diff --git a/extensions/typescript/src/typescriptMain.ts b/extensions/typescript/src/typescriptMain.ts
index 7bc9120c593..f633472ab55 100644
--- a/extensions/typescript/src/typescriptMain.ts
+++ b/extensions/typescript/src/typescriptMain.ts
@@ -443,6 +443,15 @@ class TypeScriptServiceClientHost implements ITypescriptServiceClientHost {
 		return this.client;
 	}
 
+	public restartTsServer(): void {
+		this.client.restartTsServer();
+		if (this.languages) {
+			for (const provider of this.languages) {
+				provider.reInitialize();
+			}
+		}
+	}
+
 	public reloadProjects(): void {
 		this.client.execute('reloadProjects', null, false);
 		this.triggerAllDiagnostics();
diff --git a/extensions/typescript/src/typescriptServiceClient.ts b/extensions/typescript/src/typescriptServiceClient.ts
index 1dc21e9e2b0..3ff2915ab41 100644
--- a/extensions/typescript/src/typescriptServiceClient.ts
+++ b/extensions/typescript/src/typescriptServiceClient.ts
@@ -144,7 +144,7 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 	private _output: OutputChannel;
 	private tsServerLogFile: string | null = null;
 	private tsServerLogLevel: TsServerLogLevel = TsServerLogLevel.Off;
-	private servicePromise: Promise<cp.ChildProcess> | null;
+	private servicePromise: Thenable<cp.ChildProcess> | null;
 	private lastError: Error | null;
 	private reader: Reader<Proto.Response>;
 	private sequenceNumber: number;
@@ -211,21 +211,8 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 
 			if (this.servicePromise === null && (oldglobalTsdk !== this.globalTsdk || oldLocalTsdk !== this.localTsdk)) {
 				this.startService();
-			} else if (this.servicePromise !== null && this.tsServerLogLevel !== oldLoggingLevel) {
-
-				const reloadItem = { title: localize('reloadTitle', 'Reload') };
-				window.showInformationMessage<MessageItem>(
-					localize('tsserverLogReloadBlurb', 'Reload VS Code to apply \'typescript.tsserver.log\' change'),
-					reloadItem,
-					{
-						title: localize('later', 'Later'),
-						isCloseAffordance: true
-					})
-					.then(selected => {
-						if (selected === reloadItem) {
-							commands.executeCommand('workbench.action.reloadWindow');
-						}
-					});
+			} else if (this.servicePromise !== null && (this.tsServerLogLevel !== oldLoggingLevel || (oldglobalTsdk !== this.globalTsdk || oldLocalTsdk !== this.localTsdk))) {
+				this.promptUserToRestartTsServer();
 			}
 		}));
 		if (this.packageInfo && this.packageInfo.aiKey) {
@@ -235,6 +222,41 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 		this.startService();
 	}
 
+	public restartTsServer(): void {
+		const start = () => {
+			this.trace = this.readTrace();
+			this.tsServerLogLevel = this.readTsServerLogLevel();
+			this.servicePromise = this.startService();
+			return this.servicePromise;
+		};
+
+		if (this.servicePromise !== null) {
+			this.servicePromise = this.servicePromise.then(cp => {
+				if (cp) {
+					cp.kill();
+				}
+			}).then(start);
+		} else {
+			start();
+		}
+	}
+
+	private promptUserToRestartTsServer(): void {
+		const restartItem = { title: localize('restartTsServerTitle', 'Restart') };
+		window.showInformationMessage<MessageItem>(
+			localize('restartTypeScriptServerBlurb', 'Restart TypeScript Server to apply change'),
+			restartItem,
+			{
+				title: localize('later', 'Later'),
+				isCloseAffordance: true
+			})
+			.then(selected => {
+				if (selected === restartItem) {
+					this.restartTsServer();
+				}
+			});
+	}
+
 	private extractGlobalTsdk(configuration: WorkspaceConfiguration): string | null {
 		let inspect = configuration.inspect('typescript.tsdk');
 		if (inspect && inspect.globalValue && 'string' === typeof inspect.globalValue) {
@@ -382,7 +404,7 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 		}
 	}
 
