Counterfeiting is a pervasive problem, especially in countries like Italy, which boasts one of the most famous national brands in the world: “Made in Italy.” This illegal activity not only jeopardizes the brand’s reputation but also undermines the business results of companies, including small and medium-sized enterprises (SMEs). Although new digital technologies such as blockchain and the Internet of Things (IoT) offer opportunities in the fight against counterfeiting, their use is not widespread, especially in Italian SMEs. Our study investigates the barriers to the adoption of anti-counterfeiting technologies in Italian SMEs through an exploratory analysis. The preliminary results show the importance of traceability and trust within supply chains and shed light on the many challenges companies face when adopting anti-counterfeiting technologies. This study gives managers valuable insights into the complexities of deploying anti-counterfeiting technologies to protect brand integrity and business sustainability.