This chapter focuses on resolving alliance ruptures with patients whose personality style includes characteristics such as pervasive avoidance, obsessive rumination, circumscribed and/or vague communication, and behavioral and emotional over-control. Patients’ patterns of avoidance and perseveration may make it difficult for their therapists to understand them well and/or establish or maintain a connection. At times the therapeutic alliance undergoes a rupture, perhaps resulting from the patient’s feeling excessively intruded upon by the therapist’s probing questions, or because the therapist is not providing assurances and guarantees, as well as other subtle points of tension. This sort of problem has been described in the literature as a withdrawal marker, in which there is little or no explicit conflict between therapist and patient, but the patient implicitly expresses discomfort with therapy by providing minimal information, offering little feedback, and generally dis-engaging. The patient may fail to keep appointments and/or return phone calls, sometimes dropping out of treatment and out of touch altogether. Drawing from quantitative and qualitative data from a major clinical trial of Beckian cognitive therapy for avoidant personality disorder and obsessive-compulsive personality disorder, this chapter offers guidelines on how to recognize, empathically understand, and repair withdrawal ruptures with patients who exhibit overcontrolled behaviors and emotions. The chapter will include clinical examples of therapists recognizing alliance ruptures and taking corrective action to foster a sense of collaboration and good will, utilizing competencies such as self-awareness, self-regulation, compassionate communication, and problem-solving.