Since the 1990s, there has been a growing interest in applying qualitative conversational analysis (CA) and discourse analysis (DA) methodologies to clinical discourse data. Research into dementia, for example, has examined the types of conversational strategies utilized by both individuals with dementia and their interlocutors (e.g. Bohling, 1991; Garcia & Joanette, 1994; Goldfein, 1990; Hamilton, 1994; Milroy & Perkins, 1992; Penn, Sonneberg & Schnaier, 1988; Ripich, Vertes, Whitehouse, Fulton & Ekelman, 1991). Drawing on frameworks suggested by Orange, Lubinski and Higginbotham (1996) and Watson, Chenery and Carter (1999), this chapter will examine discourse data taken from audiotaped conversations between one of the researchers and a 79year-old woman suffering from Alzheimer’s disease (AD) with non-specified stroke-damage, and a long-established hearing impairment. While examining the efficacy of the above frameworks, we also raise the issue of how we identify potential trouble-sources in relation to the perception of conversational satisfaction.