Building relationships and community collaborations--especially on an institutional level--is a slow and long-term process. These types of innovative, experimental, and long-term collaborations with community organizations and groups often lead art institutions to reflect on the value and place of their institutional structures when engaging in collaborative projects that strive for political engagement and community development. Taking into consideration the notions of risk, conflict, power, language, and funding structures, this article names the challenges to and analyzes the potential for collaborative practices between art institutions and non-art community groups and organizations within program development and community engagement work. It argues that to truly "collaborate" art institutions must make a break from long-standing traditions and embrace very new ways of thinking about, talking about, and doing work in the sometimes rarefied world of Art.