Agile methodologies often do not explicitly include the process of creating user documentation, consistent with the idea that documentation should be minimal to create efficient processes. While Agile provides several advantages for technical communicators, these processes also raise challenges that technical communicators creating user documentation need to address, including collaborating with development teams and evaluating the usability of user documentation. Building on existing research, this qualitative study aimed to understand both the advantages and challenges of Agile and illuminate how technical communicators and their colleagues address the challenges. We interviewed 14 practicing technical communicators and their colleagues over 3 months in the fall of 2022. Participants worked in six software development organizations across the United States, with one working in Europe. We analyzed results qualitatively to discern findings focused on three topics—general advantages and challenges of creating user documentation in Agile contexts, the dynamics of technical communicators interacting with Agile development teams, and the effects of Agile on assessing the usability of user documentation. We offer suggestions for practitioners and educators as they consider how Agile affects the creation of user documentation, leveraging the benefits of Agile, and addressing challenges in innovative ways as demonstrated by participants in this study. Future research will provide even richer perspectives.