diff --git a/src/notebooks/controllers/notebookControllerManager.node.ts b/src/notebooks/controllers/notebookControllerManager.node.ts
index 3452debe64b..1d8fcc407df 100644
--- a/src/notebooks/controllers/notebookControllerManager.node.ts
+++ b/src/notebooks/controllers/notebookControllerManager.node.ts
@@ -112,6 +112,12 @@ export class NotebookControllerManager implements INotebookControllerManager, IE
     private get isLocalLaunch(): boolean {
         return isLocalLaunch(this.configuration);
     }
+    private startTimeForFetchingControllers?: StopWatch;
+    private readonly controllerLoadingTelemetry = {
+        loadWithoutCacheSent: false,
+        loadWithCacheSent: false,
+        loadRemoteSent: false
+    };
     private wasPythonInstalledWhenFetchingControllers?: boolean;
     private interactiveNoPythonController?: NoPythonKernelsNotebookController;
     private notebookNoPythonController?: NoPythonKernelsNotebookController;
@@ -204,10 +210,24 @@ export class NotebookControllerManager implements INotebookControllerManager, IE
     // Find all the notebook controllers that we have registered
     public async loadNotebookControllers(refresh?: boolean): Promise<void> {
         if (!this.controllersPromise || refresh) {
+            this.startTimeForFetchingControllers = this.startTimeForFetchingControllers || new StopWatch();
             const stopWatch = new StopWatch();
 
             // Fetch the list of kernels ignoring the cache.
             this.loadLocalNotebookControllersImpl('ignoreCache')
+                .then(() => {
+                    if (!this.controllerLoadingTelemetry.loadWithoutCacheSent && this.startTimeForFetchingControllers) {
+                        this.controllerLoadingTelemetry.loadWithoutCacheSent = true;
+                        sendTelemetryEvent(
+                            Telemetry.FetchControllers,
+                            this.startTimeForFetchingControllers.elapsedTime,
+                            {
+                                firstTime: true,
+                                kind: 'local'
+                            }
+                        );
+                    }
+                })
                 .catch((ex) => traceError('Failed to fetch controllers without cache', ex))
                 .finally(() => {
                     this._controllersLoaded = true;
@@ -239,9 +259,37 @@ export class NotebookControllerManager implements INotebookControllerManager, IE
             // Fetch kernel the fastest possible way (local kernels from cache but remote fetch latest).
             // Fetch the list of kernels from the cache (note: if there's nothing in the case, it will fallback to searching).
             // Fetching remote kernels cannot be done from cache.
-            const promises = [this.loadLocalNotebookControllersImpl('useCache')];
+            const promises = [
+                this.loadLocalNotebookControllersImpl('useCache').then(() => {
+                    if (!this.controllerLoadingTelemetry.loadWithCacheSent && this.startTimeForFetchingControllers) {
+                        this.controllerLoadingTelemetry.loadWithCacheSent = true;
+                        sendTelemetryEvent(
+                            Telemetry.FetchControllers,
+                            this.startTimeForFetchingControllers.elapsedTime,
+                            {
+                                firstTime: false,
+                                kind: 'local'
+                            }
+                        );
+                    }
+                })
+            ];
             if (!this.isLocalLaunch) {
-                promises.push(this.loadRemoteNotebookControllersImpl());
+                promises.push(
+                    this.loadRemoteNotebookControllersImpl().then(() => {
+                        if (!this.controllerLoadingTelemetry.loadRemoteSent && this.startTimeForFetchingControllers) {
+                            this.controllerLoadingTelemetry.loadRemoteSent = true;
+                            sendTelemetryEvent(
+                                Telemetry.FetchControllers,
+                                this.startTimeForFetchingControllers.elapsedTime,
+                                {
+                                    firstTime: true,
+                                    kind: 'remote'
+                                }
+                            );
+                        }
+                    })
+                );
             }
             this.controllersPromise = Promise.all(promises)
                 .then(() => noop())
diff --git a/src/telemetry/index.ts b/src/telemetry/index.ts
index b9618d7b177..78811f43251 100644
--- a/src/telemetry/index.ts
+++ b/src/telemetry/index.ts
@@ -1533,4 +1533,18 @@ export interface IEventNamePropertyMapping {
     [Telemetry.KernelCrash]: never | undefined;
     [Telemetry.JupyterKernelHiddenViaFilter]: never | undefined;
     [Telemetry.JupyterKernelFilterUsed]: never | undefined;
+    /**
+     * Telemetry sent when we have loaded some controllers.
+     */
+    [Telemetry.FetchControllers]: {
+        /**
+         * Whether this is the first time we're loading this (same as not using caches).
+         * In the case of remotes, this is always `true` (as we don't cache anything for remote kernels).
+         */
+        firstTime: boolean;
+        /**
+         * Whether we've loaded local or remote controllers.
+         */
+        kind: 'local' | 'remote';
+    };
 }
diff --git a/src/webviews/webview-side/common/constants.ts b/src/webviews/webview-side/common/constants.ts
index 347e159dc94..843935a7fb3 100644
--- a/src/webviews/webview-side/common/constants.ts
+++ b/src/webviews/webview-side/common/constants.ts
@@ -299,6 +299,7 @@ export enum Telemetry {
      */
     ExportNotebookAsFailed = 'DATASCIENCE.EXPORT_NOTEBOOK_AS_FAILED',
     FailedToCreateNotebookController = 'DATASCIENCE.FAILED_TO_CREATE_CONTROLLER',
+    FetchControllers = 'DATASCIENCE.FETCH_CONTROLLERS',
     FailedToFindKernelSpecInterpreterForInteractive = 'DATASCIENCE.FAILED_TO_FIND_INTERPRETER_KERNEL_CONNECTION_FOR_INTERACTIVE',
 
     StartJupyter = 'DS_INTERNAL.JUPYTERSTARTUPCOST',