const string BrochureDirectory = "~/Brochures/"; string brochurePath = BrochureDirectory + BrochureUpload.FileName; string fileNameWithoutExtension = System.IO.Path.GetFileNameWithoutExtension(BrochureUpload.FileName); int iteration = 1; while (System.IO.File.Exists(Server.MapPath(brochurePath))) { brochurePath = string.Concat(BrochureDirectory, fileNameWithoutExtension, "-", iteration, ".pdf"); iteration++; }