Contemporary organizations investing in digitalization initiatives aim at enhancing their productivity, streamlining their processes, or just cutting their costs. However, little is known about the impacts of how digitalization initiatives create value, for whom, or where and when these occur. In this paper, we study what kinds of impacts different digitalization initiatives in a midsized city create and for whom. We show that they vary for different stakeholders and according to their perspectives. Potential impacts diverge for city employees, decision makers, citizens, organizational activities, and the public sector in general. Our findings show that potential impacts are multifaceted and numerous. This has implications for the assessment of the success and the benefits of digitalization initiatives or information systems investments; they vary according to the stakeholders and their expectations. The distinction between the digitalization experiment with its novelty and uncertain suitability for the purpose and the standardized service is essential.