diff --git a/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts b/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
index e159b9591ed1ff6e37e46798ec7a8561c9b4cd91..26350c27196f40b7fae7b1b283b1aa766cdcbcaa 100644
--- a/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
+++ b/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
@@ -765,6 +765,9 @@ export class SimpleFileDialog {
 				// File or folder doesn't exist
 				this.filePickBox.validationMessage = nls.localize('remoteFileDialog.validateNonexistentDir', 'Please enter a path that exists.');
 				return Promise.resolve(false);
+			} else if (uri.path === '/' && (await this.isWindowsOS())) {
+				this.filePickBox.validationMessage = nls.localize('remoteFileDialog.windowsDriveLetter', 'Please start the path with a drive letter.');
+				return Promise.resolve(false);
 			} else if (stat.isDirectory && !this.allowFolderSelection) {
 				// Folder selected when folder selection not permitted
 				this.filePickBox.validationMessage = nls.localize('remoteFileDialog.validateFileOnly', 'Please select a file.');