Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy‐to‐access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation. Sulfonamides are prevalent in drug molecules, however, methods for functionalizing sulfonamides via S−N bond cleavage are scarce. Based on a re‐evaluation of N−Ts deprotection, we developed sulfonyl pyrroles as linchpins for sulfonamide functionalization. Sulfonyl pyrroles engage in various transformations that can proceed through chemical, electrochemical or photochemical pathways.