This chapter seeks to help the reader understand how time interacts with rupture–repair processes in cognitive-behavioral therapy (CBT). The alliance emerges and evolves over time as a property of the therapeutic relationship, negotiated between patients and therapists throughout sessions and throughout entire treatments. It has been shown that during psychotherapy, the alliance is characterized by rupture–repair episodes which in return are predictive of treatment outcome and dropout. The theory of alliance rupture and repair focuses mainly on changes that occur within the same patient over time (within sessions and between sessions) and may answer questions such as “Are ruptures in one session associated with poorer alliance and outcomes after that session?” and “Can rupture-repair bolster against these detrimental effects?” A few studies have analyzed how rupture–repair evolves over time and results lend support to the influence of alliance ruptures on the future course of treatment. In response to a rupture, therapists may need to change their approach or intervention in order to work effectively. This stresses the importance of therapists’ awareness of ruptures during the therapeutic process. Immediate and expressive repair strategies can then be used to encounter alliance ruptures. Monitoring and feedback systems alerting therapists to ruptures or low alliance can be supportive. In this chapter, we offer take-aways for clinicians regarding rupture–repair dynamics. This chapter further provides clinical guidelines and examples for therapists helping them decide when, why, and how to intervene in the presence of a rupture.