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The aim of this investigation was to determine the impact of the timing and number of school transitions on young adolescents’ subsequent adjustment. Three groups of adolescents (total N = 253) were compared: those making a single early school transition prior to sixth grade, those making a single later transition prior to seventh grade, and those making a double transition prior to both sixth and seventh grades. Adjustment was assessed in terms of course grades and self-image. Negative effects were found for both early and repeated school transitions, with the double transition being especially debilitating. In addition, effects were seen primarily with course grades. Few gender differences were observed in the response to early and double transitions, but those that emerged suggest that girls may be more adversely affected than boys.