The practice of conservation is challenging due to the complexity, uncertainty, and dynamism of social and ecological systems. There is often a gap between the acquisition of conservation science knowledge and the application of on-the-ground actions; this has been referred to as the “science-action gap.” Bridging this gap has become increasingly important given the complexity of most environmental problems and the need to involve a broad range of stakeholders. Efforts to fill this gap have resulted in a proliferation of decision support systems used to address spatial management strategies (such as connectivity planning), identify areas of priority for certain management strategies (construction of crossing structures), and to assess trade-offs. In this chapter we provide an overview of decision support systems applied to connectivity planning and share “lessons learned” from our collective experiences in applying these tools in real-world settings.