Nancy Dorian's foundational work on the loss of Gaelic in the East Sutherland communities continues to provide important insights into the nature of the process of language change in situations of obsolescence. In this article I look at a subset of Dorian's data from the perspective of current syntactic theory, and argue that the connected loss of such apparently different constructions as objects of non-finite verbs, inalienable possessive structures, and a range of passives, and the concomitant restructuring of the grammar, all follow from the interaction between a reduction in agreement features on a functional head and the broad syntactic ecology of the language. This approach makes sense of why these apparently disparate constructions all undergo the particular kinds of change that are seen, changes which are mysterious from the perspective that an obsolescing language should alter to become more like the dominant language (in this case English) which is replacing it.