alpha-Arylation of alpha,beta-unsaturated ketones constitutes a powerful synthetic transformation. It is most commonly achieved via cross-coupling of alpha-haloenones, but this stepwise strategy requires prefunctionalized substrates and expensive catalysts. Direct enone C-H alpha-arylation would offer an atom- and step economical alternative, but such reports are scarce. Herein we report the metal-free direct C-H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of in situ-generated beta-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O2CCF3)(2) reagents, which are readily accessed from the parent iodoarenes. The reaction is tolerant of a wide range of substitution patterns, and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled "enolonium" species and show that the presence of a beta-pyridinium moiety is critical for the desired C-C bond formation.