As decades turn to centuries to millennia, the contemporary relationship with the past is increasingly medieval. This article takes the perspective of extreme long-term thinking to reexamine how medieval studies can interact with more contemporary fields. How might scholars share the “now” with each other and with their predecessors from other millennia? And how might this perspective transform racial epistemologies? Inspired by the millennial thinker, Henry of Huntingdon (d. 1157), the article connects the Long Now Foundation, the 10,000-Year Clock, the poet T. S. Eliot, and the near future called the “digital Dark Ages.” Henry from the twelfth century provides a recent antecedent for imagining the “long now” wrought by settler colonialism. Undoing periodization directly challenges the colonizing deployment of time itself.