Context Dignity therapy (DT) is a psychotherapeutic intervention whose aim was to bolster the sense of purpose, meaning, and sense of dignity in patients with terminal disease. Objectives The aim of this study was to explore, compare, and better understand the content of standard DT, waitlist DT (WDT), and Life Review (LR) that used the DT interview protocol but omitted the creation of legacy documents. Methods Efficacy of these interventions was previously documented in a sample of 56 participants. In this study, DT and WDT legacy documents and LR session transcripts were qualitatively analyzed using the Framework approach, both deductively and inductively. Results All participants expressed a diverse set of beliefs, values, memories, and important relationships with the majority also indicating at least some sense of meaning and acceptance despite disappointments, regrets, and the impacts of illness. Sense of legacy, fighting spirit, and hope were particularly prevalent in legacy documents (DT and WDT groups), whereas relationship regrets, self-blame, unfinished business, and aftermath concerns were more likely to be expressed during the LR process. Themes of spirituality, illness impacts, and unfinished business were relatively less common in WDT participants. Conclusion This study provides further insight into what palliative care patients consider to be most important and meaningful to them when taking part in DT and LR. Creating legacy documents is likely to result in session content that is different in several key areas compared with LR, even when controlling for interview questions, therapist influences, and session length. Consideration of the above is essential in optimizing psychotherapeutic outcomes near end of life.