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Even though environmental contexts have been associated with personality development, little attention has been paid to individuals’ psychological perceptions thereof. Basic psychological needs theory assesses environments based on their levels of autonomy, competence, and relatedness support. In order to better understand the factors that drive personality development we related the support of basic psychological needs (BPN) and the individual importance ascribed to BPN support to Big Five personality development 1.5 years later. We focused on the context of the first job in a longitudinal study of young Germans (NT1 = 1,886; MageT1 = 18.41). Based on theory and previous research we derived multiple hypotheses and tested them simultaneously against each other with an information theoretic approach including response surface analyses. Results differed across the Big Five: Controlling for personality at T1, people who ascribed greater importance to BPN support, had higher perceptions of BPN support, and who had an incongruence between the two at T1 were higher in emotional stability and extraversion at T2. The pattern was more complex for openness, whereas individuals ascribing more importance to BPN support at T1 were more agreeable and conscientious at T2. Findings are discussed for theory and future research of personality development