Recent years have witnessed a renaissance of radical cross-coupling of cycloketone oximes which served as active cyanoalkyl radical via ring fragmentation in various transformations. It provided an efficient and practical strategy to introduce cyanoalkyl groups into organic compounds without using toxic cyanide sources. In this review, a comprehensive overview of recent advances in the field of redox-active cycloketone oximes-based cross-couplings were covered. This review was categorized into two broad parts: non-photocatalyzed and photocatalyzed cross-couplings according to the reaction cond...