The present corpus-based study deals with eight sets of rivalling prepositions in verb-dependent prepositional phrases. The two or three members of these sets, though equivalent in specific uses, differ in terms of functional explicitness. For instance, in directional uses, into can be regarded as more explicit than in. The main objective is to demonstrate for each of these sets that, in line with the Complexity Principle, the more explicit items are favoured in more complex grammatical environments. The contexts under scrutiny include those produced by passivisation, Heavy NP Shift, object relativisation, the use of full object NPs rather than personal pronouns, and preposition stranding. Thus, we observe that – compared with basic active clauses – preposition stranding in the active induces increased shares of the more explicit prepositions in question. Predictably, even higher degrees of prepositional explicitness are found with the combination of preposition stranding and passivisation. Also, it is shown that Heavy NP Shift tends to trigger greater proportions of the more explicit prepositions than object relativisation. The observed tendencies hold for Present-day English and earlier stages of English as well as for morphologically related and unrelated rival prepositions.