This book presents the thoroughly refereed and revised post-workshop proceedings of the 19th Monterey Workshop, held in Beijing, China, in Ocotber 2016. The workshop explored the challenges associated with the Development, Operation and Management of Large-Scale complex IT Systems. The 18 revised full papers presented were significantly extended and improved by the insights gained from the productive and lively discussions at the workshop, and the feedback from the post-workshop peer reviews. 2016 marks the 23rd anniversary for the Monterey Workshop series which started in 1993. For nearly a quarter of century, the Monterey Workshops have established themselves as an important international forum to foster, among academia, industry, and government agencies, discussion and exchange of ideas, research results and experience in developing software intensive systems, and have significantly advanced the field. The community of theworkshop participants has grown to become an influential source of ideas and innovations and its impact on the knowledge economy has been felt worldwide.