diff --git a/api_docs/ml.json b/api_docs/ml.json
index 3a3463b7397e..efa66ac9c9e8 100644
--- a/api_docs/ml.json
+++ b/api_docs/ml.json
@@ -5498,17 +5498,11 @@
         "type": "Function",
         "children": [
           {
-            "type": "CompoundType",
+            "type": "Any",
             "label": "error",
-            "isRequired": false,
+            "isRequired": true,
             "signature": [
-              {
-                "pluginId": "ml",
-                "scope": "common",
-                "docId": "kibMlPluginApi",
-                "section": "def-common.ErrorType",
-                "text": "ErrorType"
-              }
+              "any"
             ],
             "description": [],
             "source": {
@@ -5518,9 +5512,7 @@
           }
         ],
         "signature": [
-          "(error: ",
-          "ErrorType",
-          ") => string"
+          "(error: any) => string"
         ],
         "description": [],
         "label": "extractErrorMessage",
diff --git a/api_docs/monitoring.json b/api_docs/monitoring.json
index 51f1231a42e2..b24cdd89e424 100644
--- a/api_docs/monitoring.json
+++ b/api_docs/monitoring.json
@@ -46,6 +46,34 @@
             "signature": [
               "() => void"
             ]
+          },
+          {
+            "tags": [],
+            "id": "def-server.IBulkUploader.start",
+            "type": "Function",
+            "label": "start",
+            "description": [],
+            "source": {
+              "path": "x-pack/plugins/monitoring/server/types.ts",
+              "lineNumber": 95
+            },
+            "signature": [
+              "() => void"
+            ]
+          },
+          {
+            "tags": [],
+            "id": "def-server.IBulkUploader.handleNotEnabled",
+            "type": "Function",
+            "label": "handleNotEnabled",
+            "description": [],
+            "source": {
+              "path": "x-pack/plugins/monitoring/server/types.ts",
+              "lineNumber": 96
+            },
+            "signature": [
+              "() => void"
+            ]
           }
         ],
         "source": {
@@ -106,7 +134,7 @@
           "description": [],
           "source": {
             "path": "x-pack/plugins/monitoring/server/types.ts",
-            "lineNumber": 98
+            "lineNumber": 100
           },
           "signature": [
             "() => any"
@@ -115,7 +143,7 @@
       ],
       "source": {
         "path": "x-pack/plugins/monitoring/server/types.ts",
-        "lineNumber": 97
+        "lineNumber": 99
       },
       "lifecycle": "setup",
       "initialIsOpen": true
diff --git a/x-pack/plugins/monitoring/server/cluster_alerts/alerts_cluster_search.js b/x-pack/plugins/monitoring/server/cluster_alerts/alerts_cluster_search.js
index 96c1edccd5ef..05f0524c1252 100644
--- a/x-pack/plugins/monitoring/server/cluster_alerts/alerts_cluster_search.js
+++ b/x-pack/plugins/monitoring/server/cluster_alerts/alerts_cluster_search.js
@@ -146,8 +146,8 @@ export function createFilterForTime(options) {
  * @param {Object} req Request object from the API route
  * @param {String} cluster The cluster being checked
  */
-export function alertsClusterSearch(req, alertsIndex, cluster, checkLicense, options = {}) {
-  const verification = verifyMonitoringLicense(req.server);
+export async function alertsClusterSearch(req, alertsIndex, cluster, checkLicense, options = {}) {
+  const verification = await verifyMonitoringLicense(req.server);
 
   if (!verification.enabled) {
     return Promise.resolve({ message: verification.message });
diff --git a/x-pack/plugins/monitoring/server/cluster_alerts/alerts_clusters_aggregation.js b/x-pack/plugins/monitoring/server/cluster_alerts/alerts_clusters_aggregation.js
index f6e7fb01b7c3..5c4194d06361 100644
--- a/x-pack/plugins/monitoring/server/cluster_alerts/alerts_clusters_aggregation.js
+++ b/x-pack/plugins/monitoring/server/cluster_alerts/alerts_clusters_aggregation.js
@@ -9,8 +9,8 @@ import { get, find } from 'lodash';
 import { verifyMonitoringLicense } from './verify_monitoring_license';
 import { i18n } from '@kbn/i18n';
 
