In this paper we use detailed phonetic and phonological analysis to explore the speech production of a seven-year-old child with a persisting speech disorder, across a range of speech contexts and activities: single-word naming, sentence repetition and spontaneous conversation. The analyses reveal significant differences across the different contexts, which can be related to phonetic and phonological organisation across domains larger than the single word, and in particular to specific difficulties with word juncture. The data strongly suggest that for some children a phonological analysis of single word production is unlikely to identify key characteristics of their speech output difficulties, and that due acknowledgement in the assessment of developmental speech disorders must be given not only to the tasks and contexts within which data collection takes place, but also to the nature of phonetic and phonological organisation within the context of interaction.