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This article explored the risks and rewards of designing and teaching in an externship program, the goals one might have, and the methods one might use. We have argued that it is important to pay attention to the principles of intentional design when developing an externship program. In particular, we have identified and challenged the assumption that skills development must be the predominant goal for externships. This is a common assumption on the part of legal education regulators in our respective home countries, the USA and Australia, as well as in England and Wales. Skills development can, but does not have to, be a focus for every externship. If it is to be a focus, the targeted skills should be articulated as clearly and specifically as possible. Students must learn the theory and methods behind the skills to be used in the placement, either through appropriate pre-requisites, a skills-focused classroom component, or a clear understanding that the placement supervisor will be able to impart both the relevant theory and methods. Then the reflection component also must be designed to enhance students’ acquisition of the identified skills. We have explored how this can be done with either the “tailor-made” or the “retail” externship structure. However, we believe the regulatory focus on skills has obscured the important values that can be acquired through a well-designed and well-taught externship.