The metaphysics of individuation, like the historical and contemporary senses of ‘individuate’ and its cognates, is a complex web of difficult issues. The spin Leibniz gives to them can be properly traced out only against the scholastic backdrop that was his intellectual heritage. In this chapter we undertake a brief journey through the conceptual network in the vicinity of “individuation” –first as a means of distinguishing related questions that can be asked about our topic (§1), and then as a means of highlighting similarities and differences between contemporary and scholastic ways of understanding them (§2). With these introductory remarks in place, it will then be possible (§3) to make vivid the central threads (as we see them) in the early Leibniz's (1663) Disputatio Metaphysica de Principio Individui, anticipating finally two important themes in the mature Leibniz (§4). Here – and indeed in the remaining chapters – we are not simply aiming to locate points of historical continuity. Much as contemporary readers are more comfortable with the mature Leibniz on substance and individuation as against the apparently contorted efforts of the scholastics to engage with roughly the same set of problems, one should not lose sight of ways that scholastic insights into problems and possible solutions were rejected and largely forgotten rather than refined and extended into the modern period. Then as now, continuity isn't everything.