This article will be drawing on two cases to reflect on the impact of different ways of practicing civic engagement in urban digitalization policy. Both cases reflect on the importance of cities playing an active role in the promotion of digital rights, obligation of public participation in digital policy making, and need for political digital education to enable democratic conversations on digital transformation. From a democratic theory point of view, the shifts happening through the digitalization of societies raise interesting questions regarding what modes of governance should be implemented for improving digital sovereignty, which could be in line with “locally” grounded politics. Theoretically, the article will frame these issues of governance and civic participation within the literature on “digital sovereignty,” understood as going beyond national territory toward issues of independence, democratic control, and autonomy over digital infrastructures, technologies, and content.