In this review, we present a comprehensive update on the latest trifluoromethylation protocols for alcohols, highlighting the significant advancements and innovative strategies in this rapidly evolving field. Given the prevalence of hydroxyl groups in pharmaceutical compounds, there is a heightened interest in synthesizing functionalized organic molecules through the −CF3 functionalization of parent alcohols. Recent developments have introduced intriguing methods such as O-trifluoromethylation, dehydroxylative trifluoromethoxylation, deoxytrifluoromethylation, and oxytrifluoromethylation of readily available alcohols. These protocols enable the efficient single-step construction of diverse structures featuring C−CF3 and C−OCF3 bonds. This review aims to encapsulate the significant progress, structural diversity, and mechanistic insights of these transformative reactions, emphasizing their substrate scope and the underlying reaction pathways that drive these advancements.