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Hexafluoroisopropanol (HFIP) stands out as a versatile solvent in synthetic chemists' repertoire, facilitating a diverse array of intricate chemical reactions. It demonstrates a multifaceted role that extends beyond conventional uses and, in many cases, the mechanism appears to be complicated. This feature article elucidates the significance of HFIP in the context of Lewis and Brønsted acid‐catalyzed reactions with a specific emphasis on the regio‐ and stereoselective functionalization of unsaturated carbon‐carbon bonds. [ABSTRACT FROM AUTHOR]