Dissatisfied with contemporary notions of ‘transparency’ in software, rigid computational logics, and the resulting limitations for design, computational designers critically question their work through interrogative processes. Paul’s subverting and hacking Revit revealed cracks in the façade of the architectural software in which to work. Maria depicted the open mindset of younger children as preferable to one which merely solves problems. And Ken playfully and poetically illustrates how computation can serve as generative metaphors for design thinking. In interrogating, computational literacy and thinking skills become valuable not only for producing optimized, efficient solutions to problems, but for expanding spaces of possibility and arriving at new understandings. The Coons patch software reconstruction serves as an example of an interface through which seemingly opaque geometries might be interrogated by non-technical users. In teaching basic programming and computational thinking, this fact should be stressed: That computation is as much a mode of problem-solving as it is problem-framing. A solution to a complex problem arrived at through computation alone inevitably misses the bigger picture. However, approaching computation as an interrogator, empowered to critically question the story it tells, a designer working computationally can discover and operationalize new ways of seeing the world.