In communicative interactions, speakers and writers select the sentence structure most appropriate to the context from among an array of structures with similar meanings. This study investigates information structuring, focusing on how sentence constituents are organized and reordered to produce coherent and cohesive discourse. Building on previous research (Aarts, 2011, 2018; Cowan, 2013; Wasow, 1997), the study examines why and when certain structures are preferred by identifying three distinctive features—[±new information], [±complex information], and [±close linking]—and analyzing how these features interact with three information structuring principles: end-focus principle, end-weight principle, and close-linking principle. The analysis reveals that a [+new] NP tends to converge to a sentence-final position, a [+complex] NP also tends to converge to a sentence-final position, and a [+close] anaphor with its antecedent tends to converge to a coherent discourse. These findings demonstrate the systematic interaction between constituent properties and structural preferences in discourse. Pedagogical implications are discussed, including the design of consciousness-raising tasks (Ellis, 1991, 2003; Schmidt, 1990; Sharwood Smith, 1993) to help learners internalize native-like linguistic intuitions and develop a more nuanced understanding of how and why particular sentence structures are selected for a given context. The study provides insights for grammar teaching that emphasize tendencies in structural choices rather than rigid grammaticality, fostering learners’ awareness of discourse-sensitive sentence construction.