diff --git a/src/vs/workbench/parts/files/electron-browser/saveErrorHandler.ts b/src/vs/workbench/parts/files/electron-browser/saveErrorHandler.ts
index 21c71d72ea6814f10bac3fe48d9108d64571db60..4512e238c9bc0f1e6b376b21c63c0c8221f641d2 100644
--- a/src/vs/workbench/parts/files/electron-browser/saveErrorHandler.ts
+++ b/src/vs/workbench/parts/files/electron-browser/saveErrorHandler.ts
@@ -174,7 +174,7 @@ export class SaveErrorHandler implements ISaveErrorHandler, IWorkbenchContributi
 
 			let errorMessage: string;
 			if (isReadonly) {
-				errorMessage = nls.localize('readonlySaveError', "Failed to save '{0}': File is write protected. Select 'Overwrite' to remove protection.", paths.basename(resource.fsPath));
+				errorMessage = nls.localize('readonlySaveError', "Failed to save '{0}': File is write protected. Select 'Overwrite' to attempt to remove protection.", paths.basename(resource.fsPath));
 			} else {
 				errorMessage = nls.localize('genericSaveError', "Failed to save '{0}': {1}", paths.basename(resource.fsPath), toErrorMessage(error, false));
 			}
diff --git a/src/vs/workbench/services/files/node/fileService.ts b/src/vs/workbench/services/files/node/fileService.ts
index 29546e8fb3d62d59fcb4db522185ffe04761766d..75a3de27e5ec617ea7e0bfcb2e4aecd27b6fe59a 100644
--- a/src/vs/workbench/services/files/node/fileService.ts
+++ b/src/vs/workbench/services/files/node/fileService.ts
@@ -918,21 +918,26 @@ export class FileService implements IFileService {
 						}
 					}
 
-					let mode = stat.mode;
-					const readonly = !(mode & 128);
-
 					// Throw if file is readonly and we are not instructed to overwrite
-					if (readonly && !options.overwriteReadonly) {
-						return TPromise.wrapError<boolean>(new FileOperationError(
-							nls.localize('fileReadOnlyError', "File is Read Only"),
-							FileOperationResult.FILE_READ_ONLY
-						));
-					}
+					if (!(stat.mode & 128) /* readonly */) {
+						if (!options.overwriteReadonly) {
+							return this.readOnlyError<boolean>();
+						}
 
-					if (readonly) {
+						// Try to change mode to writeable
+						let mode = stat.mode;
 						mode = mode | 128;
+						return pfs.chmod(absolutePath, mode).then(() => {
+
+							// Make sure to check the mode again, it could have failed
+							return pfs.stat(absolutePath).then(stat => {
+								if (!(stat.mode & 128) /* readonly */) {
+									return this.readOnlyError<boolean>();
+								}
 
-						return pfs.chmod(absolutePath, mode).then(() => exists);
+								return exists;
+							});
+						});
 					}
 
 					return TPromise.as<boolean>(exists);
@@ -943,6 +948,13 @@ export class FileService implements IFileService {
 		});
 	}
 
+	private readOnlyError<T>(): TPromise<T> {
+		return TPromise.wrapError<T>(new FileOperationError(
+			nls.localize('fileReadOnlyError', "File is Read Only"),
+			FileOperationResult.FILE_READ_ONLY
+		));
+	}
+
 	public watchFileChanges(resource: uri): void {
 		assert.ok(resource && resource.scheme === 'file', `Invalid resource for watching: ${resource}`);