diff --git a/src/vs/workbench/contrib/tasks/electron-browser/task.contribution.ts b/src/vs/workbench/contrib/tasks/electron-browser/task.contribution.ts
index 688ffaf6fe8..03ab2edd62d 100644
--- a/src/vs/workbench/contrib/tasks/electron-browser/task.contribution.ts
+++ b/src/vs/workbench/contrib/tasks/electron-browser/task.contribution.ts
@@ -1360,6 +1360,7 @@ class TaskService extends Disposable implements ITaskService {
 				this.modelService, this.configurationResolverService, this.telemetryService,
 				this.contextService, this._environmentService,
 				TaskService.OutputChannelId,
+				this.configurationService,
 				(workspaceFolder: IWorkspaceFolder) => {
 					if (!workspaceFolder) {
 						return undefined;
@@ -2736,6 +2737,7 @@ let schema: IJSONSchema = {
 
 import schemaVersion1 from '../common/jsonSchema_v1';
 import schemaVersion2, { updateProblemMatchers } from '../common/jsonSchema_v2';
+import { IConfigurationRegistry, Extensions } from 'vs/platform/configuration/common/configurationRegistry';
 schema.definitions = {
 	...schemaVersion1.definitions,
 	...schemaVersion2.definitions,
@@ -2749,3 +2751,19 @@ ProblemMatcherRegistry.onMatcherChanged(() => {
 	updateProblemMatchers();
 	jsonRegistry.notifySchemaChanged(schemaId);
 });
+
+const configurationRegistry = Registry.as<IConfigurationRegistry>(Extensions.Configuration);
+configurationRegistry.registerConfiguration({
+	id: 'Tasks',
+	order: 100,
+	title: nls.localize('tasksConfigurationTitle', "Tasks"),
+	type: 'object',
+	properties: {
+		'tasks.terminal.windowsUseWinpty': {
+			markdownDescription: nls.localize('tasks.terminal.windowsUseWinpty', "Takes precedent over all other pty settings and forces the integrated terminal to use Winpty instead of Conpty."),
+			type: 'boolean',
+			default: true
+		}
+	}
+});
+
diff --git a/src/vs/workbench/contrib/tasks/electron-browser/terminalTaskSystem.ts b/src/vs/workbench/contrib/tasks/electron-browser/terminalTaskSystem.ts
index b0302bd3d23..0dad2c99818 100644
--- a/src/vs/workbench/contrib/tasks/electron-browser/terminalTaskSystem.ts
+++ b/src/vs/workbench/contrib/tasks/electron-browser/terminalTaskSystem.ts
@@ -44,6 +44,7 @@ import { IWorkbenchEnvironmentService } from 'vs/workbench/services/environment/
 import { Schemas } from 'vs/base/common/network';
 import { getWindowsBuildNumber } from 'vs/workbench/contrib/terminal/node/terminal';
 import { IPanelService } from 'vs/workbench/services/panel/common/panelService';
+import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
 
 interface TerminalData {
 	terminal: ITerminalInstance;
@@ -171,7 +172,8 @@ export class TerminalTaskSystem implements ITaskSystem {
 		private contextService: IWorkspaceContextService,
 		private environmentService: IWorkbenchEnvironmentService,
 		private outputChannelId: string,
-		taskSystemInfoResolver: TaskSystemInfoResovler
+		private readonly configurationService: IConfigurationService,
+		taskSystemInfoResolver: TaskSystemInfoResovler,
 	) {
 
 		this.activeTasks = Object.create(null);
@@ -877,6 +879,9 @@ export class TerminalTaskSystem implements ITaskSystem {
 		if (options.env) {
 			shellLaunchConfig.env = options.env;
 		}
+
+		// Conpty doesn't do linefeeds in an expected way. Force winpty unless the user has requested otherwise.
+		shellLaunchConfig.forceWinpty = this.configurationService.getValue('tasks.terminal.windowsUseWinpty');
 		return shellLaunchConfig;
 	}
 
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
index 7bcf1281bdd..5180ade91ae 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
@@ -182,7 +182,8 @@ export class TerminalProcessManager implements ITerminalProcessManager {
 		const env = terminalEnvironment.createTerminalEnvironment(shellLaunchConfig, lastActiveWorkspace, envFromConfigValue, this._configurationResolverService, isWorkspaceShellAllowed, this._productService.version, this._configHelper.config.setLocaleVariables);
 
 		this._logService.debug(`Terminal process launching`, shellLaunchConfig, initialCwd, cols, rows, env);
-		return this._terminalInstanceService.createTerminalProcess(shellLaunchConfig, initialCwd, cols, rows, env, this._configHelper.config.windowsEnableConpty);
+		const useConpty = (shellLaunchConfig.forceWinpty !== true) && this._configHelper.config.windowsEnableConpty;
+		return this._terminalInstanceService.createTerminalProcess(shellLaunchConfig, initialCwd, cols, rows, env, useConpty);
 	}
 
 	public setDimensions(cols: number, rows: number): void {
diff --git a/src/vs/workbench/contrib/terminal/common/terminal.ts b/src/vs/workbench/contrib/terminal/common/terminal.ts
index a1932f39345..94acb510847 100644
--- a/src/vs/workbench/contrib/terminal/common/terminal.ts
+++ b/src/vs/workbench/contrib/terminal/common/terminal.ts
@@ -192,6 +192,12 @@ export interface IShellLaunchConfig {
 	 * provided as nothing will be inherited from the process or any configuration.
 	 */
 	strictEnv?: boolean;
+
+	/**
+	 * Moving forward, conpty will be the default. However, there are cases where conpty is not ready
+	 * do be the default. This property will force winpty to be uses, even when conpty would normally be used.
+	 */
+	forceWinpty?: boolean;
 }
 
 export interface ITerminalService {