Caucusing, as a social justice activity, is traditionally implemented to provide an insider space for marginalized persons to share experiences and build a space for belonging and safety by excluding those who hold privileged identities. Within a particular event that combines privileged and oppressed, experiences are uneven, with insiders experiencing inclusion, while outsiders have a largely isolating experience, although intended to be a place to interrogate privilege. It is not an activity to build community across identities, nor is it the intention. Through expansive reflection on a course activity, the authors share their experience of an updated caucusing activity, a three-part undertaking that first holds caucuses where all students participate, subsequently holds cross-identity dialogues, and then dialogues are repeated with different groupings. Informing this article are the authors' separate and dialogic reflections, activity evaluations and follow-up comments by students. Results reveal high potential for building belonging and community within and across identities, potentially relevant to numerous service professionals. Caution exists when groups have low levels of engagement with each other and trusting experiences with each other and the instructor. A less successful version of this activity occurred in a part-time program which suggests this caution is warranted.