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This open access book constitutes the research workshops, doctoral symposium and panel summaries presented at the 20th International Conference on Agile Software Development, XP 2019, held in Montreal, QC, Canada, in May 2019. XP is the premier agile software development conference combining research and practice. It is a hybrid forum where agile researchers, academics, practitioners, thought leaders, coaches, and trainers get together to present and discuss their most recent innovations, research results, experiences, concerns, challenges, and trends. Following this history, for both researchers and seasoned practitioners XP 2019 provided an informal environment to network, share, and discover trends in Agile for the next 20 years. Research papers and talks submissions were invited for the three XP 2019 research workshops, namely, agile transformation, autonomous teams, and large scale agile. This book includes 15 related papers. In addition, a summary for each of the four panels at XP 2019 is included. The panels were on security and privacy; the impact of the agile manifesto on culture, education, and software practices; business agility – agile’s next frontier; and Agile – the next 20 years.