Electrifying the heavy-duty vehicle (HDV) segment involves more than just substituting the technological solution; it also requires rethinking operational practices and developing digital solutions that support seamless logistics. This study investigates user needs and explores alternative concepts for booking systems for charging of electric HDVs. Based on a literature review, an analysis of relevant standards and protocols, and interviews with key stakeholders including logistics managers, planners, drivers, technology providers, and public authorities, this study identifies the key requirements for developing interoperable and user-centric booking systems for HDV charging. Insights suggest placing emphasis on avoiding digital fragmentation through the adoption of open standards, roaming, real-time data sharing, and integration with fleet and energy management systems. To illustrate potential paths forward, the study outlines three conceptual models for booking systems aiming to facilitate an accelerated and scalable charging infrastructure roll-out for HDVs in Europe and beyond.