diff --git a/x-pack/plugins/osquery/cypress/integration/all/alerts.spec.ts b/x-pack/plugins/osquery/cypress/integration/all/alerts.spec.ts
index 21d3584b9fc46..4ef3e263df01c 100644
--- a/x-pack/plugins/osquery/cypress/integration/all/alerts.spec.ts
+++ b/x-pack/plugins/osquery/cypress/integration/all/alerts.spec.ts
@@ -34,10 +34,9 @@ describe('Alert Event Details', () => {
     runKbnArchiverScript(ArchiverMethod.UNLOAD, 'rule');
   });
 
-  it('should be able to run live query', () => {
+  it('should prepare packs and alert rules', () => {
     const PACK_NAME = 'testpack';
     const RULE_NAME = 'Test-rule';
-    const TIMELINE_NAME = 'Untitled timeline';
     navigateTo('/app/osquery/packs');
     preparePack(PACK_NAME);
     findAndClickButton('Edit');
@@ -57,8 +56,14 @@ describe('Alert Event Details', () => {
     cy.getBySel('ruleSwitch').should('have.attr', 'aria-checked', 'false');
     cy.getBySel('ruleSwitch').click();
     cy.getBySel('ruleSwitch').should('have.attr', 'aria-checked', 'true');
+  });
+
+  it('should be able to run live query and add to timeline (-depending on the previous test)', () => {
+    const TIMELINE_NAME = 'Untitled timeline';
     cy.visit('/app/security/alerts');
-    cy.wait(500);
+    cy.getBySel('header-page-title').contains('Alerts').should('exist');
+    cy.getBySel('timeline-context-menu-button').first().click({ force: true });
+    cy.getBySel('osquery-action-item').should('exist').contains('Run Osquery');
     cy.getBySel('expand-event').first().click();
     cy.getBySel('take-action-dropdown-btn').click();
     cy.getBySel('osquery-action-item').click();
diff --git a/x-pack/plugins/security_solution/common/ecs/agent/index.ts b/x-pack/plugins/security_solution/common/ecs/agent/index.ts
index 2332b60f1a3ca..7084214a9b876 100644
--- a/x-pack/plugins/security_solution/common/ecs/agent/index.ts
+++ b/x-pack/plugins/security_solution/common/ecs/agent/index.ts
@@ -7,4 +7,5 @@
 
 export interface AgentEcs {
   type?: string[];
+  id?: string[];
 }
diff --git a/x-pack/plugins/security_solution/public/detections/components/alerts_table/timeline_actions/alert_context_menu.tsx b/x-pack/plugins/security_solution/public/detections/components/alerts_table/timeline_actions/alert_context_menu.tsx
index 05a91f094ed38..efc4666b7bd61 100644
--- a/x-pack/plugins/security_solution/public/detections/components/alerts_table/timeline_actions/alert_context_menu.tsx
+++ b/x-pack/plugins/security_solution/public/detections/components/alerts_table/timeline_actions/alert_context_menu.tsx
@@ -13,6 +13,8 @@ import { connect, ConnectedProps } from 'react-redux';
 import { ExceptionListType } from '@kbn/securitysolution-io-ts-list-types';
 import { get } from 'lodash/fp';
 import { DEFAULT_ACTION_BUTTON_WIDTH } from '@kbn/timelines-plugin/public';
+import { useOsqueryContextActionItem } from '../../osquery/use_osquery_context_action_item';
+import { OsqueryFlyout } from '../../osquery/osquery_flyout';
 import { useRouteSpy } from '../../../../common/utils/route/use_route_spy';
 import { buildGetAlertByIdQuery } from '../../../../common/components/exceptions/helpers';
 import { useUserPrivileges } from '../../../../common/components/user_privileges';
@@ -63,6 +65,7 @@ const AlertContextMenuComponent: React.FC<AlertContextMenuProps & PropsFromRedux
   timelineQuery,
 }) => {
   const [isPopoverOpen, setPopover] = useState(false);
+  const [isOsqueryFlyoutOpen, setOsqueryFlyoutOpen] = useState(false);
   const [routeProps] = useRouteSpy();
 
