This article explores the history of Wikipedia and Wikimedia as a unique example of the evolving concept of digital sovereignty. With roots in the open, free, and non-profit model, Wikipedia has become a global phenomenon. Based on the authors’ extensive involvement since the early years, this article examines Wikipedia’s journey of over two decades to unravel relevant aspects of sovereignty within its unconventional organizational framework. The concept of digital sovereignty was nascent when Wikipedia emerged in 2001. In its 24-year evolution, Wikimedia’s atypical organizational model, shaped by a mix of intent and happenstance, fostered digital independence while unintentionally creating pockets of dependence. Looking at the origins and the foundational principles, this article sheds light on various aspects of dependence, brought about in the areas of content, collaboration, governmental influence, legal framework and funding models. The article concludes by highlighting the cultural dimension of digital sovereignty, emphasizing how Wikipedia’s digital sovereignty is the result of foundational philosophies, open ideation spaces, and iterative adaptation.