diff --git a/src/sql/platform/telemetry/common/telemetryKeys.ts b/src/sql/platform/telemetry/common/telemetryKeys.ts
index c7783e8333..e4336b1af9 100644
--- a/src/sql/platform/telemetry/common/telemetryKeys.ts
+++ b/src/sql/platform/telemetry/common/telemetryKeys.ts
@@ -75,6 +75,7 @@ export const enum TelemetryAction {
 	DeleteAgentProxy = 'DeleteAgentProxy',
 	DeleteConnection = 'DeleteConnection',
 	DeleteServerGroup = 'DeleteServerGroup',
+	EnableTrustServerCertificate = 'EnableTrustServerCertificate',
 	FindNode = 'FindNode',
 	FirewallRuleRequested = 'FirewallRuleCreated',
 	GenerateScript = 'GenerateScript',
diff --git a/src/sql/workbench/services/connection/browser/connectionDialogService.ts b/src/sql/workbench/services/connection/browser/connectionDialogService.ts
index 8a3ec580a0..68a785131c 100644
--- a/src/sql/workbench/services/connection/browser/connectionDialogService.ts
+++ b/src/sql/workbench/services/connection/browser/connectionDialogService.ts
@@ -27,6 +27,8 @@ import * as types from 'vs/base/common/types';
 import { trim } from 'vs/base/common/strings';
 import { localize } from 'vs/nls';
 import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { IAdsTelemetryService } from 'sql/platform/telemetry/common/telemetry';
+import * as TelemetryKeys from 'sql/platform/telemetry/common/telemetryKeys';
 import { CmsConnectionController } from 'sql/workbench/services/connection/browser/cmsConnectionController';
 import { entries } from 'sql/base/common/collections';
 import { onUnexpectedError } from 'vs/base/common/errors';
@@ -89,6 +91,7 @@ export class ConnectionDialogService implements IConnectionDialogService {
 		@IClipboardService private _clipboardService: IClipboardService,
 		@ICommandService private _commandService: ICommandService,
 		@ILogService private _logService: ILogService,
+		@IAdsTelemetryService private _telemetryService: IAdsTelemetryService
 	) {
 		this.initializeConnectionProviders();
 	}
@@ -524,6 +527,7 @@ export class ConnectionDialogService implements IConnectionDialogService {
 			Note: A self-signed certificate offers only limited protection and is not a recommended practice for production environments. Do you want to enable 'Trust server certificate' on this connection and retry? `);
 			let readMoreLink = "https://learn.microsoft.com/sql/database-engine/configure-windows/enable-encrypted-connections-to-the-database-engine"
 			actions.push(new Action('trustServerCert', enableTrustServerCert, undefined, true, async () => {
+				this._telemetryService.sendActionEvent(TelemetryKeys.TelemetryView.ConnectionDialog, TelemetryKeys.TelemetryAction.EnableTrustServerCertificate);
 				this._model.options[Constants.trustServerCertificate] = true;
 				await this.handleOnConnect(this._connectionDialog.newConnectionParams, this._model as IConnectionProfile);
 				return;
diff --git a/src/sql/workbench/services/connection/test/browser/connectionDialogService.test.ts b/src/sql/workbench/services/connection/test/browser/connectionDialogService.test.ts
index 2b7d7c634c..844490c2dd 100644
--- a/src/sql/workbench/services/connection/test/browser/connectionDialogService.test.ts
+++ b/src/sql/workbench/services/connection/test/browser/connectionDialogService.test.ts
@@ -108,8 +108,10 @@ suite('ConnectionDialogService tests', () => {
 		testInstantiationService.stub(ICapabilitiesService, new TestCapabilitiesService());
 
 		let logService: ILogService = new NullLogService();
+		let telemetryService: IAdsTelemetryService = new NullAdsTelemetryService();
+
 		connectionDialogService = new ConnectionDialogService(testInstantiationService, capabilitiesService, errorMessageService.object,
-			new TestConfigurationService(), new BrowserClipboardService(layoutService, logService), NullCommandService, logService);
+			new TestConfigurationService(), new BrowserClipboardService(layoutService, logService), NullCommandService, logService, telemetryService);
 		(connectionDialogService as any)._connectionManagementService = mockConnectionManagementService.object;
 		let providerDisplayNames = ['Mock SQL Server'];
 		let providerNameToDisplayMap = { 'MSSQL': 'Mock SQL Server' };