diff --git a/CHANGELOG.md b/CHANGELOG.md
index e28e586470ee..e231721de64e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -29,6 +29,10 @@
    ([#10049](https://github.com/Microsoft/vscode-python/issues/10049))
 1. Track cold/warm times to execute notebook cells.
    ([#10176](https://github.com/Microsoft/vscode-python/issues/10176))
+1. Telemetry to capture connections to `localhost` using the connect to remote Jupyter server feature.
+   ([#10098](https://github.com/Microsoft/vscode-python/issues/10098))
+1. Telemetry to capture perceived startup times of Jupyter and time to execute a cell.
+   ([#10212](https://github.com/Microsoft/vscode-python/issues/10212))
 
 ### Thanks
 
diff --git a/src/client/datascience/constants.ts b/src/client/datascience/constants.ts
index 07f4e8959013..6bd07eeed2c5 100644
--- a/src/client/datascience/constants.ts
+++ b/src/client/datascience/constants.ts
@@ -160,6 +160,7 @@ export enum Telemetry {
     SubmitCellThroughInput = 'DATASCIENCE.SUBMITCELLFROMREPL',
     ConnectLocalJupyter = 'DS_INTERNAL.CONNECTLOCALJUPYTER',
     ConnectRemoteJupyter = 'DS_INTERNAL.CONNECTREMOTEJUPYTER',
+    ConnectRemoteJupyterViaLocalHost = 'DS_INTERNAL.CONNECTREMOTEJUPYTER_VIA_LOCALHOST',
     ConnectFailedJupyter = 'DS_INTERNAL.CONNECTFAILEDJUPYTER',
     ConnectRemoteFailedJupyter = 'DS_INTERNAL.CONNECTREMOTEFAILEDJUPYTER',
     StartSessionFailedJupyter = 'DS_INTERNAL.START_SESSION_FAILED_JUPYTER',
@@ -209,6 +210,8 @@ export enum Telemetry {
     ExecuteCell = 'DATASCIENCE.EXECUTE_CELL_TIME',
     ExecuteCellPerceivedCold = 'DS_INTERNAL.EXECUTE_CELL_PERCEIVED_COLD',
     ExecuteCellPerceivedWarm = 'DS_INTERNAL.EXECUTE_CELL_PERCEIVED_WARM',
+    PerceivedJupyterStartupNotebook = 'DS_INTERNAL.PERCEIVED_JUPYTER_STARTUP_NOTEBOOK',
+    StartExecuteNotebookCellPerceivedCold = 'DS_INTERNAL.START_EXECUTE_NOTEBOOK_CELL_PERCEIVED_COLD',
     WebviewStartup = 'DS_INTERNAL.WEBVIEW_STARTUP',
     VariableExplorerFetchTime = 'DS_INTERNAL.VARIABLE_EXPLORER_FETCH_TIME',
     WebviewStyleUpdate = 'DS_INTERNAL.WEBVIEW_STYLE_UPDATE',
diff --git a/src/client/datascience/interactive-common/interactiveBase.ts b/src/client/datascience/interactive-common/interactiveBase.ts
index 7c89937cefb9..a678ac389400 100644
--- a/src/client/datascience/interactive-common/interactiveBase.ts
+++ b/src/client/datascience/interactive-common/interactiveBase.ts
@@ -20,6 +20,7 @@ import { IFileSystem } from '../../common/platform/types';
 import { IConfigurationService, IDisposableRegistry, IExperimentsManager } from '../../common/types';
 import { createDeferred, Deferred } from '../../common/utils/async';
 import * as localize from '../../common/utils/localize';
+import { StopWatch } from '../../common/utils/stopWatch';
 import { IInterpreterService, PythonInterpreter } from '../../interpreter/contracts';
 import { captureTelemetry, sendTelemetryEvent } from '../../telemetry';
 import { generateCellRangesFromDocument } from '../cellFactory';
@@ -78,6 +79,7 @@ import { InteractiveWindowMessageListener } from './interactiveWindowMessageList
 export abstract class InteractiveBase extends WebViewHost<IInteractiveWindowMapping> implements IInteractiveBase {
     private unfinishedCells: ICell[] = [];
     private restartingKernel: boolean = false;
+    private perceivedJupyterStartupTelemetryCaptured: boolean = false;
     private potentiallyUnfinishedStatus: Disposable[] = [];
     private addSysInfoPromise: Deferred<boolean> | undefined;
     private _notebook: INotebook | undefined;
@@ -457,8 +459,8 @@ export abstract class InteractiveBase extends WebViewHost<IInteractiveWindowMapp
     // tslint:disable-next-line: max-func-body-length
     protected async submitCode(code: string, file: string, line: number, id?: string, _editor?: TextEditor, debug?: boolean): Promise<boolean> {
         traceInfo(`Submitting code for ${this.id}`);
+        const stopWatch = this._notebook && !this.perceivedJupyterStartupTelemetryCaptured ? new StopWatch() : undefined;
         let result = true;
-
         // Do not execute or render empty code cells
         const cellMatcher = new CellMatcher(this.configService.getSettings().datascience);
         if (cellMatcher.stripFirstMarker(code).length === 0) {
@@ -511,7 +513,16 @@ export abstract class InteractiveBase extends WebViewHost<IInteractiveWindowMapp
                 if (file !== Identifiers.EmptyFileName) {
                     await this._notebook.execute(`__file__ = '${file.replace(/\\/g, '\\\\')}'`, file, line, uuid(), undefined, true);
                 }
-
+                if (stopWatch && !this.perceivedJupyterStartupTelemetryCaptured) {
+                    this.perceivedJupyterStartupTelemetryCaptured = true;
+                    sendTelemetryEvent(Telemetry.PerceivedJupyterStartupNotebook, stopWatch?.elapsedTime);
+                    const disposable = this._notebook.onSessionStatusChanged(e => {
+                        if (e === ServerStatus.Busy) {
+                            sendTelemetryEvent(Telemetry.StartExecuteNotebookCellPerceivedCold, stopWatch?.elapsedTime);
+                            disposable.dispose();
+                        }
+                    });
+                }
                 const observable = this._notebook.executeObservable(code, file, line, id, false);
 
