Real-time NMR spectroscopy has proven to be a rapid and an effective monitoring tool to study the hypervalent iodine(III) mediated cyclopropanation. With the ever increasing number of new synthetic methods for carbon−carbon bond formation, the NMR in situ monitoring of reactions is becoming a highly desirable enabling method. In this study, we have demonstrated the versatility of benchtop NMR using inline and online real-time monitoring methods to access mutually complementary information for process understanding, and we developed new approaches for real-time monitoring addressing challenges associated with better integration into continuous processes.University of Cambridge (Daphne Jackson Fellowship), iCON through CMAC (Grant ID: RG74817), Engineering and Physical Sciences Research Council (Critical Mass grant (Grant ID: EP/K009494K/1), Core Capability grant (Grant ID: EP/K039520/1