This research explores how agency is shaped not only in the use of designed objects but in their making. Through four iterations of building a digital Jacquard loom, the project shows how negotiations, failures, and adjustments actively configure agency during the design process. The loom was intentionally designed to interrupt and resist predictable behaviour, fostering a dialogical relationship between weaver and machine rather than simple instruction-following. Using a first-person perspective—documented through photographs, reflective notes, interviews, and weaving sessions—the study reveals that agency becomes most visible in moments of breakdown, offering insights for designers on how to recognise and work with agency in practice.