diff --git a/src/vs/workbench/contrib/files/browser/fileCommands.ts b/src/vs/workbench/contrib/files/browser/fileCommands.ts
index d834b54f85aaa..7a57e7ccb92e4 100644
--- a/src/vs/workbench/contrib/files/browser/fileCommands.ts
+++ b/src/vs/workbench/contrib/files/browser/fileCommands.ts
@@ -275,7 +275,14 @@ CommandsRegistry.registerCommand({
 async function resourcesToClipboard(resources: URI[], relative: boolean, clipboardService: IClipboardService, labelService: ILabelService, configurationService: IConfigurationService): Promise<void> {
 	if (resources.length) {
 		const lineDelimiter = isWindows ? '\r\n' : '\n';
-		const separator = relative ? configurationService.getValue<'/' | '\\' | undefined>('explorer.copyRelativePathSeparator') : undefined;
+
+		let separator: '/' | '\\' | undefined = undefined;
+		if (relative) {
+			const relativeSeparator = configurationService.getValue('explorer.copyRelativePathSeparator');
+			if (relativeSeparator === '/' || relativeSeparator === '\\') {
+				separator = relativeSeparator;
+			}
+		}
 
 		const text = resources.map(resource => labelService.getUriLabel(resource, { relative, noPrefix: true, separator })).join(lineDelimiter);
 		await clipboardService.writeText(text);
diff --git a/src/vs/workbench/contrib/files/browser/files.contribution.ts b/src/vs/workbench/contrib/files/browser/files.contribution.ts
index 6b5c655053128..6e87acfd99b1b 100644
--- a/src/vs/workbench/contrib/files/browser/files.contribution.ts
+++ b/src/vs/workbench/contrib/files/browser/files.contribution.ts
@@ -407,13 +407,16 @@ configurationRegistry.registerConfiguration({
 			'type': 'string',
 			'enum': [
 				'/',
-				'\\'
+				'\\',
+				'auto'
 			],
 			'enumDescriptions': [
 				nls.localize('copyRelativePathSeparator.slash', "Use slash as path separation character."),
 				nls.localize('copyRelativePathSeparator.backslash', "Use backslash as path separation character."),
+				nls.localize('copyRelativePathSeparator.auto', "Uses operating system specific path separation character."),
 			],
-			'description': nls.localize('copyRelativePathSeparator', "The path separation character used when copying relative file paths. Will use the operating system default unless specified."),
+			'description': nls.localize('copyRelativePathSeparator', "The path separation character used when copying relative file paths."),
+			'default': 'auto'
 		}
 	}
 });