Technology for promoting reflection can help people better understand their emotions and thought patterns, eventually motivating them to take action to adopt healthy or productive behaviors. However, existing work has often viewed users individualistically, addressing people's behaviors and emotions rather than recognizing the external factors that shape them (e.g., economic status, culture). We envision that the individualistic approaches can be extended and reimagined in ways that can consider such broader contexts. We believe such a shift in the design of interventions will help individuals reflect in a more holistic manner, supporting collaborative reflection processes that involve more than one person. With these aims in mind, we will discuss the two questions in our workshop. First, what individual and social contexts should HCI researchers consider while promoting reflection? Second, what role can various forms of technology (e.g., just-in-time adaptive interventions, peer-support platforms) play in supporting and augmenting reflective practices? Through our workshop, we hope to bring together a community of multidisciplinary researchers and practitioners who aim to design and develop reflection interventions that are situated within the fabric of users' individual and social contexts.