN.replace('{agentId}', agentId),
+  getBulkRequestDiagnosticsPath: () => AGENT_API_ROUTES.BULK_REQUEST_DIAGNOSTICS_PATTERN,
+  getListAgentUploads: (agentId: string) =>
+    AGENT_API_ROUTES.LIST_UPLOADS_PATTERN.replace('{agentId}', agentId),
+  getAgentFileDownloadLink: (fileId: string, fileName: string) =>
+    AGENT_API_ROUTES.GET_UPLOAD_FILE_PATTERN.replace('{fileId}', fileId).replace(
+      '{fileName}',
+      fileName
+    ),
 };
 
 export const outputRoutesService = {
diff --git a/x-pack/plugins/fleet/common/types/models/agent.ts b/x-pack/plugins/fleet/common/types/models/agent.ts
index 9e47451aa02bb..e272c889a83b6 100644
--- a/x-pack/plugins/fleet/common/types/models/agent.ts
+++ b/x-pack/plugins/fleet/common/types/models/agent.ts
@@ -37,7 +37,8 @@ export type AgentActionType =
   | 'POLICY_REASSIGN'
   | 'CANCEL'
   | 'FORCE_UNENROLL'
-  | 'UPDATE_TAGS';
+  | 'UPDATE_TAGS'
+  | 'REQUEST_DIAGNOSTICS';
 
 type FleetServerAgentComponentStatusTuple = typeof FleetServerAgentComponentStatuses;
 export type FleetServerAgentComponentStatus = FleetServerAgentComponentStatusTuple[number];
@@ -142,6 +143,15 @@ export interface ActionStatus {
   creationTime: string;
 }
 
+export interface AgentDiagnostics {
+  id: string;
+  name: string;
+  createTime: string;
+  filePath: string;
+  status: 'READY' | 'AWAITING_UPLOAD' | 'DELETED' | 'IN_PROGRESS';
+  actionId: string;
+}
+
 // Generated from FleetServer schema.json
 export interface FleetServerAgentComponentUnit {
   id: string;
diff --git a/x-pack/plugins/fleet/common/types/rest_spec/agent.ts b/x-pack/plugins/fleet/common/types/rest_spec/agent.ts
index 9a18613d95834..8af5ee9abe1e3 100644
--- a/x-pack/plugins/fleet/common/types/rest_spec/agent.ts
+++ b/x-pack/plugins/fleet/common/types/rest_spec/agent.ts
@@ -7,7 +7,14 @@
 
 import type { SearchHit } from '@kbn/es-types';
 
-import type { Agent, AgentAction, ActionStatus, CurrentUpgrade, NewAgentAction } from '../models';
+import type {
+  Agent,
+  AgentAction,
+  ActionStatus,
+  CurrentUpgrade,
+  NewAgentAction,
+  AgentDiagnostics,
+} from '../models';
 
 import type { ListResult, ListWithKuery } from './common';
 
@@ -38,6 +45,10 @@ export interface GetOneAgentResponse {
   item: Agent;
 }
 
+export interface GetAgentUploadsResponse {
+  items: AgentDiagnostics[];
+}
+
 export interface PostNewAgentActionRequest {
   body: {
     action: Omit<NewAgentAction, 'agents'>;
@@ -121,6 +132,16 @@ export interface PostBulkAgentReassignRequest {
   };
 }
 
+export type PostRequestDiagnosticsResponse = BulkAgentAction;
+export type PostBulkRequestDiagnosticsResponse = BulkAgentAction;
+
+export interface PostRequestBulkDiagnosticsRequest {
+  body: {
+    agents: string[] | string;
+    batchSize?: number;
+  };
+}
+
 export type PostBulkAgentReassignResponse = BulkAgentAction;
 
 export type PostBulkUpdateAgentTagsResponse = BulkAgentAction;
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/actions_menu.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/actions_menu.tsx
index c57347894003d..b52a0401b8650 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/actions_menu.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/actions_menu.tsx
@@ -19,6 +19,8 @@ import {
 } from '../../components';
 import { useAgentRefresh } from '../hooks';
 import { isAgentUpgradeable, policyHasFleetServer } from '../../../../services';
+import { AgentRequestDiagnosticsModal } from '../../components/agent_request_diagnostics_modal';
+import { ExperimentalFeaturesService } from '../../../../services';
 
 export const AgentDetailsActionMenu: React.FunctionComponent<{
   agent: Agent;
@@ -32,9 +34,11 @@ export const AgentDetailsActionMenu: React.FunctionComponent<{
   const [isReassignFlyoutOpen, setIsReassignFlyoutOpen] = useState(assignFlyoutOpenByDefault);
   const [isUnenrollModalOpen, setIsUnenrollModalOpen] = useState(false);
   const [isUpgradeModalOpen, setIsUpgradeModalOpen] = useState(false);
+  const [isRequestDiagnosticsModalOpen, setIsRequestDiagnosticsModalOpen] = useState(false);
   const isUnenrolling = agent.status === 'unenrolling';
 
   const hasFleetServer = agentPolicy && policyHasFleetServer(agentPolicy);
+  const { showRequestDiagnostics } = ExperimentalFeaturesService.get();
 
   const onClose = useMemo(() => {
     if (onCancelReassign) {
@@ -44,6 +48,70 @@ export const AgentDetailsActionMenu: React.FunctionComponent<{
     }
   }, [onCancelReassign, setIsReassignFlyoutOpen]);
 
