Although numerous studies have investigated the relationship between the therapeutic alliance and dropout, most have focused on the relationship between alliance quality and psychotherapy outcomes. Objective: To compare sessions with therapeutic alliance ruptures and two sessions prior to treatment dropout (pre-dropout) in terms of rupture subtypes, psychotherapists' behavior, attitudes, and session content. Method: We implemented quantitative methods to select the sessions and qualitative methods to analyze them. We analyzed 16 temporary rupture sessions from 12 therapist-patient dyads and 16 pre-dropout sessions from 8 different therapist-patient dyads. The sessions originate from clinical psychology Master's or Doctoral students under supervision in either cognitive behavioral or schema therapy. Pre-dropout sessions were considered unrepaired rupture sessions while rupture sessions were subsequently repaired. Results: Results revealed apparent differences and similarities between the session types in positive and negative psychotherapist behaviors, content intensity, and the type and frequency of ruptures. We explored three new rupture subtypes: attributing positive developments to other sources, indirect speech, and sarcastic hostility. Conclusions: A striking implication is that the frequency of positive and negative psychotherapist behaviors, ruptures, and session content is more likely to decrease in the pre-dropout sessions than in the temporary rupture sessions.