Purpose of Review <p>This review article examines the evolving evidence on cancer recurrence and new malignancy risk associated with disease-modifying antirheumatic drugs (DMARDs), including TNF inhibitors, rituximab, IL-6 inhibitors, and JAK inhibitors, in patients with rheumatoid arthritis and a prior malignancy.</p> Recent Findings <p>Conventional synthetic DMARDs are generally considered safe in patients with a history of cancer, with earlier concerns about skin and hematologic malignancies largely disproven. Hydroxychloroquine, sulfasalazine, and leflunomide similarly show no consistent cancer risk. Biologic DMARDs, including TNF inhibitors, rituximab, and abatacept, have not been linked to increased cancer recurrence, though caution is advised in patients with a history of skin cancer. Despite supportive evidence, bDMARD use has declined following cancer diagnoses. JAK inhibitors, however, have shown increased risk of lung cancer in older patients with cardiovascular risk factors, prompting cautious use until more data is available.</p> Summary <p>Although large population clinical trials are lacking, current evidence does not demonstrate any increased risk with initiation of csDMARDs, TNF inhibitors, and rituximab in RA patients with a history of cancer. Abatacept and IL-6 inhibitors may also be reasonable options but require further data. JAK inhibitors should be used cautiously until more reliable data becomes available. These findings support cautious but not prohibitive use of bDMARDs in RA patients with a history of cancer, emphasizing individualized risk assessment and shared decision-making. Further high-quality, prospective studies are needed to guide therapy in this complex clinical population.</p>