Transparency—the observability of activities, behaviors, and performance—is often treated as a panacea for modern management. Yet there is a conundrum in the literature, with some studies suggesting that transparency may benefit group creativity and others suggesting that privacy may do so. A similar conundrum exists regarding the effects of different social capital types—structural holes vs. network cohesion—on group creativity. Enterprise social media (ESM) provide a unique opportunity to solve these conundrums by allowing groups to be “transparent” (non-group members can observe and/or participate in group activities) or “private” (group members and activities are hidden from the community) and enabling groups to develop distinct social capital structures. Using data from 28,083 written interactions produced by 109 transparent and 106 private groups in an ESM of a multinational design firm, we found strong support for our contingency hypotheses that both transparent and private groups may produce high levels of creative dialogues, yet in different forms. Specifically, expansion-focused creative dialogues— those focused on combining or expanding existing concepts—emerge in transparent groups, but only when the group’s social capital is characterized by structural holes. Conversely, we found that reframingfocused dialogues—those focused on challenging and rethinking—emerge in private groups but only when the group’s social capital is characterized by network cohesion. Theoretically, these findings can help to solve the conundrums in the literature on group creativity and shed light on the role of ESM use in this context. Practically, our findings offer a critical reflection o contemporary initiatives for increasing transparency, whether through physical design or digital transformation.