Electrophilic aromatic substitution (S[subscript E]Ar) and nucleophilic aromatic substitution (S[subscript N]Ar) reactions are among the most valuable reactions in the conversion of aromatic rings. While these reactions are typically covered in separate experiments in undergraduate organic courses, a continuous experimental setup elucidating both S[subscript E]Ar and S[subscript N]Ar processes remains unexplored in the literature for undergraduate laboratories. We herein described a two-step experimental design to cascade the S[subscript E]Ar and S[subscript N]Ar reactions, aiding students in better understanding the similarities and differences of these conversions as well as introducing the concept of umpolung. The experiment also reinforces students' proficiency in fundamental organic synthesis techniques and workup procedures, such as TLC analysis, chromatography purification, recrystallization, and handling LRMS and NMR.