The stereoregularity of a polymer plays a key role in determining its properties. While stereocontrol can easily be achieved in coordination and ionic polymerization, it remains a challenge with radical polymerization. Considering the ubiquity and versatility of radical polymerization, significant efforts have been made over the past 50 years to address this issue. In this mini review, we highlight some of the strategies that have been developed to enable stereospecific radical polymerization, from the use of Lewis acid additives to the application of high electric fields. We hope that this review will provide the reader with a comprehensive overview of the current state of the art and equip them with the foundational knowledge needed to explore new avenues in this domain.