Cautionary tales have been an essential part of a design imagination that has attempted to frame the relationship between the systemic complexity of design problems and what counts as modern architectural solutions in other ways. Cautionary tales do not seek consensus, leading to proposing design resolutions or establishing a given technical fix as a norm. Instead, they make productive use of differences manifesting as contradictions, ambiguities, and paradoxes and provoke the need to reframe the problem itself. In published formats, cautionary tales appear early on in the context of children’s literature.