Cancer-associated thrombosis (CAT) is a major cause of morbidity and mortality in patients with cancer. The management of special situations—including recurrent venous thromboembolism (VTE), thrombosis at unusual sites, and central venous catheter-associated thrombosis (CVC-AT)—remains particularly challenging because of the limited availability of high-quality evidence. This narrative review synthesizes recommendations from major international and Spanish clinical practice guidelines and expert consensus documents, including those from SEOM, ESMO, ASCO, NCCN, ITAC and SEMI, to provide a structured framework for the management of these complex scenarios. Our analysis identified substantial heterogeneity across guidelines, particularly regarding anticoagulant selection, dosing strategies, and treatment duration. Although some convergence exists in the management of CVC-AT, important discrepancies and evidence gaps persist in areas such as splanchnic vein thrombosis, hepatic impairment, central nervous system involvement, and recurrent VTE despite treatment. In many cases, recommendations are based primarily on expert opinion rather than robust trial data, and several clinical scenarios are addressed by only a limited number of guidelines. These findings underscore the need for more standardized management strategies and prospective clinical studies to better inform decision-making in daily practice. Overall, this review highlights the growing importance of individualized anticoagulant management aimed at balancing thrombotic and bleeding risks in high-risk oncology patients, thereby helping to bridge the gap between expert consensus and evidence-based precision anticoagulation.