Synthesis of (Z)-alkenes is challenging because the (E) stereoisomers are usually more stable. Energy transfer photocatalysis has emerged as an efficient strategy for (E) [right arrow] (Z) alkene isomerization. We report the development of an advanced undergraduate laboratory experiment that introduces students to contemporary organic photocatalysis methods and theory within the context of the energy transfer photocatalyzed (E) [right arrow] (Z) isomerization of 2-nitrocinnamaldehyde. Students assess the ability of the photocatalysts [Ru(bpy)[subscript 3]][PF[subscript 6]][subscript 2] and [TPP][BF[subscript 4]] to promote substrate isomerization, monitor and analyze reactions by [superscript 1]H NMR spectroscopy, and probe the isomerization mechanism via computational chemistry. This work uses the Wisconsin Photoreactor Platform, a source of affordable, readily fabricated, and reliable photoreactors.