We present an interdisciplinary study on the interaction between the interpretation of noun-noun deverbal compounds (DCs; e.g., task assignment) and the morphosyntactic properties of their deverbal heads in English. Underlying hypotheses from theoretical linguistics are tested with tools and resources from computational linguistics. We start with Grimshaw’s (1990) insight that deverbal nouns are ambiguous between argument-supporting nominal (ASN) readings, which inherit verbal arguments (e.g., the assignment of the tasks), and the less verbal and more lexicalized Result Nominal and Simple Event readings (e.g., a two-page assignment). Following Grimshaw, our hypothesis is that the former will realize object arguments in DCs, while the latter will receive a wider range of interpretations like root compounds headed by non-derived nouns (e.g., chocolate box). Evidence from a large corpus assisted by machine learning techniques confirms this hypothesis, by showing that, besides other features, the realization of internal arguments by deverbal heads outside compounds (i.e., the most distinctive ASN-property in Grimshaw 1990) is a good predictor for an object interpretation of non-heads in DCs.