Vapor condensation is a crucial phenomenon governing the efficiency of many processes. In particular, dropwise condensation on hydrophobic thin films (≈100 nm-thick) has the potential to achieve remarkable heat transfer. However, the lack of durability of these thin films has limited applications for a century. Although degradation due to steam condensation has been described as "blistering," no satisfactory insight exists capable of elucidating the driving force for film delamination. Here, it is shown that nanoscale pinholes in hydrophobic films are the source of blister formation. By creating artificial pinholes via nanoindentation on thin (30 to 500 nm-thick) fluorinated hydrophobic films, it is demostrated that water blisters can be initiated at the pinholes during condensation. It is experimentally demonstrated that vapor is transferred to the blister through the nanoscale pinhole, and the driving force for delamination is capillary pressure generated at the pinhole by the pinned liquid-vapor interface. The techniques and insights presented here will inform future work on polymeric thin film and enable their durable design for a variety of applications.