Background: Little is known about the attitudes and knowledge of oncologists who discuss financial toxicity with patients compared with those who do not. We assessed perceptions of the oncologists’ role in discussing out of pocket (OOP) costs and financial stress (FS) to inform quality improvement strategies in the management of financial toxicity. Methods: We surveyed 45 practicing medical oncologists at a large academic medical center in 2019 using Likert scale responses. Questions covered three domains; self-perceived knowledge of financial issues related to care, practice of cost discussions with patients, and perceived ability to navigate toward solutions related to FS. Results: Fifty-three percent of oncologists felt comfortable discussing OOP costs, but only 42.5% discussed FS with patients. Over half (55%) lacked confidence they could help patients experiencing FS from treatment. These providers were less likely to ask about FS than those who were confident (r0.416, p0.004). Perceived knowledge among many was low: 48% felt they had little to no knowledge of OOP treatment costs, 33-37% had little to no understanding of how private or public insurance covers treatment respectively, and 60% reported low knowledge of point of care (POC) resources. Those who ask patients about FS reported higher perceived knowledge of insurance (public r0.47, p < 0.001, private r0.452, p 0.002) and POC resources (r0.392, p 0.007), but not more knowledge of OOP cost. Three factors were associated with increased confidence in the ability to help patients; higher knowledge of POC resources (r 0.379, p 0.01); having changed a treatment because of cost within the past year (r 0.395, p 0.047), and years in practice (r 0.329, p 0.047). Conclusions: Many oncologists lack confidence that they can help patients with financial issues, particularly early on in their career. Providers who lack confidence that they can help their patients appear less likely to ask patients about financial stress. Those who do ask about financial stress report higher self-perceived knowledge of insurance coverage and POC resources. This suggests that quality improvement efforts aimed at improving education and resources for providers to help navigate financial toxicity are needed.