<p>In this paper, I explore cycle-tracking from a first-person perspective, conducting a four-month autoethnography in which I track my cycle using the apps Clue, Flo, and Natural Cycles. In doing so, I approach cycle-tracking as a Postdigital intimacy—a becoming with technology. I ask how cycle-tracking intimately shapes lived experiences and knowledge of the cycle<i>,</i> and contribute with an empirical understanding of what it means to intimately know and experience the cycle with these apps. Through a Crip Technoscience ,<i>y</i>,<i>5</i> and Crip Human–Computer Interaction perspective, I explore the intimate frustrations that emerge between me and the apps, and how the apps and I work—and fail—together. By combining this with Karen Barad's concept of intra-action, I show how app use becomes larger than the sum of its parts—the user and the technology—through the emergence of intra-actional agencies in between the app and the user. My analysis shows how app cycle-tracking intimately shapes not only the knowledge and lived experience of the cycle, but also the experience of Postdigital life itself. Cycle-knowledge becomes an explanatory framework readily applicable to all kinds of lived experiences, and intra-action with the apps becomes an intimate agency that can be blamed on neither the apps nor the user. Postdigital feminisms, I argue, need to take the intimate intra-actional agencies that appear between technologies and users seriously, and approach and design technologies not with perfection as the default setting, but with failure.</p>