Cyclobutanones are synthetically versatile compounds that often require extensive effort to access. Herein, we report a facile synthesis of cyclobutanones based on the C(sp3)−H insertion chemistry of oxidatively generated gold carbenes. Various cyclobutanones were obtained in synthetically useful yields from substrates with minimal structural prefunctionalization. This discovery reveals new synthetic utilities of gold‐catalyzed oxidative transformations of alkynones. Insertion into unactivated C(sp3)−H bonds by metal carbenes/carbenoids is a reaction of significant synthetic value. In this study, easily accessible alkynone substrates are converted into strained cyclobutanones through such an insertion by an oxidatively generated β‐diketone‐α‐gold carbene. This reaction serves as a benign and more synthetically expedient alternative to diazo‐based approaches.