As more and more societies are transforming into cashless economies, questions about the social nature of this transformation are arising. With this paper we present specific insights into the process of the institutionalization of cashlessness in Poland. The process is analyzed from the perspective of Small and Medium Enterprises (SMEs). We advance the idea that the institutional field of cashlessness is emerging with similar pressures. In this field—as we argue using the concept of Powell and DiMaggio—SMEs experience a coercive institutional isomorphism. We show that the complex impact of interlocked social interactions, financial sanctions, narrations, values and norms are creating the matrix for SMEs’ decision whether to implement cashless payments into their business. The analysis is based on 74 individual in-depth interviews with SMEs owners. The paper is grounded in qualitative research design and the theory of neo-institutionalism.