Presenting for a variety of reasons, a caregiver that exhibits behaviors that make them challenging to work with (e.g., stress, hostility, questioning, psychopathology) may prevent or impede gains when working within the context of a child-focused family therapy (i.e., therapy involving caregivers in the planning and implementation of child-centered treatments). Although some work has addressed the challenging patient, little research is available that has concisely translated such information into considerations, recommendations, and tips for preventatively facilitating strong rapport or managing any recognized challenging behaviors that the caregiver of the identified child patient may exhibit. For this reason, the current article aims to provide an integration of literature and clinician experience to provide practice-oriented considerations for those conducting child-focused behavioral or cognitive-behavioral family-based interventions. Discussion begins by outlining the initial contact and preparation with the family before reviewing techniques for ongoing treatment. Considerations for situations in which hostility, confrontation, or anger arises toward the clinician, as well as the patient (i.e., the child) are then discussed. Finally, clinician-focused factors to consider are examined. Effectively negotiating challenging caregiver behaviors within the context of a child treatment can enable clinicians to provide the often necessary and beneficial treatment that would otherwise not be possible. Through integration of proposed preventative and management considerations, a clinician may facilitate a strong relationship with the family, work to repair any ruptures in the relationship, and negotiate challenges brought forth by the challenging caregiver to avoid therapeutic disruptions or premature termination.