   const onMenuItemClick = useCallback(() => {
@@ -186,18 +189,38 @@ const AlertContextMenuComponent: React.FC<AlertContextMenuProps & PropsFromRedux
       ? i18n.ACTION_ADD_EVENT_FILTER_DISABLED_TOOLTIP
       : undefined,
   });
+  const agentId = useMemo(() => get(0, ecsRowData?.agent?.id), [ecsRowData]);
+
+  const handleOnOsqueryClick = useCallback(() => {
+    setOsqueryFlyoutOpen((prevValue) => !prevValue);
+    setPopover(false);
+  }, []);
+
+  const { osqueryActionItems } = useOsqueryContextActionItem({ handleClick: handleOnOsqueryClick });
+
   const items: React.ReactElement[] = useMemo(
     () =>
       !isEvent && ruleId
-        ? [...addToCaseActionItems, ...statusActionItems, ...exceptionActionItems]
-        : [...addToCaseActionItems, ...eventFilterActionItems],
+        ? [
+            ...addToCaseActionItems,
+            ...statusActionItems,
+            ...exceptionActionItems,
+            ...(agentId ? osqueryActionItems : []),
+          ]
+        : [
+            ...addToCaseActionItems,
+            ...eventFilterActionItems,
+            ...(agentId ? osqueryActionItems : []),
+          ],
     [
-      statusActionItems,
-      addToCaseActionItems,
-      eventFilterActionItems,
-      exceptionActionItems,
       isEvent,
       ruleId,
+      addToCaseActionItems,
+      statusActionItems,
+      exceptionActionItems,
+      agentId,
+      osqueryActionItems,
+      eventFilterActionItems,
     ]
   );
 
@@ -239,6 +262,9 @@ const AlertContextMenuComponent: React.FC<AlertContextMenuProps & PropsFromRedux
       {isAddEventFilterModalOpen && ecsRowData != null && (
         <EventFiltersFlyout data={ecsRowData} onCancel={closeAddEventFilterModal} />
       )}
+      {isOsqueryFlyoutOpen && agentId && ecsRowData != null && (
+        <OsqueryFlyout agentId={agentId} onClose={handleOnOsqueryClick} />
+      )}
     </>
   );
 };
diff --git a/x-pack/plugins/security_solution/public/detections/components/osquery/osquery_action_item.tsx b/x-pack/plugins/security_solution/public/detections/components/osquery/osquery_action_item.tsx
index ca61e2f3ebf6d..e27a13ef217e3 100644
--- a/x-pack/plugins/security_solution/public/detections/components/osquery/osquery_action_item.tsx
+++ b/x-pack/plugins/security_solution/public/detections/components/osquery/osquery_action_item.tsx
@@ -13,14 +13,12 @@ interface IProps {
   handleClick: () => void;
 }
 
