There is a global urgency for digital transformation in public institutions, and Romania, particularly at its local levels, is actively participating in this trend. Cluj-Napoca, Romania’s second-largest city, emerges as a pioneer in digitizing local public services, catalysed further by the 2020 pandemic, and by a new digital strategy. This case study looks at the city’s journey, employing expert interviews, observation, and data analysis, to assess the efficacy of internal organizational changes aimed at enhancing digital public services. Notably, our findings reveal a somewhat paradoxical scenario: while the technical hurdles of digitalization are more straightforward to navigate, challenges rooted in altering established processes, mind-sets, as well as traditional resistance to change prove more daunting. Moreover, the case of Cluj-Napoca underscores the critical role of community support, where external resources like knowledge, expertise, and advocacy can compensate for internal deficits. Effective coordination of these diverse resources is pivotal, often dictating the trajectory of digital transformation initiatives. This study not only sheds light on the complexities of digitalizing public services but also offers insights into managing change in public institutions.