This chapter refers to long-term observations and research carried out in different touristic environments in the French Alps over the past 30 years. Focusing on the dilemmas and challenges of tourism policy and engineering facing climate and cultural change, it examines and discusses the processes and conditions in which the sustainable winter sports transition operates and does not operate. Indeed, on the territorial and professional levels, both very creative dynamics and a logic of inertia and (mis)adaptations can be observed at the price of strong functional contradictions and strategic tensions. This chapter attempts to show that the challenge of this tension between creativity and inertia is the exploration and affirmation of new development models that are better suited to changing local and global contexts.