In this thesis, I examine the relation between the account of mechanical memory in Hegel’s Encyclopedia of the Philosophical Sciences and the speculative sentence in his Phenomenology of Spirit. Both accounts involve a transition to speculative thinking, a kind of thinking that is free from given images and representations. By discussing them together I hope to illuminate how speculative thinking functions for Hegel and why it is important. Specifically, I try to show how what Hegel calls mechanical memory can shed light on Hegel’s more familiar notion of the speculative sentence. I also draw out implications of language and mechanical memory for what Hegel calls speculative thinking.