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We present work on support for collaborative reflection. So far, most research has been on individual reflection or reflection in educational context and therefore, and little is known on designing support for collaborative reflection. In three studies of using an application for collaborative reflection support, we analyzed usage data as well as material from interviews and observations. Our results show that there were different ways in which the application impacted reflection in the workplace and that besides positive effects we found open issues in reflection support. Based on these results, in the paper we present insights on and design challenges for collaborative reflection support as well as potential solutions for these challenges. We relate these findings to a model of collaborative reflection support and emphasize that support needs to be understood as socio-technical support if it is to succeed in practice.