+  const menuItems = [
+    <EuiContextMenuItem
+      icon="pencil"
+      onClick={() => {
+        setIsReassignFlyoutOpen(true);
+      }}
+      disabled={!agent.active}
+      key="reassignPolicy"
+    >
+      <FormattedMessage
+        id="xpack.fleet.agentList.reassignActionText"
+        defaultMessage="Assign to new policy"
+      />
+    </EuiContextMenuItem>,
+    <EuiContextMenuItem
+      icon="trash"
+      disabled={!hasFleetAllPrivileges || !agent.active}
+      onClick={() => {
+        setIsUnenrollModalOpen(true);
+      }}
+    >
+      {isUnenrolling ? (
+        <FormattedMessage
+          id="xpack.fleet.agentList.forceUnenrollOneButton"
+          defaultMessage="Force unenroll"
+        />
+      ) : (
+        <FormattedMessage
+          id="xpack.fleet.agentList.unenrollOneButton"
+          defaultMessage="Unenroll agent"
+        />
+      )}
+    </EuiContextMenuItem>,
+    <EuiContextMenuItem
+      icon="refresh"
+      disabled={!isAgentUpgradeable(agent, kibanaVersion)}
+      onClick={() => {
+        setIsUpgradeModalOpen(true);
+      }}
+    >
+      <FormattedMessage
+        id="xpack.fleet.agentList.upgradeOneButton"
+        defaultMessage="Upgrade agent"
+      />
+    </EuiContextMenuItem>,
+  ];
+
+  if (showRequestDiagnostics) {
+    menuItems.push(
+      <EuiContextMenuItem
+        icon="download"
+        disabled={!hasFleetAllPrivileges}
+        onClick={() => {
+          setIsRequestDiagnosticsModalOpen(true);
+        }}
+      >
+        <FormattedMessage
+          id="xpack.fleet.agentList.diagnosticsOneButton"
+          defaultMessage="Request diagnostics .zip"
+        />
+      </EuiContextMenuItem>
+    );
+  }
+
   return (
     <>
       {isReassignFlyoutOpen && (
@@ -77,6 +145,17 @@ export const AgentDetailsActionMenu: React.FunctionComponent<{
           />
         </EuiPortal>
       )}
+      {isRequestDiagnosticsModalOpen && (
+        <EuiPortal>
+          <AgentRequestDiagnosticsModal
+            agents={[agent]}
+            agentCount={1}
+            onClose={() => {
+              setIsRequestDiagnosticsModalOpen(false);
+            }}
+          />
+        </EuiPortal>
+      )}
       <ContextMenuActions
         button={{
           props: { iconType: 'arrowDown', iconSide: 'right', color: 'primary' },
@@ -87,52 +166,7 @@ export const AgentDetailsActionMenu: React.FunctionComponent<{
             />
           ),
         }}
-        items={[
-          <EuiContextMenuItem
-            icon="pencil"
-            onClick={() => {
-              setIsReassignFlyoutOpen(true);
-            }}
-            disabled={!agent.active}
-            key="reassignPolicy"
-          >
-            <FormattedMessage
-              id="xpack.fleet.agentList.reassignActionText"
-              defaultMessage="Assign to new policy"
-            />
-          </EuiContextMenuItem>,
-          <EuiContextMenuItem
-            icon="trash"
-            disabled={!hasFleetAllPrivileges || !agent.active}
-            onClick={() => {
-              setIsUnenrollModalOpen(true);
-            }}
-          >
-            {isUnenrolling ? (
-              <FormattedMessage
-                id="xpack.fleet.agentList.forceUnenrollOneButton"
-                defaultMessage="Force unenroll"
-              />
-            ) : (
-              <FormattedMessage
-                id="xpack.fleet.agentList.unenrollOneButton"
-                defaultMessage="Unenroll agent"
-              />
-            )}
-          </EuiContextMenuItem>,
-          <EuiContextMenuItem
-            icon="refresh"
-            disabled={!isAgentUpgradeable(agent, kibanaVersion)}
-            onClick={() => {
-              setIsUpgradeModalOpen(true);
-            }}
-          >
-            <FormattedMessage
-              id="xpack.fleet.agentList.upgradeOneButton"
-              defaultMessage="Upgrade agent"
-            />
-          </EuiContextMenuItem>,
-        ]}
+        items={menuItems}
       />
     </>
   );
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
new file mode 100644
index 0000000000000..7f9bc76799ed3
--- /dev/null
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/agent_diagnostics/index.tsx
@@ -0,0 +1,218 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import type { EuiTableFieldDataColumnType } from '@elastic/eui';
+import {
+  EuiBasicTable,
+  EuiButton,
+  EuiCallOut,
+  EuiFlexGroup,
+  EuiFlexItem,
+  EuiIcon,
+  EuiLink,
+  EuiLoadingContent,
+  EuiLoadingSpinner,
+  EuiText,
+  formatDate,
+} from '@elastic/eui';
+import React, { useCallback, useEffect, useState } from 'react';
+import styled from 'styled-components';
+import { FormattedMessage } from '@kbn/i18n-react';
+import { i18n } from '@kbn/i18n';
+
+import {
+  sendGetAgentUploads,
+  sendPostRequestDiagnostics,
+  useLink,
+  useStartServices,
+} from '../../../../../hooks';
+import type { AgentDiagnostics, Agent } from '../../../../../../../../common/types/models';
+
+const FlexStartEuiFlexItem = styled(EuiFlexItem)`
+  align-self: flex-start;
+`;
+
+export interface AgentDiagnosticsProps {
+  agent: Agent;
+}
+
+export const AgentDiagnosticsTab: React.FunctionComponent<AgentDiagnosticsProps> = ({ agent }) => {
+  const { notifications } = useStartServices();
+  const { getAbsolutePath } = useLink();
+  const [isSubmitting, setIsSubmitting] = useState(false);
+  const [isLoading, setIsLoading] = useState(true);
+  const [diagnosticsEntries, setDiagnosticEntries] = useState<AgentDiagnostics[]>([]);
+  const [prevDiagnosticsEntries, setPrevDiagnosticEntries] = useState<AgentDiagnostics[]>([]);
+
+  const loadData = useCallback(async () => {
+    try {
+      const uploadsResponse = await sendGetAgentUploads(agent.id);
+      const error = uploadsResponse.error;
+      if (error) {
+        throw error;
+      }
+      if (!uploadsResponse.data) {
+        throw new Error('No data');
+      }
+      setDiagnosticEntries(uploadsResponse.data.items);
+      setIsLoading(false);
+    } catch (err) {
+      notifications.toasts.addError(err, {
+        title: i18n.translate(
+          'xpack.fleet.requestDiagnostics.errorLoadingUploadsNotificationTitle',
+          {
+            defaultMessage: 'Error loading diagnostics uploads',
+          }
+        ),
+      });
+    }
+  }, [agent.id, notifications.toasts]);
+
+  useEffect(() => {
+    loadData();
+    const interval: ReturnType<typeof setInterval> | null = setInterval(async () => {
+      loadData();
+    }, 10000);
+
+    const cleanup = () => {
+      if (interval) {
+        clearInterval(interval);
+      }
+    };
+
+    return cleanup;
+  }, [loadData]);
+
+  useEffect(() => {
+    setPrevDiagnosticEntries(diagnosticsEntries);
+    if (prevDiagnosticsEntries.length > 0) {
+      diagnosticsEntries
+        .filter((newEntry) => {
+          const oldEntry = prevDiagnosticsEntries.find((entry) => entry.id === newEntry.id);
+          return newEntry.status === 'READY' && (!oldEntry || oldEntry?.status !== 'READY');
+        })
+        .forEach((entry) => {
+          notifications.toasts.addSuccess(
+            {
+              title: i18n.translate('xpack.fleet.requestDiagnostics.readyNotificationTitle', {
+                defaultMessage: 'Agent diagnostics {name} ready',
+                values: {
+                  name: entry.name,
+                },
+              }),
+            },
+            { toastLifeTimeMs: 5000 }
+          );
+        });
+    }
+  }, [prevDiagnosticsEntries, diagnosticsEntries, notifications.toasts]);
+
+  const columns: Array<EuiTableFieldDataColumnType<AgentDiagnostics>> = [
+    {
+      field: 'id',
+      name: 'File',
+      render: (id: string) => {
+        const currentItem = diagnosticsEntries.find((item) => item.id === id);
+        return currentItem?.status === 'READY' ? (
+          <EuiLink href={getAbsolutePath(currentItem?.filePath)} download target="_blank">
+            <EuiIcon type="download" /> &nbsp; {currentItem?.name}
+          </EuiLink>
+        ) : currentItem?.status === 'IN_PROGRESS' || currentItem?.status === 'AWAITING_UPLOAD' ? (
+          <EuiText color="subdued">
+            <EuiLoadingSpinner /> &nbsp;
+            <FormattedMessage
+              id="xpack.fleet.requestDiagnostics.generatingText"
+              defaultMessage="Generating diagnostics file..."
+            />
+          </EuiText>
+        ) : (
+          <EuiText color="subdued">
+            <EuiIcon type="alert" color="red" /> &nbsp;
+            {currentItem?.name}
+          </EuiText>
+        );
+      },
+    },
+    {
+      field: 'id',
+      name: 'Date',
+      dataType: 'date',
+      render: (id: string) => {
+        const currentItem = diagnosticsEntries.find((item) => item.id === id);
+        return (
+          <EuiText color={currentItem?.status === 'READY' ? 'default' : 'subdued'}>
+            {formatDate(currentItem?.createTime, 'll')}
+          </EuiText>
+        );
+      },
+    },
+  ];
+
+  async function onSubmit() {
+    try {
+      setIsSubmitting(true);
+      const { error } = await sendPostRequestDiagnostics(agent.id);
+      if (error) {
+        throw error;
+      }
+      setIsSubmitting(false);
+      const successMessage = i18n.translate(
+        'xpack.fleet.requestDiagnostics.successSingleNotificationTitle',
+        {
+          defaultMessage: 'Request diagnostics submitted',
+        }
+      );
+      notifications.toasts.addSuccess(successMessage);
+    } catch (error) {
+      setIsSubmitting(false);
+      notifications.toasts.addError(error, {
+        title: i18n.translate('xpack.fleet.requestDiagnostics.fatalErrorNotificationTitle', {
+          defaultMessage:
+            'Error requesting diagnostics {count, plural, one {agent} other {agents}}',
+          values: { count: 1 },
+        }),
+      });
+    }
+  }
+
+  return (
+    <EuiFlexGroup direction="column" gutterSize="l">
+      <EuiFlexItem>
+        <EuiCallOut
+          iconType="alert"
+          color="warning"
+          title={
+            <FormattedMessage
+              id="xpack.fleet.fleetServerSetup.calloutTitle"
+              defaultMessage="Agent diagnostics"
+            />
+          }
+        >
+          <FormattedMessage
+            id="xpack.fleet.requestDiagnostics.calloutText"
+            defaultMessage="Diagnostics files are stored in Elasticsearch, and as such can incur storage costs. Fleet will automatically remove old diagnostics files after 30 days."
+          />
+        </EuiCallOut>
+      </EuiFlexItem>
+      <FlexStartEuiFlexItem>
+        <EuiButton fill size="m" onClick={onSubmit} disabled={isSubmitting}>
+          <FormattedMessage
+            id="xpack.fleet.agentList.diagnosticsOneButton"
+            defaultMessage="Request diagnostics .zip"
+          />
+        </EuiButton>
+      </FlexStartEuiFlexItem>
+      <EuiFlexItem>
+        {isLoading ? (
+          <EuiLoadingContent lines={3} />
+        ) : (
+          <EuiBasicTable<AgentDiagnostics> items={diagnosticsEntries} columns={columns} />
+        )}
+      </EuiFlexItem>
+    </EuiFlexGroup>
+  );
+};
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/index.ts b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/index.ts
index 5a806d52d3af9..858bb31033716 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/index.ts
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/components/index.ts
@@ -9,3 +9,4 @@ export { AgentLogs } from './agent_logs';
 export { AgentDetailsActionMenu } from './actions_menu';
 export { AgentDetailsContent } from './agent_details';
 export { AgentDashboardLink } from './agent_dashboard_link';
+export { AgentDiagnosticsTab } from './agent_diagnostics';
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/index.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/index.tsx
index 5654f4a18d1d3..b2e9bd76194e4 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/index.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_details_page/index.tsx
@@ -25,12 +25,15 @@ import {
 } from '../../../hooks';
 import { WithHeaderLayout } from '../../../layouts';
 
+import { ExperimentalFeaturesService } from '../../../services';
+
 import { AgentRefreshContext } from './hooks';
 import {
   AgentLogs,
   AgentDetailsActionMenu,
   AgentDetailsContent,
   AgentDashboardLink,
+  AgentDiagnosticsTab,
 } from './components';
 
 export const AgentDetailsPage: React.FunctionComponent = () => {
@@ -65,6 +68,7 @@ export const AgentDetailsPage: React.FunctionComponent = () => {
       navigateToApp(routeState.onDoneNavigateTo[0], routeState.onDoneNavigateTo[1]);
     }
   }, [routeState, navigateToApp]);
+  const { showRequestDiagnostics } = ExperimentalFeaturesService.get();
 
   const host = agentData?.item?.local_metadata?.host;
 
