Reported herein is an in situ-generated hypervalent iodine-incorporating fluoroarylation of benzylidenecyclopropanes using commercially available HF·Py and aryl iodides as fluorine and aryl sources, respectively. The reaction proceeds via regioselective 1,2-fluoroiodination of a double bond followed by an iodonio-[3,3]-rearrangement of the formed cyclopropyl-I(III) species. The protocol offers facile access to valuable monofluorinated 1,1-bis-benzyl-alkenes with mild reaction conditions and moderate to good yields. The synthetic utility of the products was demonstrated by further transformations. Preliminary mechanistic studies were conducted.