The euphemism "female trouble" (discreetly referring to women's health experiences) suggests that trouble is linked to women and bodily transitions women can go through. However, trouble is not only a noun; it is also a verb with a strong feminist tradition. In this article, I present troubling design; a theoretically grounded and practice-oriented design program for designing with women's health. Troubling design brings to matter how trouble is an implicit condition of designing ethical and responsible technologies for women's health. By designing with trouble, troubling design encourages designers and researchers to develop knowledge embedded in criticality and questioning status quo, in order to expand their perspectives on designing with intimate and tabooed bodily experiences. Grounded in feminist theory and research-through-design, troubling design contributes with analytical and generative design knowledge articulated through design examples and three practices: staying with the wrong, curious visiting, and collective imagining. CCS Concepts: • Human-centered computing → Interaction design;