@@ -134,7 +138,7 @@ export const AgentDetailsPage: React.FunctionComponent = () => {
   );
 
   const headerTabs = useMemo(() => {
-    return [
+    const tabs = [
       {
         id: 'details',
         name: i18n.translate('xpack.fleet.agentDetails.subTabs.detailsTab', {
@@ -152,7 +156,18 @@ export const AgentDetailsPage: React.FunctionComponent = () => {
         isSelected: tabId === 'logs',
       },
     ];
-  }, [getHref, agentId, tabId]);
+    if (showRequestDiagnostics) {
+      tabs.push({
+        id: 'diagnostics',
+        name: i18n.translate('xpack.fleet.agentDetails.subTabs.diagnosticsTab', {
+          defaultMessage: 'Diagnostics',
+        }),
+        href: getHref('agent_details_diagnostics', { agentId, tabId: 'diagnostics' }),
+        isSelected: tabId === 'diagnostics',
+      });
+    }
+    return tabs;
+  }, [getHref, agentId, tabId, showRequestDiagnostics]);
 
   return (
     <AgentRefreshContext.Provider
@@ -222,6 +237,12 @@ const AgentDetailsPageContent: React.FunctionComponent<{
           return <AgentLogs agent={agent} agentPolicy={agentPolicy} />;
         }}
       />
+      <Route
+        path={FLEET_ROUTING_PATHS.agent_details_diagnostics}
+        render={() => {
+          return <AgentDiagnosticsTab agent={agent} />;
+        }}
+      />
       <Route
         path={FLEET_ROUTING_PATHS.agent_details}
         render={() => {
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/agent_activity_flyout.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/agent_activity_flyout.tsx
index d40948f2323c6..98d66d7c6dcd8 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/agent_activity_flyout.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/agent_activity_flyout.tsx
@@ -254,6 +254,11 @@ const actionNames: {
     cancelledText: 'update tags',
   },
   CANCEL: { inProgressText: 'Cancelling', completedText: 'cancelled', cancelledText: '' },
+  REQUEST_DIAGNOSTICS: {
+    inProgressText: 'Requesting diagnostics for',
+    completedText: 'requested diagnostics',
+    cancelledText: 'request diagnostics',
+  },
   SETTINGS: {
     inProgressText: 'Updating settings of',
     completedText: 'updated settings',
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/bulk_actions.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/bulk_actions.tsx
index 356753a0d0045..aa53c3d8f4040 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/bulk_actions.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/bulk_actions.tsx
@@ -25,9 +25,12 @@ import {
 } from '../../components';
 import { useLicense } from '../../../../hooks';
 import { LICENSE_FOR_SCHEDULE_UPGRADE } from '../../../../../../../common/constants';
+import { ExperimentalFeaturesService } from '../../../../services';
 
 import { getCommonTags } from '../utils';
 
+import { AgentRequestDiagnosticsModal } from '../../components/agent_request_diagnostics_modal';
+
 import type { SelectionMode } from './types';
 import { TagsAddRemove } from './tags_add_remove';
 
@@ -67,6 +70,8 @@ export const AgentBulkActions: React.FunctionComponent<Props> = ({
   const [isUnenrollModalOpen, setIsUnenrollModalOpen] = useState<boolean>(false);
   const [updateModalState, setUpgradeModalState] = useState({ isOpen: false, isScheduled: false });
   const [isTagAddVisible, setIsTagAddVisible] = useState<boolean>(false);
+  const [isRequestDiagnosticsModalOpen, setIsRequestDiagnosticsModalOpen] =
+    useState<boolean>(false);
 
   // Check if user is working with only inactive agents
   const atLeastOneActiveAgentSelected =
@@ -77,96 +82,120 @@ export const AgentBulkActions: React.FunctionComponent<Props> = ({
   const agentCount = selectionMode === 'manual' ? selectedAgents.length : totalActiveAgents;
   const agents = selectionMode === 'manual' ? selectedAgents : currentQuery;
   const [tagsPopoverButton, setTagsPopoverButton] = useState<HTMLElement>();
+  const { showRequestDiagnostics } = ExperimentalFeaturesService.get();
+
+  const menuItems = [
+    {
+      name: (
+        <FormattedMessage
+          id="xpack.fleet.agentBulkActions.addRemoveTags"
+          data-test-subj="agentBulkActionsAddRemoveTags"
+          defaultMessage="Add / remove tags"
+        />
+      ),
+      icon: <EuiIcon type="tag" size="m" />,
+      disabled: !atLeastOneActiveAgentSelected,
+      onClick: (event: any) => {
+        setTagsPopoverButton((event.target as Element).closest('button')!);
+        setIsTagAddVisible(!isTagAddVisible);
+      },
+    },
+    {
+      name: (
+        <FormattedMessage
+          id="xpack.fleet.agentBulkActions.reassignPolicy"
+          data-test-subj="agentBulkActionsReassign"
+          defaultMessage="Assign to new policy"
+        />
+      ),
+      icon: <EuiIcon type="pencil" size="m" />,
+      disabled: !atLeastOneActiveAgentSelected,
+      onClick: () => {
+        closeMenu();
+        setIsReassignFlyoutOpen(true);
+      },
+    },
+    {
+      name: (
+        <FormattedMessage
+          id="xpack.fleet.agentBulkActions.unenrollAgents"
+          data-test-subj="agentBulkActionsUnenroll"
+          defaultMessage="Unenroll {agentCount, plural, one {# agent} other {# agents}}"
+          values={{
+            agentCount,
+          }}
+        />
+      ),
+      icon: <EuiIcon type="trash" size="m" />,
+      disabled: !atLeastOneActiveAgentSelected,
+      onClick: () => {
+        closeMenu();
+        setIsUnenrollModalOpen(true);
+      },
+    },
+    {
+      name: (
+        <FormattedMessage
+          id="xpack.fleet.agentBulkActions.upgradeAgents"
+          data-test-subj="agentBulkActionsUpgrade"
+          defaultMessage="Upgrade {agentCount, plural, one {# agent} other {# agents}}"
+          values={{
+            agentCount,
+          }}
+        />
+      ),
+      icon: <EuiIcon type="refresh" size="m" />,
+      disabled: !atLeastOneActiveAgentSelected,
+      onClick: () => {
+        closeMenu();
+        setUpgradeModalState({ isOpen: true, isScheduled: false });
+      },
+    },
+    {
+      name: (
+        <FormattedMessage
+          id="xpack.fleet.agentBulkActions.scheduleUpgradeAgents"
+          data-test-subj="agentBulkActionsScheduleUpgrade"
+          defaultMessage="Schedule upgrade for {agentCount, plural, one {# agent} other {# agents}}"
+          values={{
+            agentCount,
+          }}
+        />
+      ),
+      icon: <EuiIcon type="timeRefresh" size="m" />,
+      disabled: !atLeastOneActiveAgentSelected || !isLicenceAllowingScheduleUpgrade,
+      onClick: () => {
+        closeMenu();
+        setUpgradeModalState({ isOpen: true, isScheduled: true });
+      },
+    },
+  ];
+
+  if (showRequestDiagnostics) {
+    menuItems.push({
+      name: (
+        <FormattedMessage
+          id="xpack.fleet.agentBulkActions.requestDiagnostics"
+          data-test-subj="agentBulkActionsRequestDiagnostics"
+          defaultMessage="Request diagnostics for {agentCount, plural, one {# agent} other {# agents}}"
+          values={{
+            agentCount,
+          }}
+        />
+      ),
+      icon: <EuiIcon type="trash" size="m" />,
+      disabled: !atLeastOneActiveAgentSelected,
+      onClick: () => {
+        closeMenu();
+        setIsRequestDiagnosticsModalOpen(true);
+      },
+    });
+  }
 
   const panels = [
     {
       id: 0,
-      items: [
-        {
-          name: (
-            <FormattedMessage
-              id="xpack.fleet.agentBulkActions.addRemoveTags"
-              data-test-subj="agentBulkActionsAddRemoveTags"
-              defaultMessage="Add / remove tags"
-            />
-          ),
-          icon: <EuiIcon type="tag" size="m" />,
-          disabled: !atLeastOneActiveAgentSelected,
-          onClick: (event: any) => {
-            setTagsPopoverButton((event.target as Element).closest('button')!);
-            setIsTagAddVisible(!isTagAddVisible);
-          },
-        },
-        {
-          name: (
-            <FormattedMessage
-              id="xpack.fleet.agentBulkActions.reassignPolicy"
-              data-test-subj="agentBulkActionsReassign"
-              defaultMessage="Assign to new policy"
-            />
-          ),
-          icon: <EuiIcon type="pencil" size="m" />,
-          disabled: !atLeastOneActiveAgentSelected,
-          onClick: () => {
-            closeMenu();
-            setIsReassignFlyoutOpen(true);
-          },
-        },
-        {
-          name: (
-            <FormattedMessage
-              id="xpack.fleet.agentBulkActions.unenrollAgents"
-              data-test-subj="agentBulkActionsUnenroll"
-              defaultMessage="Unenroll {agentCount, plural, one {# agent} other {# agents}}"
-              values={{
-                agentCount,
-              }}
-            />
-          ),
-          icon: <EuiIcon type="trash" size="m" />,
-          disabled: !atLeastOneActiveAgentSelected,
-          onClick: () => {
-            closeMenu();
-            setIsUnenrollModalOpen(true);
-          },
-        },
-        {
-          name: (
-            <FormattedMessage
-              id="xpack.fleet.agentBulkActions.upgradeAgents"
-              data-test-subj="agentBulkActionsUpgrade"
-              defaultMessage="Upgrade {agentCount, plural, one {# agent} other {# agents}}"
-              values={{
-                agentCount,
-              }}
-            />
-          ),
-          icon: <EuiIcon type="refresh" size="m" />,
-          disabled: !atLeastOneActiveAgentSelected,
-          onClick: () => {
-            closeMenu();
-            setUpgradeModalState({ isOpen: true, isScheduled: false });
-          },
-        },
-        {
-          name: (
-            <FormattedMessage
-              id="xpack.fleet.agentBulkActions.scheduleUpgradeAgents"
-              data-test-subj="agentBulkActionsScheduleUpgrade"
-              defaultMessage="Schedule upgrade for {agentCount, plural, one {# agent} other {# agents}}"
-              values={{
-                agentCount,
-              }}
-            />
-          ),
-          icon: <EuiIcon type="timeRefresh" size="m" />,
-          disabled: !atLeastOneActiveAgentSelected || !isLicenceAllowingScheduleUpgrade,
-          onClick: () => {
-            closeMenu();
-            setUpgradeModalState({ isOpen: true, isScheduled: true });
-          },
-        },
-      ],
+      items: menuItems,
     },
   ];
 
