Urban freight transport faces significant environmental and societal challenges, necessitating innovative solutions. This paper explores the business model implications of such solutions, drawing insights from research trials conducted in Bremen, Mechelen, and Groningen as part of the “Urban Logistics as an on-Demand Service” (ULaaDS) project. While many proposed solutions are technologically ready, their integration into existing business practices and scaling for impact remains challenged. Key findings highlight the tension between innovative solutions and entrenched business-as-usual models. The interplay between private business and public authorities emerges as an important factor, with mutual expectations shaping the trajectory of these solutions. The research underscores the need for a holistic approach, integrating technological, business, and regulatory facets, to ensure sustainable urban freight transport solutions can compete effectively.