The increasing dynamism and complexity of modern software-intensive systems pose significant challenges to their efficient and reliable operation and management. Particularly evident in cloud-native applications and microservice-based architectures, human operators are facing growing cognitive burdens in detecting, diagnosing, and resolving issues, as well as in optimizing performance and making decisions before, during, and after incident occurrence. Traditional monitoring and reactive strategies are no longer sufficient to address these challenges. Instead, modern system complexities and uncertainties demand a shift toward robust, automated, and autonomic capabilities that can reason about dynamic system states, anticipate disruptions, proactively adapt configurations, and propose resolutions before failures occur. This CASCON workshop explores the convergence of recent innovations in Artificial Intelligence (AI) such as the Application of AI to the Operation of Software Systems (AIOps), Generative AI (GenAI), and Digital Twins (DTs) as a foundation for building next-generation platforms for proactive continuous operations. This combination of transformative technologies promises a new operational paradigm that reduces operator burden while enhancing system dependability and resilience. Our workshop aims to bring together researchers, practitioners, and technology leaders to share research breakthroughs, industrial case studies, frameworks, and tools that enable the anticipation, diagnosis, and remediation of operational issues before they impact production environments.