@@ -228,6 +257,17 @@ export const AgentBulkActions: React.FunctionComponent<Props> = ({
           }}
         />
       )}
+      {isRequestDiagnosticsModalOpen && (
+        <EuiPortal>
+          <AgentRequestDiagnosticsModal
+            agents={agents}
+            agentCount={agentCount}
+            onClose={() => {
+              setIsRequestDiagnosticsModalOpen(false);
+            }}
+          />
+        </EuiPortal>
+      )}
       <EuiFlexGroup gutterSize="m" alignItems="center">
         <EuiFlexItem grow={false}>
           <EuiPopover
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/search_and_filter_bar.test.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/search_and_filter_bar.test.tsx
index 33fd16419a1bd..f3de9cf503cf1 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/search_and_filter_bar.test.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/search_and_filter_bar.test.tsx
@@ -20,6 +20,8 @@ import { FleetStatusProvider, ConfigContext, KibanaVersionContext } from '../../
 
 import { getMockTheme } from '../../../../../../mocks';
 
+import { ExperimentalFeaturesService } from '../../../../services';
+
 import { SearchAndFilterBar } from './search_and_filter_bar';
 
 const mockTheme = getMockTheme({
@@ -49,6 +51,14 @@ const TestComponent = (props: any) => (
 );
 
 describe('SearchAndFilterBar', () => {
+  beforeAll(() => {
+    ExperimentalFeaturesService.init({
+      createPackagePolicyMultiPageLayout: true,
+      packageVerification: true,
+      showDevtoolsRequest: false,
+      showRequestDiagnostics: false,
+    });
+  });
   it('should show no Actions button when no agent is selected', async () => {
     const selectedAgents: Agent[] = [];
     const props: any = {
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/table_row_actions.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/table_row_actions.tsx
index 901d03ab7e371..ad9c9bdbf3f7b 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/table_row_actions.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/table_row_actions.tsx
@@ -13,6 +13,7 @@ import type { Agent, AgentPolicy } from '../../../../types';
 import { useAuthz, useLink, useKibanaVersion } from '../../../../hooks';
 import { ContextMenuActions } from '../../../../components';
 import { isAgentUpgradeable } from '../../../../services';
+import { ExperimentalFeaturesService } from '../../../../services';
 
 export const TableRowActions: React.FunctionComponent<{
   agent: Agent;
@@ -21,6 +22,7 @@ export const TableRowActions: React.FunctionComponent<{
   onUnenrollClick: () => void;
   onUpgradeClick: () => void;
   onAddRemoveTagsClick: (button: HTMLElement) => void;
+  onRequestDiagnosticsClick: () => void;
 }> = ({
   agent,
   agentPolicy,
@@ -28,6 +30,7 @@ export const TableRowActions: React.FunctionComponent<{
   onUnenrollClick,
   onUpgradeClick,
   onAddRemoveTagsClick,
+  onRequestDiagnosticsClick,
 }) => {
   const { getHref } = useLink();
   const hasFleetAllPrivileges = useAuthz().fleet.all;
@@ -35,6 +38,7 @@ export const TableRowActions: React.FunctionComponent<{
   const isUnenrolling = agent.status === 'unenrolling';
   const kibanaVersion = useKibanaVersion();
   const [isMenuOpen, setIsMenuOpen] = useState(false);
+  const { showRequestDiagnostics } = ExperimentalFeaturesService.get();
   const menuItems = [
     <EuiContextMenuItem
       icon="inspect"
@@ -105,6 +109,23 @@ export const TableRowActions: React.FunctionComponent<{
         />
       </EuiContextMenuItem>
     );
+
+    if (showRequestDiagnostics) {
+      menuItems.push(
+        <EuiContextMenuItem
+          icon="download"
+          disabled={!hasFleetAllPrivileges}
+          onClick={() => {
+            onRequestDiagnosticsClick();
+          }}
+        >
+          <FormattedMessage
+            id="xpack.fleet.agentList.diagnosticsOneButton"
+            defaultMessage="Request diagnostics .zip"
+          />
+        </EuiContextMenuItem>
+      );
+    }
   }
   return (
     <ContextMenuActions
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/index.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/index.tsx
index 4168dab8dceb1..452d7ec2ac0f6 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/index.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/index.tsx
@@ -51,6 +51,8 @@ import {
 } from '../components';
 import { useFleetServerUnhealthy } from '../hooks/use_fleet_server_unhealthy';
 
+import { AgentRequestDiagnosticsModal } from '../components/agent_request_diagnostics_modal';
+
 import { AgentTableHeader } from './components/table_header';
 import type { SelectionMode } from './components/types';
 import { SearchAndFilterBar } from './components/search_and_filter_bar';
@@ -146,6 +148,9 @@ export const AgentListPage: React.FunctionComponent<{}> = () => {
   const [agentToAddRemoveTags, setAgentToAddRemoveTags] = useState<Agent | undefined>(undefined);
   const [tagsPopoverButton, setTagsPopoverButton] = useState<HTMLElement>();
   const [showTagsAddRemove, setShowTagsAddRemove] = useState(false);
+  const [agentToRequestDiagnostics, setAgentToRequestDiagnostics] = useState<Agent | undefined>(
+    undefined
+  );
 
   // Kuery
   const kuery = useMemo(() => {
@@ -538,6 +543,7 @@ export const AgentListPage: React.FunctionComponent<{}> = () => {
                   setAgentToAddRemoveTags(agent);
                   setShowTagsAddRemove(!showTagsAddRemove);
                 }}
+                onRequestDiagnosticsClick={() => setAgentToRequestDiagnostics(agent)}
               />
             );
           },
@@ -612,6 +618,17 @@ export const AgentListPage: React.FunctionComponent<{}> = () => {
           />
         </EuiPortal>
       )}
+      {agentToRequestDiagnostics && (
+        <EuiPortal>
+          <AgentRequestDiagnosticsModal
+            agents={[agentToRequestDiagnostics]}
+            agentCount={1}
+            onClose={() => {
+              setAgentToRequestDiagnostics(undefined);
+            }}
+          />
+        </EuiPortal>
+      )}
       {showTagsAddRemove && (
         <TagsAddRemove
           agentId={agentToAddRemoveTags?.id!}
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/components/agent_request_diagnostics_modal/index.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/components/agent_request_diagnostics_modal/index.tsx
new file mode 100644
index 0000000000000..d5bb9adf040b2
--- /dev/null
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/components/agent_request_diagnostics_modal/index.tsx
@@ -0,0 +1,127 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import React, { useState } from 'react';
+import { useHistory } from 'react-router-dom';
+import { i18n } from '@kbn/i18n';
+import { EuiConfirmModal } from '@elastic/eui';
+import { FormattedMessage } from '@kbn/i18n-react';
+
+import type { Agent } from '../../../../types';
+import {
+  sendPostRequestDiagnostics,
+  sendPostBulkRequestDiagnostics,
+  useStartServices,
+  useLink,
+} from '../../../../hooks';
+
+interface Props {
+  onClose: () => void;
+  agents: Agent[] | string;
+  agentCount: number;
+}
+
+export const AgentRequestDiagnosticsModal: React.FunctionComponent<Props> = ({
+  onClose,
+  agents,
+  agentCount,
+}) => {
+  const { notifications } = useStartServices();
+  const [isSubmitting, setIsSubmitting] = useState(false);
+  const isSingleAgent = Array.isArray(agents) && agents.length === 1;
+  const { getPath } = useLink();
+  const history = useHistory();
+
+  async function onSubmit() {
+    try {
+      setIsSubmitting(true);
+
+      const { error } = isSingleAgent
+        ? await sendPostRequestDiagnostics((agents[0] as Agent).id)
+        : await sendPostBulkRequestDiagnostics({
+            agents: typeof agents === 'string' ? agents : agents.map((agent) => agent.id),
+          });
+      if (error) {
+        throw error;
+      }
+      setIsSubmitting(false);
+      const successMessage = i18n.translate(
+        'xpack.fleet.requestDiagnostics.successSingleNotificationTitle',
+        {
+          defaultMessage: 'Request diagnostics submitted',
+        }
+      );
+      notifications.toasts.addSuccess(successMessage);
+
+      if (isSingleAgent) {
+        const path = getPath('agent_details_diagnostics', { agentId: (agents[0] as Agent).id });
+        history.push(path);
+      }
+      onClose();
+    } catch (error) {
+      setIsSubmitting(false);
+      notifications.toasts.addError(error, {
+        title: i18n.translate('xpack.fleet.requestDiagnostics.fatalErrorNotificationTitle', {
+          defaultMessage:
+            'Error requesting diagnostics {count, plural, one {agent} other {agents}}',
+          values: { count: agentCount },
+        }),
+      });
+    }
+  }
+
+  return (
+    <EuiConfirmModal
+      data-test-subj="requestDiagnosticsModal"
+      title={
+        isSingleAgent ? (
+          <FormattedMessage
+            id="xpack.fleet.requestDiagnostics.singleTitle"
+            defaultMessage="Request diagnostics"
+          />
+        ) : (
+          <FormattedMessage
+            id="xpack.fleet.requestDiagnostics.multipleTitle"
+            defaultMessage="Request diagnostics for {count} agents"
+            values={{ count: agentCount }}
+          />
+        )
+      }
+      onCancel={onClose}
+      onConfirm={onSubmit}
+      cancelButtonText={
+        <FormattedMessage
+          id="xpack.fleet.requestDiagnostics.cancelButtonLabel"
+          defaultMessage="Cancel"
+        />
+      }
+      confirmButtonDisabled={isSubmitting}
+      confirmButtonText={
+        isSingleAgent ? (
+          <FormattedMessage
+            id="xpack.fleet.requestDiagnostics.confirmSingleButtonLabel"
+            defaultMessage="Request diagnostics"
+          />
+        ) : (
+          <FormattedMessage
+            id="xpack.fleet.requestDiagnostics.confirmMultipleButtonLabel"
+            defaultMessage="Request diagnostics for {count} agents"
+            values={{ count: agentCount }}
+          />
+        )
+      }
+      buttonColor="primary"
+    >
+      <p>
+        <FormattedMessage
+          id="xpack.fleet.requestDiagnostics.description"
+          defaultMessage="Diagnostics files are stored in Elasticsearch, and as such can incur storage costs. Fleet will automatically remove old diagnostics files after 30 days."
+        />
+      </p>
+    </EuiConfirmModal>
+  );
+};
diff --git a/x-pack/plugins/fleet/public/constants/page_paths.ts b/x-pack/plugins/fleet/public/constants/page_paths.ts
index d276d777661ed..4eba2304777da 100644
--- a/x-pack/plugins/fleet/public/constants/page_paths.ts
+++ b/x-pack/plugins/fleet/public/constants/page_paths.ts
@@ -41,6 +41,7 @@ export type DynamicPage =
   | 'agent_list'
   | 'agent_details'
   | 'agent_details_logs'
+  | 'agent_details_diagnostics'
   | 'settings_edit_outputs'
   | 'settings_edit_download_sources'
   | 'settings_edit_fleet_server_hosts';
@@ -61,6 +62,7 @@ export const FLEET_ROUTING_PATHS = {
   agents: '/agents',
   agent_details: '/agents/:agentId/:tabId?',
   agent_details_logs: '/agents/:agentId/logs',
+  agent_details_diagnostics: '/agents/:agentId/diagnostics',
   policies: '/policies',
   policies_list: '/policies',
   policy_details: '/policies/:policyId/:tabId?',
@@ -199,6 +201,7 @@ export const pagePathGetters: {
     `/agents/${agentId}${tabId ? `/${tabId}` : ''}${logQuery ? `?_q=${logQuery}` : ''}`,
   ],
   agent_details_logs: ({ agentId }) => [FLEET_BASE_PATH, `/agents/${agentId}/logs`],
+  agent_details_diagnostics: ({ agentId }) => [FLEET_BASE_PATH, `/agents/${agentId}/diagnostics`],
   enrollment_tokens: () => [FLEET_BASE_PATH, '/enrollment-tokens'],
   data_streams: () => [FLEET_BASE_PATH, '/data-streams'],
   settings: () => [FLEET_BASE_PATH, FLEET_ROUTING_PATHS.settings],
diff --git a/x-pack/plugins/fleet/public/hooks/use_request/agents.ts b/x-pack/plugins/fleet/public/hooks/use_request/agents.ts
index 13f687e321e54..0ebb99508bd84 100644
--- a/x-pack/plugins/fleet/public/hooks/use_request/agents.ts
+++ b/x-pack/plugins/fleet/public/hooks/use_request/agents.ts
@@ -8,7 +8,11 @@
 import type {
   GetActionStatusResponse,
   GetAgentTagsResponse,
+  GetAgentUploadsResponse,
+  PostBulkRequestDiagnosticsResponse,
   PostBulkUpdateAgentTagsRequest,
+  PostRequestBulkDiagnosticsRequest,
+  PostRequestDiagnosticsResponse,
   UpdateAgentRequest,
 } from '../../../common/types';
 
