Climate change and poverty alleviation are examples of interconnected challenges propelling changes across environmental, social, cultural and political spheres. Interconnected challenges are characterized by multiple causality, feedback loops, non-linear dynamics. Transformations, as fundamental reconfigurations of social-ecological relations, are increasingly proposed as a strategy for tackling interconnected challenges. Transformations seem to require a move towards diverse, integrated, imaginative, anticipatory, dynamic forms of knowledge making. Although new forms of knowledge creation are indeed emerging in sustainability science and practice, this area of studies is yet to yield a coherent research framework for analyzing the contribution of these practices to transformations in social-ecological systems. The central aim of this thesis is to a) provide a theoretical framework and b) to explore and assess feasibility and effectiveness of concrete knowledge practices that could help governance actors to move towards forms of deliberate transformations in the face of interconnected challenges. Two empirical research papers based on a case-study in Coastal Kenya are presented. In these papers we approached the interconnected challenges of social-ecological trade-offs by engaging multiple knowledge practices (ranging from dialogue, to narrative scenarios, participatory modelling and ecological modelling) to create a space for imagination and deliberation amongst governance actors and scientists. Assessment of this process was performed with a mixed methods research design, including interviews, surveys, and participant observation. Results suggest that overall, these knowledge practices supported: a) development of systemic and collaborative mindsets (Paper 1); b) revision of core assumptions (Paper 1); c) the identification of key cross-scale tradeoffs that were previously not considered by governance actors (Paper 2). These results highlight the potential of these knowledge practices in fostering knowledge relevant for re-imagination and reconfiguration of social-ecological systems. I conclude by proposing that transformational knowledge practices present at least four key elements in that they are: plural and coproduced, affect change across scales, involve multiple ways of knowing and foster imagination.