diff --git a/news/3 Code Health/7332.md b/news/3 Code Health/7332.md
new file mode 100644
index 000000000000..2724b77181e7
--- /dev/null
+++ b/news/3 Code Health/7332.md	
@@ -0,0 +1 @@
+Add telemetry to measure debugger start up performance.
diff --git a/src/client/datascience/debugLocationTracker.ts b/src/client/datascience/debugLocationTracker.ts
index 187a54bffd8c..387475245836 100644
--- a/src/client/datascience/debugLocationTracker.ts
+++ b/src/client/datascience/debugLocationTracker.ts
@@ -5,6 +5,10 @@ import { injectable } from 'inversify';
 import { DebugSession, Event, EventEmitter } from 'vscode';
 import { DebugProtocol } from 'vscode-debugprotocol';
 
+import { StopWatch } from '../common/utils/stopWatch';
+import { AttachRequestArguments, ConsoleType, LaunchRequestArguments, TriggerType } from '../debugger/types';
+import { sendTelemetryEvent } from '../telemetry';
+import { EventName } from '../telemetry/constants';
 import { IDebugLocation, IDebugLocationTracker } from './types';
 
 // When a python debugging session is active keep track of the current debug location
@@ -13,10 +17,16 @@ export class DebugLocationTracker implements IDebugLocationTracker {
     private waitingForStackTrace: boolean = false;
     private _debugLocation: IDebugLocation | undefined;
     private debugLocationUpdatedEvent: EventEmitter<void> = new EventEmitter<void>();
+    private trigger: TriggerType = 'launch';
+    private console: ConsoleType | undefined;
+    private timer = new StopWatch();
 
-    public setDebugSession(_targetSession: DebugSession) {
+    public setDebugSession(targetSession: DebugSession) {
         this.DebugLocation = undefined;
         this.waitingForStackTrace = false;
+        this.trigger = targetSession.configuration.type as TriggerType;
+        const debugConfiguration = targetSession.configuration as Partial<LaunchRequestArguments & AttachRequestArguments>;
+        this.console = debugConfiguration.console;
     }
 
     public get debugLocationUpdated(): Event<void> {
@@ -27,8 +37,20 @@ export class DebugLocationTracker implements IDebugLocationTracker {
         return this._debugLocation;
     }
 
+    public onWillStartSession() {
+        this.sendTelemetry(EventName.DEBUG_SESSION_START);
+    }
+
     // tslint:disable-next-line:no-any
     public onDidSendMessage(message: DebugProtocol.ProtocolMessage) {
+        if (message.type === 'response') {
+            const response = message as DebugProtocol.Response;
+            if (response.command === 'configurationDone') {
+                // "configurationDone" response is sent immediately after user code starts running.
+                this.sendTelemetry(EventName.DEBUG_SESSION_USER_CODE_RUNNING);
+            }
+        }
+
         if (this.isStopEvent(message)) {
             // Some type of stop, wait to see our next stack trace to find our location
             this.waitingForStackTrace = true;
@@ -51,6 +73,14 @@ export class DebugLocationTracker implements IDebugLocationTracker {
 
     }
 
+    public onWillStopSession() {
+        this.sendTelemetry(EventName.DEBUG_SESSION_STOP);
+    }
+
+    public onError?(_error: Error) {
+        this.sendTelemetry(EventName.DEBUG_SESSION_ERROR);
+    }
+
     // Set our new location and fire our debug event
     private set DebugLocation(newLocation: IDebugLocation | undefined) {
         const oldLocation = this._debugLocation;
@@ -116,4 +146,15 @@ export class DebugLocationTracker implements IDebugLocationTracker {
 
         return false;
     }
+
+    private sendTelemetry(eventName: EventName) {
+        if (eventName === EventName.DEBUG_SESSION_START) {
+            this.timer.reset();
+        }
+        const telemetryProps = {
+            trigger: this.trigger,
+            console: this.console
+        };
+        sendTelemetryEvent(eventName, this.timer.elapsedTime, telemetryProps);
+    }
 }
diff --git a/src/client/debugger/types.ts b/src/client/debugger/types.ts
index 1241988c1f61..b2675f9082d6 100644
--- a/src/client/debugger/types.ts
+++ b/src/client/debugger/types.ts
@@ -82,3 +82,5 @@ export interface AttachRequestArguments extends DebugProtocol.AttachRequestArgum
 export interface DebugConfigurationArguments extends LaunchRequestArguments, AttachRequestArguments { }
 