                 // Indicate we executed some code
diff --git a/src/client/datascience/jupyter/jupyterExecution.ts b/src/client/datascience/jupyter/jupyterExecution.ts
index 3fbe3fdf1cd3..312018fdcdd8 100644
--- a/src/client/datascience/jupyter/jupyterExecution.ts
+++ b/src/client/datascience/jupyter/jupyterExecution.ts
@@ -31,6 +31,8 @@ import { JupyterWaitForIdleError } from './jupyterWaitForIdleError';
 import { KernelSelector, KernelSpecInterpreter } from './kernels/kernelSelector';
 import { NotebookStarter } from './notebookStarter';
 
+const LocalHosts = ['localhost', '127.0.0.1', '::1'];
+
 export class JupyterExecutionBase implements IJupyterExecution {
     private usablePythonInterpreter: PythonInterpreter | undefined;
     private eventEmitter: EventEmitter<void> = new EventEmitter<void>();
@@ -143,6 +145,9 @@ export class JupyterExecutionBase implements IJupyterExecution {
                 try {
                     // Start or connect to the process
                     [connection, kernelSpecInterpreter] = await Promise.all([this.startOrConnect(options, cancelToken), kernelSpecInterpreterPromise]);
+                    if (!connection.localLaunch && LocalHosts.includes(connection.hostName.toLowerCase())) {
+                        sendTelemetryEvent(Telemetry.ConnectRemoteJupyterViaLocalHost);
+                    }
                     // Create a server tha  t we will then attempt to connect to.
                     result = this.serviceContainer.get<INotebookServer>(INotebookServer);
 
diff --git a/src/client/telemetry/index.ts b/src/client/telemetry/index.ts
index c0c212d3abb2..d280af20dade 100644
--- a/src/client/telemetry/index.ts
+++ b/src/client/telemetry/index.ts
@@ -1436,6 +1436,10 @@ export interface IEventNamePropertyMapping {
     [Telemetry.ConnectFailedJupyter]: never | undefined;
     [Telemetry.ConnectLocalJupyter]: never | undefined;
     [Telemetry.ConnectRemoteJupyter]: never | undefined;
+    /**
+     * Connecting to an existing Jupyter server, but connecting to localhost.
+     */
+    [Telemetry.ConnectRemoteJupyterViaLocalHost]: never | undefined;
     [Telemetry.ConnectRemoteFailedJupyter]: never | undefined;
     [Telemetry.ConnectRemoteSelfCertFailedJupyter]: never | undefined;
     [Telemetry.RegisterAndUseInterpreterAsKernel]: never | undefined;
@@ -1469,6 +1473,14 @@ export interface IEventNamePropertyMapping {
      * If `notebook = true`, this its telemetry for native editor/notebooks.
      */
     [Telemetry.ExecuteCellPerceivedWarm]: undefined | { notebook: boolean };
+    /**
+     * Time take for jupyter server to start and be ready to run first user cell.
+     */
+    [Telemetry.PerceivedJupyterStartupNotebook]: never | undefined;
+    /**
+     * Time take for jupyter server to be busy from the time user first hit `run` cell until jupyter reports it is busy running a cell.
+     */
+    [Telemetry.StartExecuteNotebookCellPerceivedCold]: never | undefined;
     [Telemetry.ExecuteNativeCell]: never | undefined;
     [Telemetry.ExpandAll]: never | undefined;
     [Telemetry.ExportNotebook]: never | undefined;