The differential diagnosis of ring-enhancing brain lesions in a patient with metastatic malignancy may initially seem straightforward, and easily attributed to brain metastases. On rare occasions, the physician needs to avoid anchoring bias by re-evaluating the entire clinical context in which these ring-enhancing brain lesions are found. We report a case of cerebral toxoplasmosis mimicking brain metastases in a patient with metastatic cancer and without a prior history of human immunodeficiency virus. A 65-year-old lady with a recently detected relapse of her endometrial carcinosarcoma presented with a 2-week history of fever with no localising symptoms or signs of infection. The initial investigations were unremarkable. She had daily fever despite empirical broad-spectrum antibiotics. A positron emission tomography-computed tomography (PET-CT) was performed to evaluate the pyrexia of unknown origin, which showed metastatic deposits in the pelvis. A magnetic resonance imaging (MRI) of the brain was subsequently performed due to fluctuating mentation, which reported metastatic disease to the brain. Her pyrexia of unknown origin was attributed to malignancy-related fever. The medical oncologist was cautious about starting systemic treatment because the PET-CT had FDG-avid diffuse ground glass opacities in both lung fields, and requested for a bronchoscopic evaluation, which returned positive for Pneumocystis jirovecii. In light of this new finding, a multi-disciplinary discussion and a review of the brain MRI were undertaken, during which it was concluded that the likelihood of cerebral toxoplasmosis was much higher than brain metastases. She was treated with high dose trimethoprim-sulfamethoxazole for both P. jirovecii pneumonia and cerebral toxoplasmosis, with clinical and radiological improvement. This case highlights the importance of (a) clinical input in interpreting imaging findings, (b) entertaining the possibility of multiple concurrent pathologies explaining a patient’s symptoms, (c) being open to alternate diagnoses when new information surfaces even though the current working diagnosis is the most plausible and (d) multi-disciplinary communication when faced with diagnostic difficulty