This study investigates the influence of personality on adjustment to a particular life transition, community relocation. Participants were 285 women (average age = 69.5) who were interviewed once before they moved, and then multiple times after the move. Within the context of this multiwave design, personality traits were used to predict changes in depressive symptoms (DS) and self-esteem (SE) across the move. Neuroticism and Openness to Experience predicted increases in DS over time, whereas Extraversion and Openness predicted increases in SE. Stressful reactions to the move and sense of mastery about the move partially mediated these effects. The study documents the dynamic influence of personality on positive and negative aspects of adjustment and investigates differing routes through which such effects occur.