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Human beings have an amazing capacity to learn new skills and adapt to new environments. However, several obstacles remain to be overcome in designing paradigms to broadly improve quality of life. Arguably, the most notable impediment to this goal is that learning tends to be quite specific to the trained regimen and does not transfer to even qualitatively similar tasks. This severely limits the potential benefits of learning to daily life. This review discusses training regimens that lead to the acquisition of new knowledge and strategies that can be used flexibly across a range of tasks and contexts. Possible characteristics of training regimens are proposed that may be responsible for augmented learning, including the manner in which task difficulty is progressed, the motivational state of the learner, and the type of feedback the training provides. When maximally implemented in rehabilitative paradigms, these characteristics may greatly increase the efficacy of training.