A novel and practical palladium-catalyzed aerobic oxyarylthiolation of alkynone O-methyloximes for the assembly of 4-sulfenylisoxazole derivatives using S₈ and arylhydrazines as the S-aryl sources is accomplished. In the presence of 0.1 mol% of IPr–Pd–allyl–Cl as the catalyst and O₂ (1 atm) as the sole oxidant, both alkynone O-methyloximes and arylhydrazines are suitable substrates, delivering diverse 4-sulfenyl isoxazoles in moderate to good yields with good functional group tolerance. Notably, the phenyl diazonium salt and sodium phenyl sulfinate are also suitable arylation reagents, providing an alternative synthetic strategy to access structurally diverse 4-sulfenyl isoxazoles.