@@ -171,6 +175,42 @@ export function sendPostAgentUpgrade(
   });
 }
 
+export function sendPostRequestDiagnostics(agentId: string, options?: RequestOptions) {
+  return sendRequest<PostRequestDiagnosticsResponse>({
+    path: agentRouteService.getRequestDiagnosticsPath(agentId),
+    method: 'post',
+    ...options,
+  });
+}
+
+export function sendPostBulkRequestDiagnostics(
+  body: PostRequestBulkDiagnosticsRequest['body'],
+  options?: RequestOptions
+) {
+  return sendRequest<PostBulkRequestDiagnosticsResponse>({
+    path: agentRouteService.getBulkRequestDiagnosticsPath(),
+    method: 'post',
+    body,
+    ...options,
+  });
+}
+
+export function sendGetAgentUploads(agentId: string, options?: RequestOptions) {
+  return sendRequest<GetAgentUploadsResponse>({
+    path: agentRouteService.getListAgentUploads(agentId),
+    method: 'get',
+    ...options,
+  });
+}
+
+export const useGetAgentUploads = (agentId: string, options?: RequestOptions) => {
+  return useRequest<GetAgentUploadsResponse>({
+    path: agentRouteService.getListAgentUploads(agentId),
+    method: 'get',
+    ...options,
+  });
+};
+
 export function sendPostAgentAction(
   agentId: string,
   body: PostNewAgentActionRequest['body'],
diff --git a/x-pack/plugins/fleet/public/mock/create_test_renderer.tsx b/x-pack/plugins/fleet/public/mock/create_test_renderer.tsx
index 51ff2cb0f8245..f4cd7f9403280 100644
--- a/x-pack/plugins/fleet/public/mock/create_test_renderer.tsx
+++ b/x-pack/plugins/fleet/public/mock/create_test_renderer.tsx
@@ -68,6 +68,7 @@ export const createFleetTestRendererMock = (): TestRenderer => {
     createPackagePolicyMultiPageLayout: true,
     packageVerification: true,
     showDevtoolsRequest: false,
+    showRequestDiagnostics: false,
   });
 
   const HookWrapper = memo(({ children }) => {
diff --git a/x-pack/plugins/fleet/server/routes/agent/handlers.ts b/x-pack/plugins/fleet/server/routes/agent/handlers.ts
index 86f202381119f..85bcce7df69ba 100644
--- a/x-pack/plugins/fleet/server/routes/agent/handlers.ts
+++ b/x-pack/plugins/fleet/server/routes/agent/handlers.ts
@@ -28,6 +28,7 @@ import type {
   GetAgentTagsResponse,
   GetAvailableVersionsResponse,
   GetActionStatusResponse,
+  GetAgentUploadsResponse,
 } from '../../../common/types';
 import type {
   GetAgentsRequestSchema,
@@ -41,6 +42,7 @@ import type {
   PostBulkAgentReassignRequestSchema,
   PostBulkUpdateAgentTagsRequestSchema,
   GetActionStatusRequestSchema,
+  GetAgentUploadFileRequestSchema,
 } from '../../types';
 import { defaultFleetErrorHandler } from '../../errors';
 import * as AgentService from '../../services/agents';
@@ -362,3 +364,37 @@ export const getActionStatusHandler: RequestHandler<
     return defaultFleetErrorHandler({ error, response });
   }
 };
+
+export const getAgentUploadsHandler: RequestHandler<
+  TypeOf<typeof GetOneAgentRequestSchema.params>
+> = async (context, request, response) => {
+  const coreContext = await context.core;
+  const esClient = coreContext.elasticsearch.client.asInternalUser;
+  try {
+    const body: GetAgentUploadsResponse = {
+      items: await AgentService.getAgentUploads(esClient, request.params.agentId),
+    };
+
+    return response.ok({ body });
+  } catch (error) {
+    return defaultFleetErrorHandler({ error, response });
+  }
+};
+
+export const getAgentUploadFileHandler: RequestHandler<
+  TypeOf<typeof GetAgentUploadFileRequestSchema.params>
+> = async (context, request, response) => {
+  const coreContext = await context.core;
+  const esClient = coreContext.elasticsearch.client.asInternalUser;
+  try {
+    const resp = await AgentService.getAgentUploadFile(
+      esClient,
+      request.params.fileId,
+      request.params.fileName
+    );
+
+    return response.ok(resp);
+  } catch (error) {
+    return defaultFleetErrorHandler({ error, response });
+  }
+};
diff --git a/x-pack/plugins/fleet/server/routes/agent/index.ts b/x-pack/plugins/fleet/server/routes/agent/index.ts
index a6ee368a775ed..e8ac9a2de6749 100644
--- a/x-pack/plugins/fleet/server/routes/agent/index.ts
+++ b/x-pack/plugins/fleet/server/routes/agent/index.ts
@@ -23,6 +23,10 @@ import {
   PostBulkAgentUpgradeRequestSchema,
   PostCancelActionRequestSchema,
   GetActionStatusRequestSchema,
+  PostRequestDiagnosticsActionRequestSchema,
+  PostBulkRequestDiagnosticsActionRequestSchema,
+  ListAgentUploadsRequestSchema,
+  GetAgentUploadFileRequestSchema,
 } from '../../types';
 import * as AgentService from '../../services/agents';
 import type { FleetConfigType } from '../..';
@@ -43,6 +47,8 @@ import {
   bulkUpdateAgentTagsHandler,
   getAvailableVersionsHandler,
   getActionStatusHandler,
+  getAgentUploadsHandler,
+  getAgentUploadFileHandler,
 } from './handlers';
 import {
   postNewAgentActionHandlerBuilder,
@@ -54,6 +60,10 @@ import {
   postAgentUpgradeHandler,
   postBulkAgentsUpgradeHandler,
 } from './upgrade_handler';
+import {
+  bulkRequestDiagnosticsHandler,
+  requestDiagnosticsHandler,
+} from './request_diagnostics_handler';
 
 export const registerAPIRoutes = (router: FleetAuthzRouter, config: FleetConfigType) => {
   // Get one
@@ -178,6 +188,50 @@ export const registerAPIRoutes = (router: FleetAuthzRouter, config: FleetConfigT
     putAgentsReassignHandler
   );
 