-export function alertsClustersAggregation(req, alertsIndex, clusters, checkLicense) {
-  const verification = verifyMonitoringLicense(req.server);
+export async function alertsClustersAggregation(req, alertsIndex, clusters, checkLicense) {
+  const verification = await verifyMonitoringLicense(req.server);
 
   if (!verification.enabled) {
     // return metadata detailing that alerts is disabled because of the monitoring cluster license
diff --git a/x-pack/plugins/monitoring/server/cluster_alerts/verify_monitoring_license.js b/x-pack/plugins/monitoring/server/cluster_alerts/verify_monitoring_license.js
index 238e9daf4d84..e93db4ea9609 100644
--- a/x-pack/plugins/monitoring/server/cluster_alerts/verify_monitoring_license.js
+++ b/x-pack/plugins/monitoring/server/cluster_alerts/verify_monitoring_license.js
@@ -16,17 +16,18 @@ import { i18n } from '@kbn/i18n';
  * @param  {Object} server Server object containing config and plugins
  * @return {Boolean} {@code true} to indicate that cluster alerts can be used.
  */
-export function verifyMonitoringLicense(server) {
+export async function verifyMonitoringLicense(server) {
   const config = server.config();
 
   // if cluster alerts are enabled, then ensure that we can use it according to the license
   if (config.get('monitoring.cluster_alerts.enabled')) {
     const xpackInfo = get(server.plugins.monitoring, 'info');
     if (xpackInfo) {
-      const watcherFeature = xpackInfo.getWatcherFeature();
+      const licenseService = await xpackInfo.getLicenseService();
+      const watcherFeature = licenseService.getWatcherFeature();
       return {
         enabled: watcherFeature.isEnabled,
-        message: xpackInfo.getMessage(),
+        message: licenseService.getMessage(),
       };
     }
 
diff --git a/x-pack/plugins/monitoring/server/lib/cluster/get_clusters_from_request.js b/x-pack/plugins/monitoring/server/lib/cluster/get_clusters_from_request.js
index 990a4df85c5f..b282cf94ade2 100644
--- a/x-pack/plugins/monitoring/server/lib/cluster/get_clusters_from_request.js
+++ b/x-pack/plugins/monitoring/server/lib/cluster/get_clusters_from_request.js
@@ -127,8 +127,8 @@ export async function getClustersFromRequest(
         clusters.map((cluster) => cluster.cluster_uuid)
       );
 
+      const verification = await verifyMonitoringLicense(req.server);
       for (const cluster of clusters) {
-        const verification = verifyMonitoringLicense(req.server);
         if (!verification.enabled) {
           // return metadata detailing that alerts is disabled because of the monitoring cluster license
           cluster.alerts = {
diff --git a/x-pack/plugins/monitoring/server/lib/elasticsearch/verify_monitoring_auth.js b/x-pack/plugins/monitoring/server/lib/elasticsearch/verify_monitoring_auth.js
index 9d0de92bc1aa..1895c36699e5 100644
--- a/x-pack/plugins/monitoring/server/lib/elasticsearch/verify_monitoring_auth.js
+++ b/x-pack/plugins/monitoring/server/lib/elasticsearch/verify_monitoring_auth.js
@@ -20,7 +20,8 @@ export async function verifyMonitoringAuth(req) {
   const xpackInfo = get(req.server.plugins.monitoring, 'info');
 
   if (xpackInfo) {
-    const security = xpackInfo.getSecurityFeature();
+    const licenseService = await xpackInfo.getLicenseService();
+    const security = licenseService.getSecurityFeature();
 
     // we only need to verify permissions if we're using X-Pack Security
     if (security.isAvailable && security.isEnabled) {
diff --git a/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.js b/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.js
index e0b8d2c0d098..000c26bff48a 100644
--- a/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.js
+++ b/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.js
@@ -234,7 +234,8 @@ function isBeatFromAPM(bucket) {
 }
 
