Abstract: A prominent principle in explaining a range of word order regularities is dependency locality, i.e. a principle that minimizes the linear distances (dependency lengths) between the head and its dependents. However, it remains unclear to what extent language users in fact observe locality when producing sentences under diverse conditions of cross-categorical harmony (such as the placement of verbal and nominal heads on the same vs different sides of their dependents), dependency direction (head-final vs head-initial) and parallel vs. hierarchical dependency structures (e.g. multiple adjectives dependent on the same head vs nested genitive dependents). Using 45 dependency-annotated corpora of diverse languages, we find that after controlling for harmony and conditioning on dependency types, dependency length minimization (DLM) is inversely correlated with the overall presence of head-final dependencies. This anti-DLM effect in sentences with more head-final dependencies is specifically associated with an accumulation of dependents in parallel structures and with disharmonic orders in hierarchical structures. We propose a detailed interpretation of these results and tentatively suggest a role for a probabilistic principle that favors embedding head-initial (e.g. VO) structures inside equally head-initial and thereby length-minimizing structures (e.g. relative clauses after the head noun) while head-final (OV) structures have a less pronounced preference for harmony and DLM. This is in line with earlier findings in research on the Greenbergian word order universals and with a probabilistic version of what has been suggested as the Final-Over-Final Condition more recently.