A hypervalent iodine(III)-mediated ring-contractive fluorination reaction of 2-alkylidenecyclobutanol derivatives is presented. The protocol allows the facile synthesis of β-monofluorinated cyclopropanecarbaldehydes via a fluorination/semipinacol rearrangement cascade using nucleophilic Py·HF as the fluorine source. For challenging electron-rich arene substrates, the installation of a protecting group on the free alcohol is pivotal for maintaining the reaction efficiency. The synthetic utility was demonstrated by the scalability of this reaction and further transformations of the products.