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To address complex social challenges, it is widely recognized that leaders from public, for-profit, and civic organizations should join forces. Yet, well-intended collaborators often struggle to achieve alignment and fail to gain traction in their joint efforts. This article proposes the concept of "entry points" as a key milestone in a collaboration's early stages. Using a unique set of rich, longitudinal data, we examine how ten cross-boundary teams with representation from ten city governments in North America and Europe searched for these entry points (i.e., opportunities for focused action to advance learning and progress towards their collective goals). Based on systematic coding, we propose factors that impeded or enabled the teams' abilities to find entry points in their collaborative work. The paper contributes to literatures on cross-boundary collaboration, problem-oriented governance, and paradoxes in organizational behavior, and it offers an analytic framework to help cross-boundary collaboration practitioners identify their entry points.