Hypertextuality is a term that we have come to associate with digital connectivity, hypertext and the computer revolution. It is also a term that has, in retrospect, be applied to James Joyce's Ulysses. Indeed, David Gold, in a detailed case study of the text, suggests that Ulysses is 'the perfect hypertext subject.'1 Such a view assumes some kind of correspondence between Ulysses and the emergent electronic architecture of hypertext, an acknowledgment that Ulysses is somehow like hypertext. On the basis of this homology, Ulysses is seen to be eminently eligible for hypertextualisation. However, the relationship between a literary work such as Ulysses and electronic hypertext is a problematic one. While the nomenclature of hypertext and hypertextuality dates back to the late 1960s, it was for many years unknown to literary criticism. Nevertheless, its association with literature as a form of poetics can be traced back to those formative years of hypertext research and development. Ted Nelson, author of Literary Machines and originator of the term hypertext, had clearly defined it in 1965 as a literary phenomenon. The importance for Ulysses scholarship of thinking of the literary in machinic terms, and the broader logic of hypertextual poetics, will hopefully become apparent in this paper.