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Transitions of young people from school to employment, further education or training have been a focus of government policy in the UK for at least the last three decades. Since the late 1990s, numerous policy initiatives have been introduced by New Labour in an attempt to reduce social exclusion through the increased participation of young people in work-related training. This paper reports on a mixed-methods research project exploring Entry to Employment (E2E) provision in the north of England. It outlines the experiences of Connexions practitioners working with learners and staff at four E2E providers and illustrates the complexities involved with young people's transitions to and from E2E programmes. The paper shows that a marketised system driven by targets and funding constraints can compromise the ability of practitioners to best meet the needs of young people struggling with often difficult circumstances.