-	private service(): Promise<cp.ChildProcess> {
+	private service(): Thenable<cp.ChildProcess> {
 		if (this.servicePromise) {
 			return this.servicePromise;
 		}
@@ -441,7 +463,7 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 		return !!this.localTsdk;
 	}
 
-	private startService(resendModels: boolean = false): void {
+	private startService(resendModels: boolean = false): Thenable<cp.ChildProcess> {
 		let modulePath: Thenable<string> = Promise.resolve(this.globalTypescriptPath);
 
 		if (!this.workspaceState.get<boolean>(TypeScriptServiceClient.tsdkMigratedStorageKey, false)) {
@@ -451,7 +473,7 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 			}
 		}
 
-		modulePath.then(modulePath => {
+		return modulePath.then(modulePath => {
 			if (this.workspaceState.get<boolean>(TypeScriptServiceClient.useWorkspaceTsdkStorageKey, false)) {
 				if (workspace.rootPath) {
 					// TODO: check if we need better error handling
@@ -460,7 +482,7 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 			}
 			return modulePath;
 		}).then(modulePath => {
-			this.servicePromise = new Promise<cp.ChildProcess>((resolve, reject) => {
+			return this.servicePromise = new Promise<cp.ChildProcess>((resolve, reject) => {
 				const tsConfig = workspace.getConfiguration('typescript');
 
 				this.info(`Using tsserver from location: ${modulePath}`);
@@ -618,20 +640,7 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 			if (firstRun || newModulePath === this.modulePath) {
 				return;
 			}
-
-			const reloadMessage = { title: localize('reloadTitle', 'Reload') };
-			window.showInformationMessage<MessageItem>(
-				localize('reloadBlurb', 'Reload window to apply changes'),
-				reloadMessage,
-				{
-					title: localize('later', 'Later'),
-					isCloseAffordance: true
-				})
-				.then(selected => {
-					if (selected === reloadMessage) {
-						commands.executeCommand('workbench.action.reloadWindow');
-					}
-				});
+			this.promptUserToRestartTsServer();
 		};
 
 		return window.showQuickPick<MyQuickPickItem>(pickOptions, {
@@ -681,16 +690,16 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 			return window.showErrorMessage<MessageItem>(
 				localize(
 					'typescript.openTsServerLog.loggingNotEnabled',
-					'TS Server logging is off. Please set `typescript.tsserver.log` and reload VS Code to enable logging'),
+					'TS Server logging is off. Please set `typescript.tsserver.log` and restart the TS server to enable logging'),
 				{
 					title: localize(
 						'typescript.openTsServerLog.enableAndReloadOption',
-						'Enable logging and reload VS Code'),
+						'Enable logging and restart TS server'),
 				})
 				.then(selection => {
 					if (selection) {
 						return workspace.getConfiguration().update('typescript.tsserver.log', 'verbose', true).then(() => {
-							commands.executeCommand('workbench.action.reloadWindow');
+							this.restartTsServer();
 							return false;
 						});
 					}
@@ -916,16 +925,17 @@ export default class TypeScriptServiceClient implements ITypescriptServiceClient
 			this.callbacks[serverRequest.seq] = requestItem.callbacks;
 			this.pendingResponses++;
 		}
-		this.service().then((childProcess) => {
-			childProcess.stdin.write(JSON.stringify(serverRequest) + '\r\n', 'utf8');
-		}).catch(err => {
-			let callback = this.callbacks[serverRequest.seq];
-			if (callback) {
-				callback.e(err);
-				delete this.callbacks[serverRequest.seq];
-				this.pendingResponses--;
-			}
-		});
+		this.service()
+			.then((childProcess) => {
+				childProcess.stdin.write(JSON.stringify(serverRequest) + '\r\n', 'utf8');
+			}).then(undefined, err => {
+				let callback = this.callbacks[serverRequest.seq];
+				if (callback) {
+					callback.e(err);
+					delete this.callbacks[serverRequest.seq];
+					this.pendingResponses--;
+				}
+			});
 	}
 
 	private tryCancelRequest(seq: number): boolean {