Future development and renewal of transport infrastructures have to take into account how the effects of climate change will affect these complex sociotechnical systems. This article aims at understanding how to raise this issue to ensure an efficient and systemic uptake of climate change by infrastructure managers. It reports the results of an in-depth case study conducted on the French railway company. This study identifies several adaptation dynamics: one is top-down and stems from climate change impacts; others are more bottom-up and focused on vulnerabilities. However, both types of approaches have, so far, yielded limited results. Building on the existing literature, this paper reveals critical bottlenecks to overcome in order to get the organization ready to adapt. It suggests key components of an enabling framework for a more proactive preparation to climate change and mainstreaming climate adaptation into major organizational decisions.