The last quarter century saw a restructuring of employment, production and trade and a dramatic decline in union membership and density levels. There are many explanations for this, including the hostile industrial relations framework imposed by many governments, but there have been other factors such as the growth of new non-unionized industries that often rely on casualised labour; new attitudes to unions by younger workers; a political/cultural decline in the workers' movement under neo-liberalism; and an inability by many unions to adapt to these changes. Now dramatic economic changes arising from the global financial crisis that will see increased unemployment and further industry restructuring, along with the restructuring and re-skilling implications of climate change, pose new challenges for trade unions. Drawing on research with senior Australian union officials about the movement's education and training activities this paper considers the relevance of the adaptive systems literature for understanding the operational environments facing unions as they become larger more complex organizations. It considers the existing suite of education activities with reference to Illeris' tension field and the literature of union renewal that emphasises the need to develop new solidarities and therefore a broader conception of education, learning and development. (Contains 2 notes.)