Collaborative approaches to environmental governance have emerged as a method to tackle the multi-scalar, cross-jurisdictional challenge of maintaining and conserving geographically large and connected landscapes. To better understand the dynamics and outcomes of these collaborative initiatives, it is necessary to examine how collaborative environmental governance is structured, as well as the actors involved, their roles, goals, motivations, and the obstacles they face in achieving multi-scalar collaboration. In this thesis, I explore the Yellowstone to Yukon Conservation Initiative (Y2YCI), a bi-national collaborative conservation initiative that spans the Northern Rocky Mountains of North America. I examine the roles, goals, motivations, and obstacles to collaborative efforts towards natural resource management and conservation in the Y2YCI. I investigate the elements that enable and those that inhibit this collaborative partnership. These results are compared with a review of environmental governance frameworks in the academic literature on collaborative approaches to connectivity conservation and environmental governance more broadly. The outcomes of this research suggest certain elements important for successful large-scale conservation collaborations. For instance, both the frameworks and case study illustrate the importance of operating at multiple scales to encourage participation without requiring partners to change their individual goals and practices in order to collaborate. Additionally, involving the community and local-level partners is key to ensuring legitimacy, accountability, and trust with the larger collaborative initiative. Sharing knowledge amongst partners and with the broader community is one of the simplest ways to collaborate and is important for maintaining transparency and efficiency within the collaborative initiative. In most instances, elements considered significant in the academic frameworks were also considered to be significant amongst partners and staff members in this case study. A few notable exceptions include the use of a regional representative from the collaborative initiative, a facilitator, technology, and clearly defined goals and roles. This thesis provides a useful summary of the key elements for successful collaboration from the academic literature and frameworks. It also serves as a current and in-depth example for environmental managers and practitioners with lessons learned about the challenges and successes of engaging in collaborative governance across a large and dynamic social-ecological system.