In typical speech words are grouped into prosodic constituents. This study investigates how such grouping interacts with segmental sequencing patterns in the production of repetitive word sequences. We experimentally manipulated grouping behavior using a rhythmic repetition task to elicit speech for perceptual and acoustic analysis to test the hypothesis that prosodic structure and patterns of segmental alternation can interact in the production planning process. Talkers produced alternating sequences of two words (top cop) and non-alternating controls (top top and cop cop), organized into six-word sequences. These sequences were further organized into prosodic groupings of three two-word pairs or two three-word triples by means of visual cues and audible metronome clicks. Results for six speakers showed more speech errors in triples, that is, when pairwise word alternation was mismatched with prosodic subgrouping in triples. This result suggests that the planning process for the segmental units of an utterance interacts with the planning process for the prosodic grouping of its words. It also highlights the importance of extending commonly used experimental speech elicitation methods to include more complex prosodic patterns, in order to evoke the kinds of interaction between prosodic structure and planning that occur in the production of lexical forms in continuous communicative speech.