Objective Gratitude has consistently been associated with various beneficial health-related outcomes, including subjective wellbeing, positive mental health, and positive physical health. In light of such effects, positive psychology researchers and practitioners have often implemented gratitude interventions in an attempt to build individuals’ orientations toward appreciation and thankfulness. Recent meta-analyses and reviews have revealed, however, that these interventions often have mixed effects on gratitude or other health outcomes. With this issue in mind, we aimed to identify (a) contextual considerations that may impact the effectiveness of these approaches, and (b) recommendations for the optimisation of gratitude interventions. Methods and Measures Seventeen mental health professionals or experienced health psychology researchers engaged in semi-structured interviews to address the research questions. Results Thematic analysis of the data resulted in three contextual themes—cultural considerations, personal characteristics, and life experience—that were discussed as factors likely to influence intervention effectiveness. With respect to recommendations, participants highlighted the importance of encouraging deep engagement in gratitude tasks, consistent repetition of those tasks, and the value of interpersonal expressions of gratitude. Conclusion Discussion is centred on suggestions for future research on gratitude and on implications for the implementation of gratitude interventions.