This paper focuses on digital agency in fashion and textiles design, presenting a case study using a digital drawing tool to gain insights into the experiences of creative agency and interactions with an automated computer agent. This study is positioned within the wider Neo Couture research project, which aims to develop a digital hand embroidery learning tool for fashion and textile practitioners. The paper draws upon a developing project framework, grounded in principles informed by haute couture as a lens to articulate the data analysis and findings. Centring on the framework’s aspects of Material Agency and Interactions, in particular the agency of the tool, this study finds a nuanced interplay between human practitioners and the tool developed for this study. Further quantitative insights are drawn from the workshop tool itself to give a richer understanding of both user experience and creative interactions synchronously. Theory in digital craftsmanship is discussed in relation to this study, highlighting the need to account for the ways that fashion and textiles practitioners relate to materials in their work when developing supportive digital applications in this space. This research supports future work to be undertaken with more diverse cohorts of practitioners in fashion, textiles, and haute couture practice. The findings are particularly relevant for interdisciplinary fashion and textile practice in conjunction with HCI and digital design, towards the development of pedagogical AI tools for craft learning in fashion and textiles.