 async function hasNecessaryPermissions(req) {
-  const securityFeature = req.server.plugins.monitoring.info.getSecurityFeature();
+  const licenseService = await req.server.plugins.monitoring.info.getLicenseService();
+  const securityFeature = licenseService.getSecurityFeature();
   if (!securityFeature.isAvailable || !securityFeature.isEnabled) {
     return true;
   }
diff --git a/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.test.js b/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.test.js
index 2d99443dac3d..437e07512d46 100644
--- a/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.test.js
+++ b/x-pack/plugins/monitoring/server/lib/setup/collection/get_collection_status.test.js
@@ -47,12 +47,14 @@ const mockReq = (
       plugins: {
         monitoring: {
           info: {
-            getSecurityFeature: () => {
-              return {
-                isAvailable: securityEnabled,
-                isEnabled: securityEnabled,
-              };
-            },
+            getLicenseService: () => ({
+              getSecurityFeature: () => {
+                return {
+                  isAvailable: securityEnabled,
+                  isEnabled: securityEnabled,
+                };
+              },
+            }),
           },
         },
         elasticsearch: {
diff --git a/x-pack/plugins/monitoring/server/license_service.ts b/x-pack/plugins/monitoring/server/license_service.ts
index efd1991688ee..fde22aaefa5d 100644
--- a/x-pack/plugins/monitoring/server/license_service.ts
+++ b/x-pack/plugins/monitoring/server/license_service.ts
@@ -8,13 +8,13 @@
 import { Subscription } from 'rxjs';
 import { ILegacyCustomClusterClient } from 'kibana/server';
 import { ILicense, LicenseFeature } from '../../licensing/common/types';
-import { LicensingPluginSetup } from '../../licensing/server';
+import { LicensingPluginStart } from '../../licensing/server';
 import { MonitoringConfig } from './config';
 import { Logger } from '../../../../src/core/server';
 import { MonitoringLicenseService } from './types';
 
 interface SetupDeps {
-  licensing: LicensingPluginSetup;
+  licensing: LicensingPluginStart;
   monitoringClient: ILegacyCustomClusterClient;
   config: MonitoringConfig;
   log: Logger;
diff --git a/x-pack/plugins/monitoring/server/plugin.ts b/x-pack/plugins/monitoring/server/plugin.ts
index a3fc82109849..e7606ece4457 100644
--- a/x-pack/plugins/monitoring/server/plugin.ts
+++ b/x-pack/plugins/monitoring/server/plugin.ts
@@ -105,15 +105,6 @@ export class MonitoringPlugin
       core.elasticsearch.legacy.createClient
     ));
 
-    // Start our license service which will ensure
-    // the appropriate licenses are present
-    this.licenseService = new LicenseService().setup({
-      licensing: plugins.licensing,
-      monitoringClient: cluster,
-      config,
-      log: this.log,
-    });
-
     Globals.init(core, plugins.cloud, cluster, config, this.getLogger);
     const serverInfo = core.http.getServerInfo();
     const alerts = AlertsFactory.getAll();
@@ -165,34 +156,6 @@ export class MonitoringPlugin
       },
     }));
 
-    // If collection is enabled, start it
-    const kibanaCollectionEnabled = config.kibana.collection.enabled;
-    if (kibanaCollectionEnabled) {
-      // Do not use `this.licenseService` as that looks at the monitoring cluster
-      // whereas we want to check the production cluster here
-      if (plugins.licensing) {
-        plugins.licensing.license$.subscribe((license: any) => {
-          // use updated xpack license info to start/stop bulk upload
-          const mainMonitoring = license.getFeature('monitoring');
-          const monitoringBulkEnabled =
-            mainMonitoring && mainMonitoring.isAvailable && mainMonitoring.isEnabled;
-          if (monitoringBulkEnabled) {
-            bulkUploader.start();
-          } else {
-            bulkUploader.handleNotEnabled();
-          }
-        });
-      } else {
-        kibanaMonitoringLog.warn(
-          'Internal collection for Kibana monitoring is disabled due to missing license information.'
-        );
-      }
-    } else {
-      kibanaMonitoringLog.info(
-        'Internal collection for Kibana monitoring is disabled per configuration.'
-      );
-    }
-
     // If the UI is enabled, then we want to register it so it shows up
     // and start any other UI-related setup tasks
     if (config.ui.enabled) {
@@ -201,7 +164,6 @@ export class MonitoringPlugin
         config,
         legacyConfig,
         core.getStartServices as () => Promise<[CoreStart, PluginsStart, {}]>,
-        this.licenseService,
         this.cluster,
         plugins
       );
@@ -224,7 +186,46 @@ export class MonitoringPlugin
     };
   }
 
