I take information structure as a component of the sentence grammar that was proposed by Lambrecht (1994) as a starting point. In this view, information structure is understood to be a decisive factor in the formal structuring of a sentence. I am presenting the results of research, which shows that word order (WO), or the order of sentence components on the syntactic, as well as on the phonological level, is conditioned by the propositional structure of the sentence. Such a system results in an extremely low number of restrictive rules that, from the point of view of WO, define ungrammatical sentences. This research is a methodological attempt to combine insights from formal and functional approaches to grammatical analysis based on Croatian examples. The Croatian language is traditionally held to be a language in which the order of syntactic components is (relatively) free, while the position of clitics and clitic clusters is considered (relatively) restricted. I show that clitics and clitic clusters are not anomalous in such a system, but rather a form of dynamization of the sentence content that native speakers accept as an open possibility. Previous research on WO in Croatian has failed to recognize these relationships because of two major obstacles. The first one concerns the fact that this research was concerned solely with so-called ‘neutral’, contextually unconditioned sentence types that is, only those that are at the null level of informativeness and answer the question ‘What is going on?’. The second obstacle concerns the lack of empirical research, both corpus-based and psycholinguistic, which opens an entirely new insight into the linguistic structure and fine-grained possibilities of its expressiveness at the level of information structure.