The reactions of the chalcogen halides (Ch = S, Se, Te) with a series of diiminopyridine (DIMPY) ligands were explored. It was determined through these studies that varying both the substitution on the a-carbon and the chalcogen halide reagent afforded different products. If methyl groups were present on the a-carbon, reactivity was observed through the eneamine tautomer to yield N,N',C-bound neutral chalcogen complexes. In the cases where H and C6H5 groups were in the same position, N,N,N ''-chelated chalcogen cations or dications were produced. Many of the reactions resulted in complex mixtures postulated to occur by the release of halogen decomposing the product or, for reactions with the CH3 substituted ligand, uncontrollable reactivity with the eneamine tautomer. This is the first report of reactions of sulfur and selenium halides with the ubiquitous diiminopyridine ligands and only the second example for a tellurium halide.