The recent catastrophic wildfires in Portugal and Chile shared similar features, not just because they developed under extreme weather conditions but also because extensive forest plantations were involved. Dense forest plantations of flammable pine and eucalypt species favor the development of high-intensity large fires, threatening people and the forest industry sustainability under increasingly frequent and severe drought events. Preventive land-use planning and cost-effective fuel management are key elements of sustainable forestry. Understanding the fire ecology context prior to plantation establishment is also crucial for the success of fire management planning. Although the forest industry has contributed to the economy of these countries, improved regulation and science-based management policies are strongly needed. Fuel treatment strategies can be optimized by risk-based modeling approaches, and should be mandatory in wildland-urban interfaces. The tragedy caused by these wildfires is an opportunity to change towards more sustainable landscape arrangements that reconcile ecosystem services, biodiversity conservation, and protection from life-threatening wildfires.