We investigated the processing of ambiguous double-PP constructions in Hebrew. Selection restrictions forced the first prepositional phrase (PP1) to attach low, but PP2 could attach maximally high to VP or maximally low to the NP inside PP1. A length contrast in PP2 was also examined. This construction affords more potential locations for prosodic boundaries, and has a sharper structural contrast between the two attachment sites, than the single-PP construction which has yielded mixed results in previous work. A combined production-comprehension task showed more productions of pre-PP2 prosodic boundaries for long-PP2 than short-PP2. In comprehension, high PP2-attachment was favored by a prosodic boundary before PP2, regardless of PP2 length. This study provides performance data supporting the interplay of phrase lengths with structure-sensitivity as posited in the linguistics literature on the syntax-prosody interface, and supports the claim that readers are sensitive to the structural implications of the prosody they project onto sentences.