This white paper showcases effective monitoring and optimization of a photochemical transformation via a Syrris Asia Flow Chemistry System and an in-line Bruker Fourier 80 benchtop nuclear magnetic resonance (NMR) spectrometer. The combination of instrumentation is a powerful framework that enhances and streamlines reaction optimization to improve product yield, which is demonstrated with the flow photooxygenation of 1,5-dihydroxynaphthalene to obtain Juglone. The precise control over reaction parameters from the flow chemistry system used and the real-time monitoring of the reaction from in-line NMR analysis led to more reliable and efficient fine-tuning of reaction parameters and output. The results from this reaction optimization demonstrate the value of integrating benchtop NMR into process chemistry development for improved process control and optimization.