This article investigates the role of stakeholder engagement in the development and deployment of GovTech solutions, using WiseTown—an Italian City Digital Twin (CDT) ecosystem of digital solutions—as a case study. Rooted in a socio-technical perspective, the study explores how engagement with diverse stakeholders—municipal leaders and technical officers—shapes the co-design, adaptation, and scaling of GovTech solutions in real-world contexts. Drawing on a semi-structured expert interview and supported by secondary materials, the analysis explores how WiseTown’s digital ecosystem evolves through collaborative practices. The findings are structured around four key facets of stakeholder engagement: entry points and layered engagement strategies; co-design and feedback mechanisms; handling institutional resistance; and inter-municipal scaling. The study highlights a set of mechanisms—such as co-design workshops, civic tech modules, and flexible deployment models—that foster both top-down and bottom-up stakeholder engagement. These approaches enable the co-evolution of digital tools with the needs of local administrations and communities. Lessons derived from the case underscore that stakeholder engagement is not just a participatory ideal but a practical enabler for adoption, usability, and scalability. The article contributes to the GovTech literature by offering empirical and actionable insights on how engagement can overcome institutional resistance, support collaboration, and ensure long-term relevance, while enabling the design and institutionalization of inclusive, scalable, and context-sensitive public sector innovation.