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Alexithymia has been associated with poor outcomes in psychotherapy. This association has been attributed to a difficulty in patients expressing emotions, engaging in emotional tasks and also poor therapeutic alliances. This study aims to better understand alexithymic patients in psychotherapy. A multiple case study design was used. Cases were selected from a larger research project considering their alexithymia level and outcome status, based on the reliable change index and the client perspective on change. Four cases are presented: with and without alexithymia with good and poor outcome. The therapeutic alliance was included as a process measure, evaluated from both client and therapist. At the end a semi structured interview was conducted with both participants, individually. The analysis concerned the integration and triangulation of the therapist and client experience for each case. Each patient was briefly presented and then a focus was made regarding the perception of both participants on the therapeutic alliance and the emotional processing and change process of the client. Both alexithymic cases and the non-alexithymic poor outcome case showed difficulties in the therapeutic alliance, especially from the perspective of the therapist. In these cases, emotional impairments may have contributed to a poor therapeutic alliance, impacting on the outcome. We suggest that a great focus on the therapeutic alliance with alexithymic patients may increase the quality of treatment and it may be more useful for case conceptualization to consider each feature of the alexithymia construct individual.