Radical chemistry and host-guest chemistry have each developed rapidly over the past decades and their intersection offers an attractive opportunity for modern applications. Radicals can be introduced into the frameworks of supramolecular hosts or radicals can be guests, generated in and confined to host containers. In this highlight we outline research achievements in both approaches, photoinduced and external reagent-initiated radicals in the host. Specific topics include rearrangement and fragmentation reactions, hydrocarbon oxidation and alkyl halide reductions of molecules confined to various supramolecular complexes. Applications to challenging problems in chemical synthesis are suggested.