Since the introduction of agile methods in the 1990s, practitioners and researchers have shaped and adapted agile practices to meet the demands of rapidly changing markets. Today, agile methods are applied globally across industries, company sizes, and cultural contexts, and are increasingly challenged by disruptive forces such as remote work and AI integration. Despite this success, a clear gap between research and practice remains. Our first Agile PR Workshop at XP2025 identified three critical dimensions of this gap: the time-gap, where research lags behind the speed of practice, and the theory-gap, where research often lacks generalizable frameworks to strengthen empirical insights. Also, we identified a transfer-gap, where valuable insights and findings fail to reach practitioners in an accessible, applicable, and sustainable form. The second iteration of the workshop continues this exploration, offering a platform for researchers and practitioners to engage in structured discussions, share empirical findings, and reflect on industry experiences. The goal is to collaboratively develop a research roadmap that bridges the theory–practice divide, while inspiring new collaborations and joint projects. Participants will contribute to shaping future research directions, ensuring that academic work provides timely, actionable, and theoretically grounded insights for agile practice. Ultimately, this workshop aims to strengthen the community of researchers and practitioners dedicated to advancing agile software development together.