+  router.post(
+    {
+      path: AGENT_API_ROUTES.REQUEST_DIAGNOSTICS_PATTERN,
+      validate: PostRequestDiagnosticsActionRequestSchema,
+      fleetAuthz: {
+        fleet: { all: true },
+      },
+    },
+    requestDiagnosticsHandler
+  );
+
+  router.post(
+    {
+      path: AGENT_API_ROUTES.BULK_REQUEST_DIAGNOSTICS_PATTERN,
+      validate: PostBulkRequestDiagnosticsActionRequestSchema,
+      fleetAuthz: {
+        fleet: { all: true },
+      },
+    },
+    bulkRequestDiagnosticsHandler
+  );
+
+  router.get(
+    {
+      path: AGENT_API_ROUTES.LIST_UPLOADS_PATTERN,
+      validate: ListAgentUploadsRequestSchema,
+      fleetAuthz: {
+        fleet: { all: true },
+      },
+    },
+    getAgentUploadsHandler
+  );
+
+  router.get(
+    {
+      path: AGENT_API_ROUTES.GET_UPLOAD_FILE_PATTERN,
+      validate: GetAgentUploadFileRequestSchema,
+      fleetAuthz: {
+        fleet: { all: true },
+      },
+    },
+    getAgentUploadFileHandler
+  );
+
   // Get agent status for policy
   router.get(
     {
diff --git a/x-pack/plugins/fleet/server/routes/agent/request_diagnostics_handler.ts b/x-pack/plugins/fleet/server/routes/agent/request_diagnostics_handler.ts
new file mode 100644
index 0000000000000..74452b0e055c7
--- /dev/null
+++ b/x-pack/plugins/fleet/server/routes/agent/request_diagnostics_handler.ts
@@ -0,0 +1,55 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import type { RequestHandler } from '@kbn/core/server';
+import type { TypeOf } from '@kbn/config-schema';
+
+import * as AgentService from '../../services/agents';
+import type {
+  PostBulkRequestDiagnosticsActionRequestSchema,
+  PostRequestDiagnosticsActionRequestSchema,
+} from '../../types';
+import { defaultFleetErrorHandler } from '../../errors';
+
+export const requestDiagnosticsHandler: RequestHandler<
+  TypeOf<typeof PostRequestDiagnosticsActionRequestSchema.params>,
+  undefined,
+  undefined
+> = async (context, request, response) => {
+  const coreContext = await context.core;
+  const esClient = coreContext.elasticsearch.client.asInternalUser;
+  try {
+    const result = await AgentService.requestDiagnostics(esClient, request.params.agentId);
+
+    return response.ok({ body: { actionId: result.actionId } });
+  } catch (error) {
+    return defaultFleetErrorHandler({ error, response });
+  }
+};
+
+export const bulkRequestDiagnosticsHandler: RequestHandler<
+  undefined,
+  undefined,
+  TypeOf<typeof PostBulkRequestDiagnosticsActionRequestSchema.body>
+> = async (context, request, response) => {
+  const coreContext = await context.core;
+  const esClient = coreContext.elasticsearch.client.asInternalUser;
+  const soClient = coreContext.savedObjects.client;
+  const agentOptions = Array.isArray(request.body.agents)
+    ? { agentIds: request.body.agents }
+    : { kuery: request.body.agents };
+  try {
+    const result = await AgentService.bulkRequestDiagnostics(esClient, soClient, {
+      ...agentOptions,
+      batchSize: request.body.batchSize,
+    });
+
+    return response.ok({ body: { actionId: result.actionId } });
+  } catch (error) {
+    return defaultFleetErrorHandler({ error, response });
+  }
+};
diff --git a/x-pack/plugins/fleet/server/services/agents/bulk_actions_resolver.ts b/x-pack/plugins/fleet/server/services/agents/bulk_actions_resolver.ts
index df776937e3719..b6ec1d082b39a 100644
--- a/x-pack/plugins/fleet/server/services/agents/bulk_actions_resolver.ts
+++ b/x-pack/plugins/fleet/server/services/agents/bulk_actions_resolver.ts
@@ -20,12 +20,14 @@ import { UpgradeActionRunner } from './upgrade_action_runner';
 import { UpdateAgentTagsActionRunner } from './update_agent_tags_action_runner';
 import { UnenrollActionRunner } from './unenroll_action_runner';
 import type { ActionParams, RetryParams } from './action_runner';
+import { RequestDiagnosticsActionRunner } from './request_diagnostics_action_runner';
 
 export enum BulkActionTaskType {
   REASSIGN_RETRY = 'fleet:reassign_action:retry',
   UNENROLL_RETRY = 'fleet:unenroll_action:retry',
   UPGRADE_RETRY = 'fleet:upgrade_action:retry',
   UPDATE_AGENT_TAGS_RETRY = 'fleet:update_agent_tags:retry',
+  REQUEST_DIAGNOSTICS_RETRY = 'fleet:request_diagnostics:retry',
 }
 
 /**
@@ -49,6 +51,7 @@ export class BulkActionsResolver {
         [BulkActionTaskType.REASSIGN_RETRY]: ReassignActionRunner,
         [BulkActionTaskType.UPDATE_AGENT_TAGS_RETRY]: UpdateAgentTagsActionRunner,
         [BulkActionTaskType.UPGRADE_RETRY]: UpgradeActionRunner,
+        [BulkActionTaskType.REQUEST_DIAGNOSTICS_RETRY]: RequestDiagnosticsActionRunner,
       };
 
