This chapter will help therapists consider how the cultural encounter in the room may impact rupture repair processes in cognitive-behavioral therapy (CBT). The CBT literature largely ignores the role of culture in ruptures, which is perhaps indicative of what is happening in therapy offices. Cultural context is sometimes just reduced to the patient’s race or country of origin while it should be treated as an intricate system that consists of the patient’s intersecting identities, the therapist’s identities, their relational and power dynamics in the room, their previous relational experiences and resulting assumptions, and the context around them. This context includes immediate environmental influences such as the institution, power structures, and treatment circumstances, as well as wider societal events, media influences, and zeitgeist. This chapter helps therapists increase cultural attentiveness and avoid dismissing cultural dynamics as resistance, lack of cooperation, emotional instability, pathology, enmeshment, dependency, transference, and various “othering” labels. The clinical examples and dialogues illustrate how ruptures occur in the interrelation of two people and their context/situation, thus replacing the simplistic view of the client or patient being “difficult.” The chapter will explore how therapists’ own behaviors, however unintentional, may contribute to the ruptures. However, we also suggest moving away from assigning blame in ruptures, and instead, moving toward taking responsibility for considering context. To facilitate that, the chapter will also provide guidelines for maintaining cultural reflectiveness in recognizing and resolving ruptures.