Crying may be a beneficial experience and reflect a patients’ involvement in the therapeutic work, as well as a potential indicator of the healing process. This study explored the relationships between patients’ crying experience in therapy, their perception of working alliance and therapeutic change, as well as considering the role of attachment styles. One hundred six patients completed a survey about crying in psychotherapy and self-report measures for assessing working alliance, therapeutic change, and attachment styles. Concerning general crying experiences, results showed that when patients’ crying (even if painful) was followed by more positive or less negative emotions (i.e., a sense of relief), they perceived the working alliance more positively and therapeutic change as enhanced. Similarly, regarding their most recent crying episode, patients’ feeling of crying as a positive (albeit often painful) experience was related with a better perception of working alliance and therapeutic change. In relation to variance explained by patient attachment style, our results are quite limited and secondary to the findings on crying-related experiences, working alliance and therapeutic change. However, when attachment style did contribute significantly to a regression model, results indicated that for patients with high dismissing attachment concerns, crying in a context of a good working alliance may represent both a useful process for reducing negative emotions and an indicator of good therapeutic outcome. Clinical and empirical implications are discussed in terms of the relevance of the therapeutic crying experience on the quality of working alliance and therapeutic change. (PsycInfo Database Record (c) 2021 APA, all rights reserved)