Constructive design research is a form of research where design activity is a central research activity. One type of constructive design research is critical design, which seeks to disrupt or transgress social and cultural norms. Critical design's advocates have turned to critical theory as an intellectual resource to support their approach. Interestingly, critical design processes remain under-articulated in the growing design research literature. In this paper, we first explain why critical design is so hard to describe as a design practice or process. We then describe two critical design case studies we undertook and the effects we observed them having when place in the field. After sharing our breakdowns and breakthroughs along the way, we offer reflections on designing for provocativeness, the value of deep relationships between researchers and research participants, and the need to plan for and go with a fluid and emergent research plan - - with the goal of helping clarify critical design as an approach.