By integrating renewables in the era of digitalization, power infrastructure is becoming more connected to ensure a secure, efficient, and decarbonized future system. However, this increased connectivity also makes infrastructure more vulnerable. Over the past decade, geopolitical tensions and concerns about energy security have influenced power systems, prompting energy professionals to explore various solutions for maintaining a reliable and resilient future. Researchers and experts from the International Smart Grid Network (ISGAN), International Council on Large Electric Systems (CIGRE), as well as system operators and communities, are exploring various solutions that focus on flexibility options, resilience, and how these two aspects can support each other. In particular, they continue to work on energy system stakeholders’ interaction to identify a key pathway to a clean, reliable, and secure energy future. In ISGAN, the experience from flexibility definition and characterization started in 2019, and continued with flexibility for resilience in integrated systems activity supported by the International Energy Agency in 2022; recent outcomes from an ISGAN workshop held in 2023 on the topic of “Flexibility for Resilience and Power System Stakeholder Interaction” are summarized and discussed here. This article presents the results and best practices derived from collaboration and the exchange of experiences between countries. It highlights the potential, role, and actions being taken by various stakeholders, including academia, society, policymakers, regulators, urban planners, system operators, retailers, and consumers, in addressing the urgent need for power system resilience and the critical role of flexibility.