The combination of mechanochemistry and hypervalent iodine chemistry has rarely been reported, despite the numerous advantages offered by this enabling technology. With this in mind, this study addresses the key issue of transforming hypervalent iodine-mediated, solution-based reactions into the mechanochemical realm, accompanied by benchmarking and sustainability studies of the different types of reactions. Interestingly, several reagents displayed quite different reactivity and regioselectivity under mechanochemical conditions.