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The current, unprecedented rate of human development is causing major damages to Earth's life-support systems. Therefore, the need for transitions toward sustainability in the use of natural resources and ecosystems has been extensively advocated. To be successful, such transitions must be guided by a sound understanding of the architecture of the policy and institutional designs of both the process of change and the target outcome. Here, we contribute to current research on the institutional conditions necessary for successful transitions toward sustainability in social-ecological systems, addressing two interrelated theoretic-analytical questions through an in-depth case study focused in the Doñana region (Guadalquivir estuary, southwest Spain). First, we focus on the need for enhanced historical causal explanations of social-ecological systems stuck in maladaptive rigidity traps at present. Second, we focus on the explanatory potential of several factors for shaping maladaptive outcomes, at two different levels of analysis: political-economic interests, prevailing discourses and power, at a contextual level, and institutional entrepreneurship, at an endogenous level. In particular, we address that explanatory potential when the core logic of path dependence fails to predict maladaptive outcomes in a historical, evolutionary perspective. When this occurs, such outcomes are often qualified as unexpected, hence subject to contingency, because of their divergence from purported superior, optimal alternatives. We argue that contingency can be modulated away from randomness and better characterized as unpredictability, through the systematic inclusion of the mentioned factors into analysis. This would, in turn, increase our capacity to inform future policy and institutional transitional designs toward sustainability. [ABSTRACT FROM AUTHOR]