In Old English, /-n/ loss started in early Northumbrian and spread to the southern dialects after about 1050. An important diagnostic of the transition to Middle English, the loss is commonly assumed to be morphologically driven. However, /-n/ loss in atonic syllables could also be phonologically-conditioned: aweġ ‘away’<onweġ, abūtan ‘about’<onbūtan. In Middle English, the loss proceeded rapidly, but the triggers behind the different rates of change and the different results for the various categories have not been fully explored. Using LAEME, we survey all attestations of /-n/ loss, enriching the empirical data-base on the change. The findings show significant differences within word-classes, and differences between inflectional and derivational suffixes. This raises a set of theoretical questions: why did only /-n/ inflections lose their codas, why was the productivity of verbal derivational /-n/ phonotactically restricted, what justifies the loss or retention of /-n/ in stems? We look into the interplay of phonological and morphological factors, isolate the sets in which the results appear to be phonotactically driven, and address the phonotactic dimension in relation to other factors, both within and above the word level. In noun plurals, /-n/ loss emerges as the clearest case of avoidance of phonotactically suboptimal sequences at the word level. A statistical comparison of the end-points of the change reveals that overall frequency has stayed constant and has no obvious direct bearing on the process, while the presence of /-n/ as a morphological marker has changed significantly. The paper ends by identifying aspects of the history of /-n/ that remain uncharted.