2020 marks the 25th anniversary of the “digital divide.” Although a quarter century has passed, legacy digital inequalities continue, and emergent digital inequalities are proliferating. Many of the initial schisms identified in 1995 are still relevant today. Twenty-five years later, foundational access inequalities continue to separate the digital haves and the digital have-nots within and across countries. In addition, even ubiquitous-access populations are riven with skill inequalities and differentiated usage. Indeed, legacy digital inequalities persist vis-à-vis economic class, gender, sexuality, race and ethnicity, aging, disability, healthcare, education, rural residency, networks, and global geographies. At the same time, emergent forms of inequality now appear alongside legacy inequalities such that notions of digital inequalities must be continually expanded to become more nuanced. We capture the increasingly complex and interrelated nature of digital inequalities by introducing the concept of the “digital inequality stack.” The concept of the digital inequality stack encompasses access to connectivity networks, devices, and software, as well as collective access to network infrastructure. Other layers of the digital inequality stack include differentiated use and consumption, literacies and skills, production and programming, etc. When inequality exists at foundational layers of the digital inequality stack, this often translates into inequalities at higher levels. As we show across these many thematic foci, layers in the digital inequality stack may move in tandem with one another such that all layers of the digital inequality stack reinforce disadvantage.