The present study sought to further understand patients’ crying experiences in psychotherapy. We asked 64 clinicians to randomly request one patient in their practice to complete a survey concerning crying in psychotherapy as well as a measure of therapeutic alliance. All clinicians provided information regarding their practice and patient diagnostic information. Fifty-five (85.93%) patients cried at least once, and 18 (28.1%) had cried during their most recent session. Patients’ frequency of crying episodes in therapy was negatively related with psychotic level of personality organization, while patients’ tendency to feel more negative feelings after crying was positively related to lower levels of personality organization. Patients’ feeling more in control after crying was positively related with an interpersonal therapeutic approach, while patients’ perception of therapists as more supportive after crying was positively related to a psychodynamic approach. Patients’ tendency to experience more negative feelings after crying was significantly related with both lower levels of personality organization and patients’ perception of the therapeutic alliance as weak. In regard to their most recent crying event in treatment, therapeutic alliance was related to gaining a new understanding of experience not previously recognized by the patient. Further, patients’ experiences of having never told anyone about their experience related to a crying episode, as well as their realization of new ideas and feeling of having communicated something that words could not express was positively related to the goal dimension of alliance. Patients’ perception of crying as a moment of genuine vulnerability, greater feelings of self-confidence and self-disclosure as well as having had a therapist response that was compassionate and supportive, was positively related with the bond dimension of alliance. Clinical implications and future research directions regarding patient crying experiences in psychotherapy are discussed.