Controlled sulfonyl migration is considered an important transformation for total synthesis, and scaffold elaboration. Accordingly, efforts to understand the underlying properties of these often serendipitously identified reactions have important implications. Following the attempted synthesis of a tetrahydroindazolone analogue, we report here an unexpected 1,5 nitrogen to carbon tosyl migration, resulting in the isolation of an unusual sulfonated dimedone. Synthetic and mechanistic investigations provide early insight into the scope of this reaction, with two potential mechanisms proposed.