Abstract The aim of this study is to investigate the characteristics and benefits of writing about personal experiences in prison. A variation of the classic writing paradigm was proposed to a sample of 93 male inmates in southern Italian prisons. Participants were left to write on any personal experience related to their condition and time in prison in 4 daily sessions. Measures of subjective well-being were collected across the sessions. Transcripts were analyzed through sentiment analysis. Cognitive and executive functioning indices (i.e., general cognitive abilities, working memory capacity, inhibition, and shifting) are included as covariates in our analyses on the evolution of well-being measures. Results showed that participants’ well-being improved across the sessions, independent of the emotional valence of the disclosed experience. This effect was partly modulated by the participant’s measure of working memory capacity. After an initial simplification, narrative productions appeared to increase their length and complexity. Our results support the idea that emotional disclosure in our sample of inmates contributes to social integration. Results encourage the adoption of writing procedures, as they are inexpensive and effective in supporting prisoners’ adjustment to prison life. Supplemental materials are available at https://www.press.uillinois.edu/journals/ajp/media/a_study_on_the_writing_paradigm/index.htm