diff --git a/src/client/common/persistentState.ts b/src/client/common/persistentState.ts
index 2959a2dc8216..ea86b2e145ba 100644
--- a/src/client/common/persistentState.ts
+++ b/src/client/common/persistentState.ts
@@ -108,7 +108,7 @@ export class PersistentState<T> implements IPersistentState<T> {
 export const GLOBAL_PERSISTENT_KEYS_DEPRECATED = 'PYTHON_EXTENSION_GLOBAL_STORAGE_KEYS';
 export const WORKSPACE_PERSISTENT_KEYS_DEPRECATED = 'PYTHON_EXTENSION_WORKSPACE_STORAGE_KEYS';
 
-const GLOBAL_PERSISTENT_KEYS = 'PYTHON_GLOBAL_STORAGE_KEYS';
+export const GLOBAL_PERSISTENT_KEYS = 'PYTHON_GLOBAL_STORAGE_KEYS';
 const WORKSPACE_PERSISTENT_KEYS = 'PYTHON_WORKSPACE_STORAGE_KEYS';
 type KeysStorageType = 'global' | 'workspace';
 export type KeysStorage = { key: string; defaultValue: unknown };
diff --git a/src/client/extension.ts b/src/client/extension.ts
index a4c31d91eb3b..b9f32187413b 100644
--- a/src/client/extension.ts
+++ b/src/client/extension.ts
@@ -46,6 +46,7 @@ import { WorkspaceService } from './common/application/workspace';
 import { disposeAll } from './common/utils/resourceLifecycle';
 import { ProposedExtensionAPI } from './proposedApiTypes';
 import { buildProposedApi } from './proposedApi';
+import { GLOBAL_PERSISTENT_KEYS } from './common/persistentState';
 
 durations.codeLoadingTime = stopWatch.elapsedTime;
 
@@ -62,7 +63,9 @@ export async function activate(context: IExtensionContext): Promise<PythonExtens
     let api: PythonExtension;
     let ready: Promise<void>;
     let serviceContainer: IServiceContainer;
+    let isFirstSession: boolean | undefined;
     try {
+        isFirstSession = context.globalState.get(GLOBAL_PERSISTENT_KEYS, []).length === 0;
         const workspaceService = new WorkspaceService();
         context.subscriptions.push(
             workspaceService.onDidGrantWorkspaceTrust(async () => {
@@ -79,8 +82,7 @@ export async function activate(context: IExtensionContext): Promise<PythonExtens
     }
     // Send the "success" telemetry only if activation did not fail.
     // Otherwise Telemetry is send via the error handler.
-
-    sendStartupTelemetry(ready, durations, stopWatch, serviceContainer)
+    sendStartupTelemetry(ready, durations, stopWatch, serviceContainer, isFirstSession)
         // Run in the background.
         .ignoreErrors();
     return api;
diff --git a/src/client/languageServer/watcher.ts b/src/client/languageServer/watcher.ts
index 9f12dc89df0e..39e6e0bb1ece 100644
--- a/src/client/languageServer/watcher.ts
+++ b/src/client/languageServer/watcher.ts
@@ -178,7 +178,9 @@ export class LanguageServerWatcher implements IExtensionActivationService, ILang
             // Start the language server.
             if (startupStopWatch) {
                 // It means that startup is triggering this code, track time it takes since startup to activate this code.
-                sendTelemetryEvent(EventName.LANGUAGE_SERVER_TRIGGER_DURATION, startupStopWatch.elapsedTime);
+                sendTelemetryEvent(EventName.LANGUAGE_SERVER_TRIGGER_TIME, startupStopWatch.elapsedTime, {
+                    triggerTime: startupStopWatch.elapsedTime,
+                });
             }
             await languageServerExtensionManager.startLanguageServer(lsResource, interpreter);
 
diff --git a/src/client/startupTelemetry.ts b/src/client/startupTelemetry.ts
index 43cf09c23c37..544fb24251ef 100644
--- a/src/client/startupTelemetry.ts
+++ b/src/client/startupTelemetry.ts
@@ -22,6 +22,7 @@ export async function sendStartupTelemetry(
     durations: IStartupDurations,
     stopWatch: IStopWatch,
     serviceContainer: IServiceContainer,
+    isFirstSession: boolean,
 ) {
     if (isTestExecution()) {
         return;
@@ -30,7 +31,7 @@ export async function sendStartupTelemetry(
     try {
         await activatedPromise;
         durations.totalNonBlockingActivateTime = stopWatch.elapsedTime - durations.startActivateTime;
-        const props = await getActivationTelemetryProps(serviceContainer);
+        const props = await getActivationTelemetryProps(serviceContainer, isFirstSession);
         sendTelemetryEvent(EventName.EDITOR_LOAD, durations, props);
     } catch (ex) {
         traceError('sendStartupTelemetry() failed.', ex);
@@ -76,7 +77,10 @@ export function hasUserDefinedPythonPath(resource: Resource, serviceContainer: I
         : false;
 }
 
