Here we explore the incorporation of photoresponsive diazene precursors as one of the components of a covalent organic cage. Organic cages incorporating azobenzene functionality were first designed based on synthetically accessible precursors and investigated using computational methods, prior to investigation of synthetically viable cage structures in an experimental screen. Two azobenzenecovalent cages (ACC) were discovered; a novel Tet 3 Di 6 tubular cage (ACC-1) consisting of three tetratopic (Tet 3 ) aldehydes and six ditopic (Di 6 ) amines, and a Tri 2 Di 3 capsule (ACC-2) consisting of two tritopic (Tri 2 ) amines and three ditopic (Di 3 ) aldehydes, and their photoswitching behaviour investigated through a series of UV-Vis and 1 H NMR spectroscopic studies. Each cage is capable of three-fold isomerization, using either ditopic or tetratopic aldehydes containing diazene functionality. The photoswitching behaviour of the two azobenzene moieties on incorporation into the cage structures was also investigated by comparing them to single azobenzene-imine subunits. Finally, with the Tet 3 Di 6 cage exhibiting superior photoswitching properties compared to the Tri 2 Di 3 cage, a detailed kinetic analysis of the thermal isomerization for each of its EEZ, EZZ and ZZZ metastable isomers was conducted.