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Jeremy Safran and his research group suggest that rupture-repair processes are important for the therapeutic change in patients with personality disorders. In this exploratory study, we describe alliance ruptures and resolutions on a session-by-session basis in a clinical sample of adolescents with Borderline Personality Pathology (BPP). Three research questions are addressed: i) Is there a typical trajectory of alliance ruptures over treatment time? ii) Which rupture and resolution markers occur frequently? iii) Which rupture markers are most significant for the therapeutic alliance? Ten patients who presented with identity diffusion and at least three Borderline Personality Disorder criteria were studied and treated with Adolescent Identity Treatment. Alliance ruptures and resolutions were coded in 187 therapy sessions according to the Rupture Resolution Rating System. Mixed-effect models were used for statistical analyses. Findings supported an inverted U-shaped trajectory of alliance ruptures across treatment time. The inspection of individual trajectories displayed that alliance ruptures emerge non-linearly with particular significant alliance ruptures appearing in phases or single peak sessions. Withdrawal rupture markers emerged more often compared to confrontation markers. However, confrontation markers inflicted a higher impact or strain on the immediate collaboration between patient and therapist compared to withdrawal markers. Clinicians should expect alliance ruptures to occur frequently in the treatment of adolescents with BPP. The findings support the theory of a dynamic therapeutic alliance characterised by a continuous negotiation between patients and therapists.