As technology permeates people's everyday lives, opportunities arise for HCI to design, develop and research technologies that focus on broader societal challenges such as sustainability, race, gender, and power. Toward this end, we present the Troubling Cups, a provocative design that makes trouble about unequal pay in a work environment. The design was produced through a series of workshops in which women discussed, identified and provotyped trouble in their work environments. Through a small, two-day field study, we explored if and how the provotype made trouble about unequal pay in real-world settings, and how the participants stayed with the trouble of unequal pay. We contribute to our research field with the provotype itself, our qualitative findings, and with our reflections and lessons learned on making trouble and staying with the trouble through provotyping.CCS Concepts: • Human-centered computing → Empirical studies in HCI.