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Abstract Poly(α-hydroxy acids), as a family of biodegradable polyesters, are valuable materials due to their broad applications in packaging, agriculture, and biomedical engineering. Herein we highlight and explore recent advances of catalysts in controlled ring-opening polymerization of O-carboxyanhydrides towards functionalized poly(α-hydroxy acids), especially metal catalyst-mediated controlled polymerization. Limitations of current polymerization strategies of O-carboxyanhydrides are discussed. Introduction Organocatalysts for O-Carboxyanhydride Polymerization Metal Catalysts for O-Carboxyanhydride Polymerization Stereoselective and Stereosequence-Controlled Polymerization of O-Carboxyanhydrides Conclusions and Outlook