Compassion-focused chairwork has become a recent focus of empirical investigation. This study extended this area of research by exploring how participants with depression experienced the ‘compassionate other’ imagery exercise enacted via chairwork methods. Eight individuals from primary care NHS mental health services were interviewed about their experience of the practice. The resultant data were analysed using interpretive phenomenological analysis (IPA). Three group experiential themes were identified: care that feels real, chairwork processes and encountering challenges on the road to discovery. The findings indicate that the intervention has therapeutic utility both as an intervention for cultivating compassion and as means of assessing for and identifying blocks to compassion. The results also suggest that there is potential value in enacting compassion-focused imagery techniques through chairwork methods, especially for those who have difficulty accessing mental imagery practices. The findings are contextualised within broader theory and literature, and clinical and research implications are discussed.