 export type ConsoleType = 'internalConsole' | 'integratedTerminal' | 'externalTerminal';
+
+export type TriggerType = 'launch' | 'attach' | 'test';
diff --git a/src/client/telemetry/constants.ts b/src/client/telemetry/constants.ts
index 8b97329d0b32..51e8d25c02f1 100644
--- a/src/client/telemetry/constants.ts
+++ b/src/client/telemetry/constants.ts
@@ -38,6 +38,10 @@ export enum EventName {
     WORKSPACE_SYMBOLS_GO_TO = 'WORKSPACE_SYMBOLS.GO_TO',
     EXECUTION_CODE = 'EXECUTION_CODE',
     EXECUTION_DJANGO = 'EXECUTION_DJANGO',
+    DEBUG_SESSION_ERROR = 'DEBUG_SESSION.ERROR',
+    DEBUG_SESSION_START = 'DEBUG_SESSION.START',
+    DEBUG_SESSION_STOP = 'DEBUG_SESSION.STOP',
+    DEBUG_SESSION_USER_CODE_RUNNING = 'DEBUG_SESSION.USER_CODE_RUNNING',
     DEBUGGER = 'DEBUGGER',
     DEBUGGER_ATTACH_TO_CHILD_PROCESS = 'DEBUGGER.ATTACH_TO_CHILD_PROCESS',
     DEBUGGER_CONFIGURATION_PROMPTS = 'DEBUGGER.CONFIGURATION.PROMPTS',
diff --git a/src/client/telemetry/index.ts b/src/client/telemetry/index.ts
index 0e07984ecb69..d185c264c67c 100644
--- a/src/client/telemetry/index.ts
+++ b/src/client/telemetry/index.ts
@@ -15,7 +15,7 @@ import { TerminalShellType } from '../common/terminal/types';
 import { StopWatch } from '../common/utils/stopWatch';
 import { Telemetry } from '../datascience/constants';
 import { DebugConfigurationType } from '../debugger/extension/types';
-import { ConsoleType } from '../debugger/types';
+import { ConsoleType, TriggerType } from '../debugger/types';
 import { AutoSelectionRule } from '../interpreter/autoSelection/types';
 import { InterpreterType } from '../interpreter/contracts';
 import { LinterId } from '../linters/types';
@@ -267,6 +267,98 @@ export interface IEventNamePropertyMapping {
          */
         enabled: boolean;
     };
+    /**
+     * Telemetry captured before starting debug session.
+     */
+    [EventName.DEBUG_SESSION_START]: {
+        /**
+         * Trigger for starting the debugger.
+         * - `launch`: Launch/start new code and debug it.
+         * - `attach`: Attach to an exiting python process (remote debugging).
+         * - `test`: Debugging python tests.
+         *
+         * @type {TriggerType}
+         */
+        trigger: TriggerType;
+        /**
+         * Type of console used.
+         *  -`internalConsole`: Use VS Code debug console (no shells/terminals).
+         * - `integratedTerminal`: Use VS Code terminal.
+         * - `externalTerminal`: Use an External terminal.
+         *
+         * @type {ConsoleType}
+         */
+        console?: ConsoleType;
+    };
+    /**
+     * Telemetry captured when debug session runs into an error.
+     */
+    [EventName.DEBUG_SESSION_ERROR]: {
+        /**
+         * Trigger for starting the debugger.
+         * - `launch`: Launch/start new code and debug it.
+         * - `attach`: Attach to an exiting python process (remote debugging).
+         * - `test`: Debugging python tests.
+         *
+         * @type {TriggerType}
+         */
+        trigger: TriggerType;
+        /**
+         * Type of console used.
+         *  -`internalConsole`: Use VS Code debug console (no shells/terminals).
+         * - `integratedTerminal`: Use VS Code terminal.
+         * - `externalTerminal`: Use an External terminal.
+         *
+         * @type {ConsoleType}
+         */
+        console?: ConsoleType;
+    };
+    /**
+     * Telemetry captured after stopping debug session.
+     */
+    [EventName.DEBUG_SESSION_STOP]: {
+        /**
+         * Trigger for starting the debugger.
+         * - `launch`: Launch/start new code and debug it.
+         * - `attach`: Attach to an exiting python process (remote debugging).
+         * - `test`: Debugging python tests.
+         *
+         * @type {TriggerType}
+         */
+        trigger: TriggerType;
+        /**
+         * Type of console used.
+         *  -`internalConsole`: Use VS Code debug console (no shells/terminals).
+         * - `integratedTerminal`: Use VS Code terminal.
+         * - `externalTerminal`: Use an External terminal.
+         *
+         * @type {ConsoleType}
+         */
+        console?: ConsoleType;
+    };
+    /**
+     * Telemetry captured when user code starts running after loading the debugger.
+     */
+    [EventName.DEBUG_SESSION_USER_CODE_RUNNING]: {
+        /**
+         * Trigger for starting the debugger.
+         * - `launch`: Launch/start new code and debug it.
+         * - `attach`: Attach to an exiting python process (remote debugging).
+         * - `test`: Debugging python tests.
+         *
+         * @type {TriggerType}
+         */
+        trigger: TriggerType;
+        /**
+         * Type of console used.
+         *  -`internalConsole`: Use VS Code debug console (no shells/terminals).
+         * - `integratedTerminal`: Use VS Code terminal.
+         * - `externalTerminal`: Use an External terminal.
+         *
+         * @type {ConsoleType}
+         */
+        console?: ConsoleType;
+    };
     /**
      * Telemetry captured when starting the debugger.
      */
@@ -277,9 +369,9 @@ export interface IEventNamePropertyMapping {
          * - `attach`: Attach to an exiting python process (remote debugging).
          * - `test`: Debugging python tests.
          *
-         * @type {('launch' | 'attach' | 'test')}
+         * @type {TriggerType}
          */
-        trigger: 'launch' | 'attach' | 'test';
+        trigger: TriggerType;
         /**
          * Type of console used.
          *  -`internalConsole`: Use VS Code debug console (no shells/terminals).