Sulfoxides have emerged as pivotal constituents in modern carbohydrate chemistry. As anomeric leaving groups, sulfinyl moieties may occupy positions directly at the anomeric position or at a more remote site. This feature article is focused on the evolution and notable advancements of glycosyl sulfoxide donors in glycosylation reactions. Its objective is to elucidate the obstacles and prospects within this evolving research domain, with the aim of enhancing comprehension and progress in the field of carbohydrate chemistry.