To account for several asymmetries between A- and Ā-movement, Takahashi and Hulsey (2009) generalize the late merger option ( Lebeaux 1988 , Chomsky 1995 ) as wholesale late merger (WLM). In particular, allowing an NP to merge with a head D as late as (but no later than) its Case position explains why Ā but not A-movement displays Principle C reconstruction effects. In this article, I claim that WLM is also responsible for pervasive asymmetries within the class of Ā-extractions. The evidence comes from restrictions on English preposition stranding. I document a correlation between a preposition’s complementation properties and its ability to be stranded: prepositions that disallow pronominal complements can only be stranded by a subset of Ā-extractions. I argue that the extractions allowing pronoun-rejecting prepositions to be stranded disallow WLM, while those that disallow the stranding allow (and require) WLM.