The way towards sustainability for the collective environment of university activities has a crucial role in achieving broader institutional sustainability goals in education, research and projects, both inside and outside university walls, particularly concerning its impact on society. This chapter discusses obstacles and opportunities for the sustainable transformation of the university environment, considering the ongoing process and investments of the Pontifical Catholic University of Rio de Janeiro in the sustainability of its Campus, especially concerning the application of its brand-new Socio-environmental Agenda (an institutional planning instrument built in participatory process over two years). The chapter analyzes the obstacles to implementing the Agenda, regarding (1) governance, (2) teaching and curriculum, (3) research, and (4) projects in all eleven new agenda items, defined as basic topics (water; biodiversity; energy; waste; constructed and living spaces; mobility) and crossing topics (education, health, communication, information technology and resilience to climate change). Definition of priorities, governance strategies, continuous monitoring, funding, new applications of technology and resisting inadequate paradigms are some of the obstacles observed, offering contributions to the exchange of good practices for the community of higher education worldwide.