This study used qualitative methods to explore psychotherapists' experiences conducting at-home psychotherapy with older adults (60 + years) with long-term care needs and depression. We conducted semistructured interviews with 16 female psychotherapists (26-70 years old) who delivered at-home cognitive behavioral therapy to home-living older adults with long-term care needs and depression. We additionally conducted 10 patient case studies. Using an adaption of the methodology of grounded theory, we iteratively developed a hierarchical model. Results showed that psychotherapists experienced three dilemmas: (a) pushing for change versus acknowledging limitations, (b) providing help versus maintaining boundaries, and (c) being a guest in the patient's home versus the host of a psychotherapy session. The absence of a shared understanding of therapy and confrontation with patients' existential suffering intensified the experience of the dilemmas. The dilemmas generated professional self-doubt and negative emotions, which in turn triggered a reflexive process and ultimately participants' professional development. Participants found a way to integrate drives initially perceived as mutually exclusive, and further developed their professional self-image and therapeutic techniques. We interpret the dilemmas as reflecting difficulty reconciling the "curing" and "caring" treatment paradigms. Practice and support managing the three dilemmas along with reflection on the curing paradigm, views on old age, and fear of existential suffering should be part of qualifications for psychotherapists working with older adults in need of care. Cooperating with other care providers may relieve the pressure on psychotherapists to provide forms of support that could lead to overburden and impede therapeutic progress. (PsycInfo Database Record (c) 2023 APA, all rights reserved).