-export const OsqueryActionItem = ({ handleClick }: IProps) => {
-  return (
-    <EuiContextMenuItem
-      key="osquery-action-item"
-      data-test-subj="osquery-action-item"
-      onClick={handleClick}
-    >
-      {ACTION_OSQUERY}
-    </EuiContextMenuItem>
-  );
-};
+export const OsqueryActionItem = ({ handleClick }: IProps) => (
+  <EuiContextMenuItem
+    key="osquery-action-item"
+    data-test-subj="osquery-action-item"
+    onClick={handleClick}
+  >
+    {ACTION_OSQUERY}
+  </EuiContextMenuItem>
+);
diff --git a/x-pack/plugins/security_solution/public/detections/components/osquery/use_osquery_context_action_item.tsx b/x-pack/plugins/security_solution/public/detections/components/osquery/use_osquery_context_action_item.tsx
new file mode 100644
index 0000000000000..41a78eb32619f
--- /dev/null
+++ b/x-pack/plugins/security_solution/public/detections/components/osquery/use_osquery_context_action_item.tsx
@@ -0,0 +1,27 @@
+/*
+ * 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, { useMemo } from 'react';
+import { OsqueryActionItem } from './osquery_action_item';
+import { useKibana } from '../../../common/lib/kibana';
+
+interface IProps {
+  handleClick: () => void;
+}
+
+export const useOsqueryContextActionItem = ({ handleClick }: IProps) => {
+  const osqueryActionItem = useMemo(
+    () => <OsqueryActionItem handleClick={handleClick} />,
+    [handleClick]
+  );
+  const permissions = useKibana().services.application.capabilities.osquery;
+
+  return {
+    osqueryActionItems:
+      permissions?.writeLiveQueries || permissions?.runSavedQueries ? [osqueryActionItem] : [],
+  };
+};
diff --git a/x-pack/plugins/timelines/server/search_strategy/timeline/eql/helpers.test.ts b/x-pack/plugins/timelines/server/search_strategy/timeline/eql/helpers.test.ts
index 5c6a0ac0bd416..10a4fae0a036d 100644
--- a/x-pack/plugins/timelines/server/search_strategy/timeline/eql/helpers.test.ts
+++ b/x-pack/plugins/timelines/server/search_strategy/timeline/eql/helpers.test.ts
@@ -208,6 +208,9 @@ describe('Search Strategy EQL helper', () => {
                 "_id": "qhymg3cBX5UUcOOYP3Ec",
                 "_index": ".ds-logs-endpoint.events.security-default-2021.02.05-000005",
                 "agent": Object {
+                  "id": Array [
+                    "1d15cf9e-3dc7-5b97-f586-743f7c2518b2",
+                  ],
                   "type": Array [
                     "endpoint",
                   ],
@@ -335,6 +338,9 @@ describe('Search Strategy EQL helper', () => {
                 "_id": "qxymg3cBX5UUcOOYP3Ec",
                 "_index": ".ds-logs-endpoint.events.security-default-2021.02.05-000005",
                 "agent": Object {
+                  "id": Array [
+                    "1d15cf9e-3dc7-5b97-f586-743f7c2518b2",
+                  ],
                   "type": Array [
                     "endpoint",
                   ],
@@ -476,6 +482,9 @@ describe('Search Strategy EQL helper', () => {
                 "_id": "rBymg3cBX5UUcOOYP3Ec",
                 "_index": ".ds-logs-endpoint.events.security-default-2021.02.05-000005",
                 "agent": Object {
+                  "id": Array [
+                    "1d15cf9e-3dc7-5b97-f586-743f7c2518b2",
+                  ],
                   "type": Array [
                     "endpoint",
                   ],
@@ -592,6 +601,9 @@ describe('Search Strategy EQL helper', () => {
                 "_id": "pxymg3cBX5UUcOOYP3Ec",
                 "_index": ".ds-logs-endpoint.events.process-default-2021.02.02-000005",
                 "agent": Object {
+                  "id": Array [
+                    "1d15cf9e-3dc7-5b97-f586-743f7c2518b2",
+                  ],
                   "type": Array [
                     "endpoint",
                   ],
diff --git a/x-pack/plugins/timelines/server/search_strategy/timeline/factory/helpers/constants.ts b/x-pack/plugins/timelines/server/search_strategy/timeline/factory/helpers/constants.ts
index 211edec96b8ac..068b52b8cd821 100644
--- a/x-pack/plugins/timelines/server/search_strategy/timeline/factory/helpers/constants.ts
+++ b/x-pack/plugins/timelines/server/search_strategy/timeline/factory/helpers/constants.ts
@@ -94,6 +94,7 @@ export const TIMELINE_EVENTS_FIELDS = [
   'event.timezone',
   'event.type',
   'agent.type',
+  'agent.id',
   'auditd.result',
   'auditd.session',
   'auditd.data.acct',