       return createRetryTask(
diff --git a/x-pack/plugins/fleet/server/services/agents/index.ts b/x-pack/plugins/fleet/server/services/agents/index.ts
index 302790cf6ae6d..c5e1c199e6b82 100644
--- a/x-pack/plugins/fleet/server/services/agents/index.ts
+++ b/x-pack/plugins/fleet/server/services/agents/index.ts
@@ -15,6 +15,8 @@ export * from './reassign';
 export * from './setup';
 export * from './update_agent_tags';
 export * from './action_status';
+export * from './request_diagnostics';
+export { getAgentUploads, getAgentUploadFile } from './uploads';
 export { AgentServiceImpl } from './agent_service';
 export type { AgentClient, AgentService } from './agent_service';
 export { BulkActionsResolver } from './bulk_actions_resolver';
diff --git a/x-pack/plugins/fleet/server/services/agents/request_diagnostics.test.ts b/x-pack/plugins/fleet/server/services/agents/request_diagnostics.test.ts
new file mode 100644
index 0000000000000..05aa81be27612
--- /dev/null
+++ b/x-pack/plugins/fleet/server/services/agents/request_diagnostics.test.ts
@@ -0,0 +1,54 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { appContextService } from '../app_context';
+import { createAppContextStartContractMock } from '../../mocks';
+
+import { createClientMock } from './action.mock';
+import { bulkRequestDiagnostics, requestDiagnostics } from './request_diagnostics';
+
+describe('requestDiagnostics (singular)', () => {
+  it('can request diagnostics for single agent', async () => {
+    const { esClient, agentInRegularDoc } = createClientMock();
+    await requestDiagnostics(esClient, agentInRegularDoc._id);
+
+    expect(esClient.create).toHaveBeenCalledWith(
+      expect.objectContaining({
+        body: expect.objectContaining({
+          agents: ['agent-in-regular-policy'],
+          type: 'REQUEST_DIAGNOSTICS',
+        }),
+        index: '.fleet-actions',
+      })
+    );
+  });
+});
+
+describe('requestDiagnostics (plural)', () => {
+  beforeEach(async () => {
+    appContextService.start(createAppContextStartContractMock());
+  });
+
+  afterEach(() => {
+    appContextService.stop();
+  });
+  it('can request diagnostics for multiple agents', async () => {
+    const { soClient, esClient, agentInRegularDoc, agentInRegularDoc2 } = createClientMock();
+    const idsToUnenroll = [agentInRegularDoc._id, agentInRegularDoc2._id];
+    await bulkRequestDiagnostics(esClient, soClient, { agentIds: idsToUnenroll });
+
+    expect(esClient.create).toHaveBeenCalledWith(
+      expect.objectContaining({
+        body: expect.objectContaining({
+          agents: ['agent-in-regular-policy', 'agent-in-regular-policy2'],
+          type: 'REQUEST_DIAGNOSTICS',
+        }),
+        index: '.fleet-actions',
+      })
+    );
+  });
+});
diff --git a/x-pack/plugins/fleet/server/services/agents/request_diagnostics.ts b/x-pack/plugins/fleet/server/services/agents/request_diagnostics.ts
new file mode 100644
index 0000000000000..efb9812180580
--- /dev/null
+++ b/x-pack/plugins/fleet/server/services/agents/request_diagnostics.ts
@@ -0,0 +1,67 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import type { ElasticsearchClient, SavedObjectsClientContract } from '@kbn/core/server';
+
+import { SO_SEARCH_LIMIT } from '../../constants';
+
+import type { GetAgentsOptions } from '.';
+import { getAgents, getAgentsByKuery } from './crud';
+import { createAgentAction } from './actions';
+import { openPointInTime } from './crud';
+import {
+  RequestDiagnosticsActionRunner,
+  requestDiagnosticsBatch,
+} from './request_diagnostics_action_runner';
+
+export async function requestDiagnostics(
+  esClient: ElasticsearchClient,
+  agentId: string
+): Promise<{ actionId: string }> {
+  const response = await createAgentAction(esClient, {
+    agents: [agentId],
+    created_at: new Date().toISOString(),
+    type: 'REQUEST_DIAGNOSTICS',
+  });
+  return { actionId: response.id };
+}
+
+export async function bulkRequestDiagnostics(
+  esClient: ElasticsearchClient,
+  soClient: SavedObjectsClientContract,
+  options: GetAgentsOptions & {
+    batchSize?: number;
+  }
+): Promise<{ actionId: string }> {
+  if ('agentIds' in options) {
+    const givenAgents = await getAgents(esClient, options);
+    return await requestDiagnosticsBatch(esClient, givenAgents, {});
+  }
+
+  const batchSize = options.batchSize ?? SO_SEARCH_LIMIT;
+  const res = await getAgentsByKuery(esClient, {
+    kuery: options.kuery,
+    showInactive: false,
+    page: 1,
+    perPage: batchSize,
+  });
+  if (res.total <= batchSize) {
+    const givenAgents = await getAgents(esClient, options);
+    return await requestDiagnosticsBatch(esClient, givenAgents, {});
+  } else {
+    return await new RequestDiagnosticsActionRunner(
+      esClient,
+      soClient,
+      {
+        ...options,
+        batchSize,
+        total: res.total,
+      },
+      { pitId: await openPointInTime(esClient) }
+    ).runActionAsyncWithRetry();
+  }
+}
diff --git a/x-pack/plugins/fleet/server/services/agents/request_diagnostics_action_runner.ts b/x-pack/plugins/fleet/server/services/agents/request_diagnostics_action_runner.ts
new file mode 100644
index 0000000000000..4b3cca06d061c
--- /dev/null
+++ b/x-pack/plugins/fleet/server/services/agents/request_diagnostics_action_runner.ts
@@ -0,0 +1,57 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import uuid from 'uuid';
+import type { ElasticsearchClient } from '@kbn/core/server';
+
+import type { Agent } from '../../types';
+
+import { ActionRunner } from './action_runner';
+import { createAgentAction } from './actions';
+import { BulkActionTaskType } from './bulk_actions_resolver';
+
+export class RequestDiagnosticsActionRunner extends ActionRunner {
+  protected async processAgents(agents: Agent[]): Promise<{ actionId: string }> {
+    return await requestDiagnosticsBatch(this.esClient, agents, this.actionParams!);
+  }
+
+  protected getTaskType() {
+    return BulkActionTaskType.REQUEST_DIAGNOSTICS_RETRY;
+  }
+
+  protected getActionType() {
+    return 'REQUEST_DIAGNOSTICS';
+  }
+}
+
+export async function requestDiagnosticsBatch(
+  esClient: ElasticsearchClient,
+  givenAgents: Agent[],
+  options: {
+    actionId?: string;
+    total?: number;
+  }
+): Promise<{ actionId: string }> {
+  const now = new Date().toISOString();
+
+  const actionId = options.actionId ?? uuid();
+  const total = options.total ?? givenAgents.length;
+
+  const agentIds = givenAgents.map((agent) => agent.id);
+
+  await createAgentAction(esClient, {
+    id: actionId,
+    agents: agentIds,
+    created_at: now,
+    type: 'REQUEST_DIAGNOSTICS',
+    total,
+  });
+
+  return {
+    actionId,
+  };
+}
diff --git a/x-pack/plugins/fleet/server/services/agents/uploads.ts b/x-pack/plugins/fleet/server/services/agents/uploads.ts
new file mode 100644
index 0000000000000..2269a080e41b9
--- /dev/null
+++ b/x-pack/plugins/fleet/server/services/agents/uploads.ts
@@ -0,0 +1,181 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+import type { Readable } from 'stream';
+
+import moment from 'moment';
+import type { ElasticsearchClient } from '@kbn/core-elasticsearch-server';
+
+import { createEsFileClient } from '@kbn/files-plugin/server';
+
+import type { ResponseHeaders } from '@kbn/core-http-server';
+
+import type { AgentDiagnostics } from '../../../common/types/models';
+import { appContextService } from '../app_context';
+import {
+  AGENT_ACTIONS_INDEX,
+  agentRouteService,
+  AGENT_ACTIONS_RESULTS_INDEX,
+} from '../../../common';
+
+import { SO_SEARCH_LIMIT } from '../../constants';
+
+const FILE_STORAGE_METADATA_AGENT_INDEX = '.fleet-agent-files';
+const FILE_STORAGE_DATA_AGENT_INDEX = '.fleet-agent-file-data';
+
+export async function getAgentUploads(
+  esClient: ElasticsearchClient,
+  agentId: string
+): Promise<AgentDiagnostics[]> {
+  const getFile = async (fileId: string) => {
+    if (!fileId) return;
+    try {
+      const file = await esClient.get({
+        index: FILE_STORAGE_METADATA_AGENT_INDEX,
+        id: fileId,
+      });
+      return {
+        id: file._id,
+        ...(file._source as any)?.file,
+      };
+    } catch (err) {
+      if (err.statusCode === 404) {
+        appContextService.getLogger().debug(err);
+        return;
+      } else {
+        throw err;
+      }
+    }
+  };
+
+  const actions = await _getRequestDiagnosticsActions(esClient, agentId);
+
+  const results = [];
+  for (const action of actions) {
+    const file = await getFile(action.fileId);
+    const fileName = file?.name ?? `${moment(action.timestamp!).format('YYYY-MM-DD HH:mm:ss')}.zip`;
+    const filePath = file ? agentRouteService.getAgentFileDownloadLink(file.id, file.name) : '';
+    const result = {
+      actionId: action.actionId,
+      id: file?.id ?? action.actionId,
+      status: file?.Status ?? 'IN_PROGRESS',
+      name: fileName,
+      createTime: action.timestamp!,
+      filePath,
+    };
+    results.push(result);
+  }
+
+  return results;
+}
+
+async function _getRequestDiagnosticsActions(
+  esClient: ElasticsearchClient,
+  agentId: string
+): Promise<Array<{ actionId: string; timestamp?: string; fileId: string }>> {
+  const agentActionRes = await esClient.search<any>({
+    index: AGENT_ACTIONS_INDEX,
+    ignore_unavailable: true,
+    size: SO_SEARCH_LIMIT,
+    query: {
+      bool: {
+        must: [
+          {
+            term: {
+              type: 'REQUEST_DIAGNOSTICS',
+            },
+          },
+          {
+            term: {
+              agents: agentId,
+            },
+          },
+        ],
+      },
+    },
+  });
+
+  const agentActionIds = agentActionRes.hits.hits.map((hit) => hit._source?.action_id as string);
+
+  if (agentActionIds.length === 0) {
+    return [];
+  }
+
+  try {
+    const actionResults = await esClient.search<any>({
+      index: AGENT_ACTIONS_RESULTS_INDEX,
+      ignore_unavailable: true,
+      size: SO_SEARCH_LIMIT,
+      query: {
+        bool: {
+          must: [
+            {
+              terms: {
+                action_id: agentActionIds,
+              },
+            },
+            {
+              term: {
+                agent_id: agentId,
+              },
+            },
+          ],
+        },
+      },
+    });
+    return actionResults.hits.hits.map((hit) => ({
+      actionId: hit._source?.action_id as string,
+      timestamp: hit._source?.['@timestamp'],
+      fileId: hit._source?.data?.file_id as string,
+    }));
+  } catch (err) {
+    if (err.statusCode === 404) {
+      // .fleet-actions-results does not yet exist
+      appContextService.getLogger().debug(err);
+      return [];
+    } else {
+      throw err;
+    }
+  }
+}
+
+export async function getAgentUploadFile(
+  esClient: ElasticsearchClient,
+  id: string,
+  fileName: string
+): Promise<{ body: Readable; headers: ResponseHeaders }> {
+  try {
+    const fileClient = createEsFileClient({
+      blobStorageIndex: FILE_STORAGE_DATA_AGENT_INDEX,
+      metadataIndex: FILE_STORAGE_METADATA_AGENT_INDEX,
+      elasticsearchClient: esClient,
+      logger: appContextService.getLogger(),
+    });
+
+    const file = await fileClient.get({
+      id,
+    });
+
+    return {
+      body: await file.downloadContent(),
+      headers: getDownloadHeadersForFile(fileName),
+    };
+  } catch (error) {
+    appContextService.getLogger().error(error);
+    throw error;
+  }
+}
+
+export function getDownloadHeadersForFile(fileName: string): ResponseHeaders {
+  return {
+    'content-type': 'application/octet-stream',
+    // Note, this name can be overridden by the client if set via a "download" attribute on the HTML tag.
+    'content-disposition': `attachment; filename="${fileName}"`,
+    'cache-control': 'max-age=31536000, immutable',
+    // https://developer.mozilla.org/en-US/docs/Web/HTTP/Headers/X-Content-Type-Options
+    'x-content-type-options': 'nosniff',
+  };
+}
diff --git a/x-pack/plugins/fleet/server/types/rest_spec/agent.ts b/x-pack/plugins/fleet/server/types/rest_spec/agent.ts
index d87031cdad9d6..709e8e8d27159 100644
--- a/x-pack/plugins/fleet/server/types/rest_spec/agent.ts
+++ b/x-pack/plugins/fleet/server/types/rest_spec/agent.ts
@@ -113,6 +113,32 @@ export const PutAgentReassignRequestSchema = {
   }),
 };
 
