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Explore the challenges and strategies of building proactive recommendation systems for complex software platforms in this DevConf.CZ 2023 conference talk. Delve into the world of observability and automation as Jan Holeček discusses the importance of proactive problem-solving in service and app provision. Compare the ease of implementing recommendations for public cloud providers versus the complexities faced by platforms like Red Hat OpenShift with diverse deployment options. Gain insights into the technical hurdles encountered when developing a knowledge base for proactive recommendations, using Red Hat Insights for OpenShift as a case study. Learn about the intricacies of delivering quality service, avoiding disruptions, and enhancing customer satisfaction through intelligent, preemptive problem-solving mechanisms.