Much emphasis has been placed on the importance of learning to support collaborative environmental management and achieve sustainability under conditions of social-ecological change. Yet, on-going struggles to learn from experience and respond to complex social-ecological conditions reflect an emerging paradox. Despite widespread support of learning as a normative goal and process, core concepts, assumptions and approaches to learning have been applied in vague and sometimes uncritical ways. Greater specificity with respect to learning goals, approaches and outcomes is required. In response to this gap, we examine five dimensions of the learning paradox in the context of adaptive co-management, where the learning and linking functions of governance are stressed: (i) definitions of learning; (ii) learning goals and expectations; (iii) mechanisms by which learning takes place; (iv) questions regarding who is involved in the process of learning; and (v) the risks and ethical ambiguities faced by different actors expected to willingly participate in a learning process, whether formal or informal. Lessons from experience with a series of cases from the global North and South illustrate the implications of these dimensions. Resolving the dimensions of this learning paradox will require greater attention to capacity-building, recognition of the role of risk, and consideration of how incentives could be used to encourage learning. Further consideration of the role of power and marginality among groups participating in the learning process is also needed, as is more systematic evaluation to monitor and measure learning outcomes.