Classic Brook rearrangements via anionic migration of silyl groups are employed extensively in the transformation of organosilicon compounds. However, radical-mediated Brook rearrangements remain underexplored. In this issue of Chem Catalysis , Shen and co-workers disclose an organophotocatalytic 1,2-Brook rearrangement to efficiently provide allyl tert -(hetero)cyclobutanols and investigate their subsequent ring-opening and -expansion functionalizations. Classic Brook rearrangements via anionic migration of silyl groups are employed extensively in the transformation of organosilicon compounds. However, radical-mediated Brook rearrangements remain underexplored. In this issue of Chem Catalysis , Shen and co-workers disclose an organophotocatalytic 1,2-Brook rearrangement to efficiently provide allyl tert -(hetero)cyclobutanols and investigate their subsequent ring-opening and -expansion functionalizations.