Hierarchical linear modeling (HLM) techniques were used to explore interactions among individual and contextual variables and their effects on initial self-esteem levels and changes in these levels across the three years of middle school in a large, diverse sample (N=1804 students attending 23 schools). Interactions among race, social class, school socioeconomic status (SES), and contextual congruity were found to be particularly influential. Low-income European-American youth consistently experienced the lowest self-esteem levels and the sharpest declines during middle school. Social incongruity appears to play a crucial role in predicting such losses. These results highlight the need for further research employing similar techniques to explore how individual and contextual factors affect the development of self-esteem over the middle school years.