We report a photoinduced iron catalysis for the efficient C–C bond cleavage and bromination or iodination of unstrained tertiary cycloalkanols with NBS/NIS. The reaction features good functional group tolerance and high yields under mild conditions and provides a powerful tool for the preparation of remote halogenated alkyl ketones. The products can be converted via nucleophilic substitution or cross-coupling to other valuable molecules, such as haloperidol, fluanisone, and azabuperone, demonstrating the synthetic value of this reaction.