The Big Five Personality is one of the theories of personality that consists of five personality dimensions, namely: Agreeableness, Openness to New Experience, Extraversion, Neuroticism and Conscienstiousness. Thirty-five prisoners of cases of narcotics and drug trafficking into subjects in this study. In testing the assumptions of normality of data, showed that the data were normally distributed. This is indicated by the value of significance (p-value) greater than 0.05. As for the correlation test, showed that Openness to Experience significantly positively correlated with Psychological Wellbeing (r = 0.504; p = 0.002). Extraversion significantly positively correlated with Psychological Wellbeing (r = 0.420; p = 0.012). Agreeableness positively correlated significantly with Psychological Wellbeing (r = 0.620; p = 0.000). Constinousness significantly positively correlated with Psychological Wellbeing (r = 0.473; p = 0.004). Neuroticism is negatively correlated significantly with Psychological Wellbeing (r = - 0.479; p = 0.004). The purpose of quantitative research with correlational approach is to know the relationship between the Big Five personality dimensions with Psychological Wellbeing on inmates in Prisons Women Class II A Malang. Further research is expected to contribute to the Women's Prison Class II A Malang in order to carry out the task of coaching the inmates. Conclusions from the analysis of the data is that the four dimensions of personality Big Five Personality significantly positively associated with psychological well-being. Except for Neuroticism personality dimensions are significantly negatively associated with psychological well-being.