-async function getActivationTelemetryProps(serviceContainer: IServiceContainer): Promise<EditorLoadTelemetry> {
+async function getActivationTelemetryProps(
+    serviceContainer: IServiceContainer,
+    isFirstSession?: boolean,
+): Promise<EditorLoadTelemetry> {
     // TODO: Not all of this data is showing up in the database...
 
     // TODO: If any one of these parts fails we send no info.  We should
@@ -88,7 +92,7 @@ async function getActivationTelemetryProps(serviceContainer: IServiceContainer):
     const terminalHelper = serviceContainer.get<ITerminalHelper>(ITerminalHelper);
     const terminalShellType = terminalHelper.identifyTerminalShell();
     if (!workspaceService.isTrusted) {
-        return { workspaceFolderCount, terminal: terminalShellType };
+        return { workspaceFolderCount, terminal: terminalShellType, isFirstSession };
     }
     const interpreterService = serviceContainer.get<IInterpreterService>(IInterpreterService);
     const mainWorkspaceUri = workspaceService.workspaceFolders?.length
@@ -132,5 +136,6 @@ async function getActivationTelemetryProps(serviceContainer: IServiceContainer):
         usingUserDefinedInterpreter,
         usingGlobalInterpreter,
         appName,
+        isFirstSession,
     };
 }
diff --git a/src/client/telemetry/constants.ts b/src/client/telemetry/constants.ts
index 3321653c3bd7..b405143c0ba3 100644
--- a/src/client/telemetry/constants.ts
+++ b/src/client/telemetry/constants.ts
@@ -64,7 +64,7 @@ export enum EventName {
     EXTENSION_SURVEY_PROMPT = 'EXTENSION_SURVEY_PROMPT',
 
     LANGUAGE_SERVER_ENABLED = 'LANGUAGE_SERVER.ENABLED',
-    LANGUAGE_SERVER_TRIGGER_DURATION = 'LANGUAGE_SERVER.TRIGGER_DURATION',
+    LANGUAGE_SERVER_TRIGGER_TIME = 'LANGUAGE_SERVER_TRIGGER_TIME',
     LANGUAGE_SERVER_STARTUP = 'LANGUAGE_SERVER.STARTUP',
     LANGUAGE_SERVER_READY = 'LANGUAGE_SERVER.READY',
     LANGUAGE_SERVER_TELEMETRY = 'LANGUAGE_SERVER.EVENT',
diff --git a/src/client/telemetry/index.ts b/src/client/telemetry/index.ts
index b2ed37939fa9..bb2cd6d77896 100644
--- a/src/client/telemetry/index.ts
+++ b/src/client/telemetry/index.ts
@@ -723,6 +723,11 @@ export interface IEventNamePropertyMapping {
          * If global interpreter is being used
          */
         usingGlobalInterpreter?: boolean;
+        /**
+         * Carries `true` if it is the very first session of the user. We check whether persistent cache is empty
+         * to approximately guess if it's the first session.
+         */
+        isFirstSession?: boolean;
     };
     /**
      * Telemetry event sent when substituting Environment variables to calculate value of variables
@@ -1329,11 +1334,17 @@ export interface IEventNamePropertyMapping {
      * Track how long it takes to trigger language server activation code, after Python extension starts activating.
      */
     /* __GDPR__
-       "language_server_trigger_duration" : {
-          "duration" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "owner": "karrtikr", "isMeasurement": true }
+       "language_server_trigger_time" : {
+          "duration" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true, "owner": "karrtikr" },
+          "triggerTime" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true, "owner": "karrtikr" }
        }
      */
-    [EventName.LANGUAGE_SERVER_TRIGGER_DURATION]: unknown;
+    [EventName.LANGUAGE_SERVER_TRIGGER_TIME]: {
+        /**
+         * Time it took to trigger language server startup.
+         */
+        triggerTime: number;
+    };
     /**
      * Telemetry event sent when starting Node.js server
      */