The Wacker-type aminocarbonylation of unsaturated amides shows distinctive dependence of reactivity on the reaction medium: endo nitrogen nucleophiles (endo-carbamates 3 and -ureas 5) undergo aminocarbonylation either in neat methyl orthoacetate (MOA) or in methanol containing AcONa and MOA, while exo nitrogen nucleophiles (exo-carbamates 1a,-ureas 1b, and -sulfonamides 1c) in methanol (cat. PdCl 2 , stoichiometric CuCl 2 under 1 atm of CO). The generality is indicated by the chemoselective transformations of 7a-d either into 8a-d in MOA or into 9a-d in methanol.