diff --git a/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts b/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts
index db53b5cf4d3..4f417c27fbf 100644
--- a/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts
+++ b/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts
@@ -30,6 +30,7 @@ import * as typeConverters from './utils/typeConverters';
 import TypingsStatus, { AtaProgressReporter } from './utils/typingsStatus';
 import * as ProjectStatus from './utils/largeProjectStatus';
 import { ActiveJsTsEditorTracker } from './utils/activeJsTsEditorTracker';
+import { LogLevelMonitor } from './utils/logLevelMonitor';
 
 // Style check diagnostics that can be reported as warnings
 const styleCheckDiagnostics = new Set([
@@ -147,6 +148,7 @@ export default class TypeScriptServiceClientHost extends Disposable {
 
 		vscode.workspace.onDidChangeConfiguration(this.configurationChanged, this, this._disposables);
 		this.configurationChanged();
+		this._register(new LogLevelMonitor(context));
 	}
 
 	private registerExtensionLanguageProvider(description: LanguageDescription, onCompletionAccepted: (item: vscode.CompletionItem) => void) {
diff --git a/extensions/typescript-language-features/src/typescriptServiceClient.ts b/extensions/typescript-language-features/src/typescriptServiceClient.ts
index c72375bd348..732851ff317 100644
--- a/extensions/typescript-language-features/src/typescriptServiceClient.ts
+++ b/extensions/typescript-language-features/src/typescriptServiceClient.ts
@@ -1055,4 +1055,3 @@ class ServerInitializingIndicator extends Disposable {
 		}
 	}
 }
-
diff --git a/extensions/typescript-language-features/src/utils/logLevelMonitor.ts b/extensions/typescript-language-features/src/utils/logLevelMonitor.ts
new file mode 100644
index 00000000000..7a3c752194e
--- /dev/null
+++ b/extensions/typescript-language-features/src/utils/logLevelMonitor.ts
@@ -0,0 +1,106 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as vscode from 'vscode';
+import { Disposable } from './dispose';
+import { localize } from '../tsServer/versionProvider';
+import { TsServerLogLevel } from './configuration';
+
+export class LogLevelMonitor extends Disposable {
+
+	private static readonly logLevelConfigKey = 'typescript.tsserver.log';
+	private static readonly logLevelChangedStorageKey = 'typescript.tsserver.logLevelChanged';
+	private static readonly doNotPromptLogLevelStorageKey = 'typescript.tsserver.doNotPromptLogLevel';
+
+	constructor(private readonly context: vscode.ExtensionContext) {
+		super();
+
+		this._register(vscode.workspace.onDidChangeConfiguration(this.onConfigurationChange, this, this._disposables));
+
+		if (this.shouldNotifyExtendedLogging()) {
+			this.notifyExtendedLogging();
+		}
+	}
+
+	private onConfigurationChange(event: vscode.ConfigurationChangeEvent) {
+		const logLevelChanged = event.affectsConfiguration(LogLevelMonitor.logLevelConfigKey);
+		if (!logLevelChanged) {
+			return;
+		}
+		this.context.globalState.update(LogLevelMonitor.logLevelChangedStorageKey, new Date());
+	}
+
+	private get logLevel(): TsServerLogLevel {
+		return TsServerLogLevel.fromString(vscode.workspace.getConfiguration().get<string>(LogLevelMonitor.logLevelConfigKey, 'off'));
+	}
+
+	/**
+	 * Last date change if it exists and can be parsed as a date,
+	 * otherwise undefined.
+	 */
+	private get lastLogLevelChange(): Date | undefined {
+		const lastChange = this.context.globalState.get<string | undefined>(LogLevelMonitor.logLevelChangedStorageKey);
+
+		if (lastChange) {
+			const date = new Date(lastChange);
+			if (date instanceof Date && !isNaN(date.valueOf())) {
+				return date;
+			}
+		}
+		return undefined;
+	}
+
+	private get doNotPrompt(): boolean {
+		return this.context.globalState.get<boolean | undefined>(LogLevelMonitor.doNotPromptLogLevelStorageKey) || false;
+	}
+
+	private shouldNotifyExtendedLogging(): boolean {
+		const lastChangeMilliseconds = this.lastLogLevelChange ? new Date(this.lastLogLevelChange).valueOf() : 0;
+		const lastChangePlusOneWeek = new Date(lastChangeMilliseconds + /* 7 days in milliseconds */ 86400000 * 7);
+
+		if (!this.doNotPrompt && this.logLevel !== TsServerLogLevel.Off && lastChangePlusOneWeek.valueOf() < Date.now()) {
+			return true;
+		}
+		return false;
+	}
+
+	private notifyExtendedLogging() {
+		const enum Choice {
+			DisableLogging = 0,
+			DoNotShowAgain = 1
+		}
+		interface Item extends vscode.MessageItem {
+			readonly choice: Choice;
+		}
+
+		vscode.window.showInformationMessage<Item>(
+			localize(
+				'typescript.extendedLogging.isEnabled',
+				"TS Server logging is currently enabled which may impact performance."),
+			{
+				title: localize(
+					'typescript.extendedLogging.disableLogging',
+					"Disable logging"),
+				choice: Choice.DisableLogging
+			},
+			{
+				title: localize(
+					'typescript.extendedLogging.doNotShowAgain',
+					"Don't show again"),
+				choice: Choice.DoNotShowAgain
+			})
+			.then(selection => {
+				if (!selection) {
+					return;
+				}
+				if (selection.choice === Choice.DisableLogging) {
+					return vscode.workspace.getConfiguration().update(LogLevelMonitor.logLevelConfigKey, 'off', true);
+				} else if (selection.choice === Choice.DoNotShowAgain) {
+					return this.context.globalState.update(LogLevelMonitor.doNotPromptLogLevelStorageKey, true);
+				}
+				return;
+			});
+	}
+}