In this article, we examine how the different attachment patterns enable or hinder the resolution of ruptures in the therapeutic alliance. We try to show that secure and insecure patients alike may experience ruptures in the therapeutic alliance, but that their ability to participate in resolving such ruptures differ markedly. Recent findings with the Patient Attachment Coding System (PACS) show that attachment classifications manifest in psychotherapy as distinct ways of communicating about present internal experience. Secure patients disclose their present experience openly and invite attunement from the therapist, while insecure patients either minimize their contributions to the dialogue (avoidant) or the contributions of the therapist (preoccupied). Using examples from session transcripts, we demonstrate how secure patients are particularly responsive to resolution strategies that focus on here-and-now experience, while insecure patients’ characteristic ways of communicating pose significant challenges to the resolution process.