diff --git a/src/vs/workbench/electron-browser/main.contribution.ts b/src/vs/workbench/electron-browser/main.contribution.ts
index 882095b2680..50daffa2ecd 100644
--- a/src/vs/workbench/electron-browser/main.contribution.ts
+++ b/src/vs/workbench/electron-browser/main.contribution.ts
@@ -47,10 +47,10 @@ configurationRegistry.registerConfiguration({
 	'title': nls.localize('windowConfigurationTitle', "Window configuration"),
 	'type': 'object',
 	'properties': {
-		'window.openInNewWindow': {
+		'window.openFilesInNewWindow': {
 			'type': 'boolean',
 			'default': true,
-			'description': nls.localize('openInNewWindow', "When enabled, will open files in a new window instead of reusing an existing instance.")
+			'description': nls.localize('openFilesInNewWindow', "When enabled, will open files in a new window instead of reusing an existing instance.")
 		},
 		'window.reopenFolders': {
 			'type': 'string',
diff --git a/src/vs/workbench/electron-main/windows.ts b/src/vs/workbench/electron-main/windows.ts
index bd1526c97ca..5a829094fc7 100644
--- a/src/vs/workbench/electron-main/windows.ts
+++ b/src/vs/workbench/electron-main/windows.ts
@@ -369,8 +369,12 @@ export class WindowsManager {
 
 			// Let the user settings override how files are open in a new window or same window
 			let openFilesInNewWindow = openConfig.forceNewWindow;
-			if (openFilesInNewWindow && !openConfig.cli.pluginDevelopmentPath) {
-				openFilesInNewWindow = settings.manager.getValue('window.openInNewWindow', openFilesInNewWindow); // can be overriden via settings (not for PDE though!)
+			if (openFilesInNewWindow && !openConfig.cli.pluginDevelopmentPath) { // can be overriden via settings (not for PDE though!)
+				if (settings.manager.getValue('window.openInNewWindow', null) !== null) {
+					openFilesInNewWindow = settings.manager.getValue('window.openInNewWindow', openFilesInNewWindow); // TODO@Ben remove legacy setting in a couple of versions
+				} else {
+					openFilesInNewWindow = settings.manager.getValue('window.openFilesInNewWindow', openFilesInNewWindow);
+				}
 			}
 
 			// Open Files in last instance if any and flag tells us so