Cethrenes represent a promising platform for realizing all-organic magnetic photoswitches─provided that three requirements are met. The open form needs a thermally accessible triplet state to unlock magnetic properties, its energy relative to the closed form should lie within an accessible range, and the energy barrier between the two forms must be sufficiently high to achieve bistability. However, fulfilling the first and second criteria appear to compromise the third. Can this Catch-22 be solved? [Oxford English Dictionary defines a Catch-22 as a difficult situation or problem which cannot be resolved because the conditions necessary for its resolution are paradoxical or conflicting, with allusion to Joseph Heller's 1961 novel of the same name.].