+export const PostRequestDiagnosticsActionRequestSchema = {
+  params: schema.object({
+    agentId: schema.string(),
+  }),
+};
+
+export const PostBulkRequestDiagnosticsActionRequestSchema = {
+  body: schema.object({
+    agents: schema.oneOf([schema.arrayOf(schema.string()), schema.string()]),
+    batchSize: schema.maybe(schema.number()),
+  }),
+};
+
+export const ListAgentUploadsRequestSchema = {
+  params: schema.object({
+    agentId: schema.string(),
+  }),
+};
+
+export const GetAgentUploadFileRequestSchema = {
+  params: schema.object({
+    fileId: schema.string(),
+    fileName: schema.string(),
+  }),
+};
+
 export const PostBulkAgentReassignRequestSchema = {
   body: schema.object({
     policy_id: schema.string(),
diff --git a/x-pack/test/fleet_api_integration/apis/agents/index.js b/x-pack/test/fleet_api_integration/apis/agents/index.js
index 0ce4413f7c2cf..783775d53f265 100644
--- a/x-pack/test/fleet_api_integration/apis/agents/index.js
+++ b/x-pack/test/fleet_api_integration/apis/agents/index.js
@@ -18,5 +18,7 @@ export default function loadTests({ loadTestFile }) {
     loadTestFile(require.resolve('./update'));
     loadTestFile(require.resolve('./update_agent_tags'));
     loadTestFile(require.resolve('./available_versions'));
+    loadTestFile(require.resolve('./request_diagnostics'));
+    loadTestFile(require.resolve('./uploads'));
   });
 }
diff --git a/x-pack/test/fleet_api_integration/apis/agents/request_diagnostics.ts b/x-pack/test/fleet_api_integration/apis/agents/request_diagnostics.ts
new file mode 100644
index 0000000000000..7f5ad510723d3
--- /dev/null
+++ b/x-pack/test/fleet_api_integration/apis/agents/request_diagnostics.ts
@@ -0,0 +1,108 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import expect from '@kbn/expect';
+
+import { FtrProviderContext } from '../../../api_integration/ftr_provider_context';
+import { setupFleetAndAgents } from './services';
+import { skipIfNoDockerRegistry } from '../../helpers';
+
+export default function (providerContext: FtrProviderContext) {
+  const { getService } = providerContext;
+  const esArchiver = getService('esArchiver');
+  const supertest = getService('supertest');
+
+  describe('fleet_request_diagnostics', () => {
+    skipIfNoDockerRegistry(providerContext);
+    setupFleetAndAgents(providerContext);
+    beforeEach(async () => {
+      await esArchiver.unload('x-pack/test/functional/es_archives/fleet/empty_fleet_server');
+      await esArchiver.load('x-pack/test/functional/es_archives/fleet/agents');
+      await getService('supertest').post(`/api/fleet/setup`).set('kbn-xsrf', 'xxx').send();
+    });
+    afterEach(async () => {
+      await esArchiver.unload('x-pack/test/functional/es_archives/fleet/agents');
+      await esArchiver.load('x-pack/test/functional/es_archives/fleet/empty_fleet_server');
+    });
+
+    async function verifyActionResult(agentCount: number) {
+      const { body } = await supertest
+        .get(`/api/fleet/agents/action_status`)
+        .set('kbn-xsrf', 'xxx');
+      const actionStatus = body.items[0];
+
+      expect(actionStatus.nbAgentsActionCreated).to.eql(agentCount);
+    }
+
+    it('/agents/{agent_id}/request_diagnostics should work', async () => {
+      await supertest
+        .post(`/api/fleet/agents/agent1/request_diagnostics`)
+        .set('kbn-xsrf', 'xxx')
+        .expect(200);
+
+      verifyActionResult(1);
+    });
+
+    it('/agents/bulk_request_diagnostics should work for multiple agents by id', async () => {
+      await supertest
+        .post(`/api/fleet/agents/bulk_request_diagnostics`)
+        .set('kbn-xsrf', 'xxx')
+        .send({
+          agents: ['agent2', 'agent3'],
+        });
+
+      verifyActionResult(2);
+    });
+
+    it('/agents/bulk_request_diagnostics should work for multiple agents by kuery', async () => {
+      await supertest
+        .post(`/api/fleet/agents/bulk_request_diagnostics`)
+        .set('kbn-xsrf', 'xxx')
+        .send({
+          agents: '',
+        })
+        .expect(200);
+
+      verifyActionResult(4);
+    });
+
+    it('/agents/bulk_request_diagnostics should work for multiple agents by kuery in batches async', async () => {
+      const { body } = await supertest
+        .post(`/api/fleet/agents/bulk_request_diagnostics`)
+        .set('kbn-xsrf', 'xxx')
+        .send({
+          agents: '',
+          batchSize: 2,
+        })
+        .expect(200);
+
+      const actionId = body.actionId;
+
+      await new Promise((resolve, reject) => {
+        let attempts = 0;
+        const intervalId = setInterval(async () => {
+          if (attempts > 2) {
+            clearInterval(intervalId);
+            reject('action timed out');
+          }
+          ++attempts;
+          const {
+            body: { items: actionStatuses },
+          } = await supertest.get(`/api/fleet/agents/action_status`).set('kbn-xsrf', 'xxx');
+
+          const action = actionStatuses?.find((a: any) => a.actionId === actionId);
+          if (action && action.nbAgentsActioned === action.nbAgentsActionCreated) {
+            clearInterval(intervalId);
+            resolve({});
+          }
+        }, 1000);
+      }).catch((e) => {
+        throw e;
+      });
+    });
+  });
+}
diff --git a/x-pack/test/fleet_api_integration/apis/agents/uploads.ts b/x-pack/test/fleet_api_integration/apis/agents/uploads.ts
new file mode 100644
index 0000000000000..fc56b4fc46c18
--- /dev/null
+++ b/x-pack/test/fleet_api_integration/apis/agents/uploads.ts
@@ -0,0 +1,129 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import expect from '@kbn/expect';
+import { AGENT_ACTIONS_INDEX, AGENT_ACTIONS_RESULTS_INDEX } from '@kbn/fleet-plugin/common';
+import { FtrProviderContext } from '../../../api_integration/ftr_provider_context';
+import { setupFleetAndAgents } from './services';
+import { skipIfNoDockerRegistry } from '../../helpers';
+
+export default function (providerContext: FtrProviderContext) {
+  const { getService } = providerContext;
+  const esArchiver = getService('esArchiver');
+  const supertest = getService('supertest');
+  const esClient = getService('es');
+
+  const ES_INDEX_OPTIONS = { headers: { 'X-elastic-product-origin': 'fleet' } };
+
+  describe('fleet_uploads', () => {
+    skipIfNoDockerRegistry(providerContext);
+    setupFleetAndAgents(providerContext);
+
+    before(async () => {
+      await esArchiver.unload('x-pack/test/functional/es_archives/fleet/empty_fleet_server');
+      await getService('supertest').post(`/api/fleet/setup`).set('kbn-xsrf', 'xxx').send();
+
+      await esClient.create({
+        index: AGENT_ACTIONS_INDEX,
+        id: new Date().toISOString(),
+        refresh: true,
+        body: {
+          type: 'REQUEST_DIAGNOSTICS',
+          action_id: 'action1',
+          agents: ['agent1'],
+          '@timestamp': '2022-10-07T11:00:00.000Z',
+        },
+      });
+
+      await esClient.create(
+        {
+          index: AGENT_ACTIONS_RESULTS_INDEX,
+          id: new Date().toISOString(),
+          refresh: true,
+          body: {
+            action_id: 'action1',
+            agent_id: 'agent1',
+            '@timestamp': '2022-10-07T12:00:00.000Z',
+            data: {
+              file_id: 'file1',
+            },
+          },
+        },
+        ES_INDEX_OPTIONS
+      );
+
+      await esClient.update({
+        index: '.fleet-agent-files',
+        id: 'file1',
+        refresh: true,
+        body: {
+          doc_as_upsert: true,
+          doc: {
+            file: {
+              ChunkSize: 4194304,
+              extension: 'zip',
+              hash: {},
+              mime_type: 'application/zip',
+              mode: '0644',
+              name: 'elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip',
+              path: '/agent/elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip',
+              size: 24917,
+              Status: 'READY',
+              type: 'file',
+            },
+          },
+        },
+      });
+    });
+    after(async () => {
+      await esArchiver.load('x-pack/test/functional/es_archives/fleet/empty_fleet_server');
+    });
+
+    it('should get agent uploads', async () => {
+      const { body } = await supertest
+        .get(`/api/fleet/agents/agent1/uploads`)
+        .set('kbn-xsrf', 'xxx')
+        .expect(200);
+
+      expect(body.items[0]).to.eql({
+        actionId: 'action1',
+        createTime: '2022-10-07T12:00:00.000Z',
+        filePath:
+          '/api/fleet/agents/files/file1/elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip',
+        id: 'file1',
+        name: 'elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip',
+        status: 'READY',
+      });
+    });
+
+    it('should get agent uploaded file', async () => {
+      await esClient.update({
+        index: '.fleet-agent-file-data',
+        id: 'file1.0',
+        refresh: true,
+        body: {
+          doc_as_upsert: true,
+          doc: {
+            last: true,
+            bid: 'file1',
+            data: 'test',
+          },
+        },
+      });
+
+      const { header } = await supertest
+        .get(`/api/fleet/agents/files/file1/elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip`)
+        .set('kbn-xsrf', 'xxx')
+        .expect(200);
+
+      expect(header['content-type']).to.eql('application/octet-stream');
+      expect(header['content-disposition']).to.eql(
+        'attachment; filename="elastic-agent-diagnostics-2022-10-07T12-00-00Z-00.zip"'
+      );
+    });
+  });
+}
diff --git a/x-pack/test/plugin_api_integration/test_suites/task_manager/check_registered_task_types.ts b/x-pack/test/plugin_api_integration/test_suites/task_manager/check_registered_task_types.ts
index 518d36bbdc9a5..1bdfda2f63863 100644
--- a/x-pack/test/plugin_api_integration/test_suites/task_manager/check_registered_task_types.ts
+++ b/x-pack/test/plugin_api_integration/test_suites/task_manager/check_registered_task_types.ts
@@ -114,6 +114,7 @@ export default function ({ getService }: FtrProviderContext) {
         'endpoint:user-artifact-packager',
         'fleet:check-deleted-files-task',
         'fleet:reassign_action:retry',
+        'fleet:request_diagnostics:retry',
         'fleet:unenroll_action:retry',
         'fleet:update_agent_tags:retry',
         'fleet:upgrade_action:retry',