The repetitive size change of the electrode over cycles, termed as mechanical breathing, is a crucial issue limiting the quality and lifetime of organic electrochromic devices. The mechanical deformation originates from the electron transport and ion intercalation in the redox active material. The dynamics of the state of charge induces drastic changes of the microstructure and properties of the host, and ultimately leads to structural disintegration at the interfaces. We quantify the breathing strain and the evolution of the mechanical properties of poly(3,4-propylenedioxythiophene) thin films in-situ using customized environmental nanoindentation. Upon oxidation, the film expands nearly 30% in volume, and the elastic modulus and hardness decrease by a factor of two. We perform theoretical modeling to understand thin film delamination from an indium tin oxide (ITO) current collector under cyclic load. We show that toughening the interface with roughened or silica-nanoparticle coated ITO surface significantly improves the cyclic performance.