This paper addresses the syntactic and rhythmic conditions on prosodic restructuring in iGeneration Taiwanese. The iGeneration, who grew up with an iPhone, or a smartphone, in hand, is loosely referred to people born between 1995 and 2005. The speakers of iGeneration Taiwanese tend to parse them into short fragments, which correspond to smaller phonological phrases. The categorical distinction between lexical and functional projections plays a role in phonological phrasing. Rhythmic restrictions then serve to avoid an oversized phonological phrase. In this paper, I posit a series of alignment and rhythm constraints, and offer an analysis through constraint interaction.