Here, we present an alternative approach for pyridine halogenation via a ring-opening, halogenation, ring-closing strategy (Figure ). The one-pot protocol uses a modified version of the classic Zincke ring-opening reaction that converts pyridines into azatriene intermediates, or "Zincke imines." This synthetic maneuver temporarily transforms pyridines from electrondeficient heterocycles to a series of polarized alkenes that undergo facile reactions with Nhalosuccinimides. The halogenation process is 3-selective across a range of substituted pyridines, functions on complex structures, including pharmaceuticals, and can be immediately adopted by practitioners.