-  start() {}
+  async start(core: CoreStart, { licensing }: PluginsStart) {
+    const config = createConfig(this.initializerContext.config.get<TypeOf<typeof configSchema>>());
+    // Start our license service which will ensure
+    // the appropriate licenses are present
+    this.licenseService = new LicenseService().setup({
+      licensing,
+      monitoringClient: this.cluster,
+      config,
+      log: this.log,
+    });
+
+    // If collection is enabled, start it
+    const kibanaMonitoringLog = this.getLogger(KIBANA_MONITORING_LOGGING_TAG);
+    const kibanaCollectionEnabled = config.kibana.collection.enabled;
+    if (kibanaCollectionEnabled) {
+      // Do not use `this.licenseService` as that looks at the monitoring cluster
+      // whereas we want to check the production cluster here
+      if (this.bulkUploader && licensing) {
+        licensing.license$.subscribe((license: any) => {
+          // use updated xpack license info to start/stop bulk upload
+          const mainMonitoring = license.getFeature('monitoring');
+          const monitoringBulkEnabled =
+            mainMonitoring && mainMonitoring.isAvailable && mainMonitoring.isEnabled;
+          if (monitoringBulkEnabled) {
+            this.bulkUploader?.start();
+          } else {
+            this.bulkUploader?.handleNotEnabled();
+          }
+        });
+      } else {
+        kibanaMonitoringLog.warn(
+          'Internal collection for Kibana monitoring is disabled due to missing license information.'
+        );
+      }
+    } else {
+      kibanaMonitoringLog.info(
+        'Internal collection for Kibana monitoring is disabled per configuration.'
+      );
+    }
+  }
 
   stop() {
     if (this.cluster) {
@@ -276,7 +277,6 @@ export class MonitoringPlugin
     config: MonitoringConfig,
     legacyConfig: any,
     getCoreServices: () => Promise<[CoreStart, PluginsStart, {}]>,
-    licenseService: MonitoringLicenseService,
     cluster: ILegacyCustomClusterClient,
     setupPlugins: PluginsSetup
   ): MonitoringCore {
@@ -343,7 +343,9 @@ export class MonitoringPlugin
               },
               plugins: {
                 monitoring: {
-                  info: licenseService,
+                  info: {
+                    getLicenseService: () => this.licenseService,
+                  },
                 },
                 elasticsearch: {
                   getCluster: (name: string) => ({
diff --git a/x-pack/plugins/monitoring/server/types.ts b/x-pack/plugins/monitoring/server/types.ts
index 4a8aba0de6bb..c0bfe32079cd 100644
--- a/x-pack/plugins/monitoring/server/types.ts
+++ b/x-pack/plugins/monitoring/server/types.ts
@@ -25,7 +25,7 @@ import {
   PluginSetupContract as AlertingPluginSetupContract,
 } from '../../alerting/server';
 import { InfraPluginSetup } from '../../infra/server';
-import { LicensingPluginSetup } from '../../licensing/server';
+import { LicensingPluginStart } from '../../licensing/server';
 import { PluginSetupContract as FeaturesPluginSetupContract } from '../../features/server';
 import { EncryptedSavedObjectsPluginSetup } from '../../encrypted_saved_objects/server';
 import { CloudSetup } from '../../cloud/server';
@@ -47,7 +47,6 @@ export interface MonitoringElasticsearchConfig {
 export interface PluginsSetup {
   encryptedSavedObjects?: EncryptedSavedObjectsPluginSetup;
   usageCollection?: UsageCollectionSetup;
-  licensing: LicensingPluginSetup;
   features: FeaturesPluginSetupContract;
   alerting?: AlertingPluginSetupContract;
   infra: InfraPluginSetup;
@@ -62,6 +61,7 @@ export interface RequestHandlerContextMonitoringPlugin extends RequestHandlerCon
 export interface PluginsStart {
   alerting: AlertingPluginStartContract;
   actions: ActionsPluginsStartContact;
+  licensing: LicensingPluginStart;
 }
 
 export interface MonitoringCoreConfig {
@@ -92,6 +92,8 @@ export interface LegacyShimDependencies {
 export interface IBulkUploader {
   getKibanaStats: () => any;
   stop: () => void;
+  start: () => void;
+  handleNotEnabled: () => void;
 }
 
 export interface MonitoringPluginSetup {
@@ -127,7 +129,9 @@ export interface LegacyServer {
   };
   plugins: {
     monitoring: {
-      info: MonitoringLicenseService;
+      info: {
+        getLicenseService: () => MonitoringLicenseService;
+      };
     };
     elasticsearch: {
       getCluster: (