Collusion is an unharmonious bond between the doctor and a patient or between patients and caregivers. This case report exemplifies one such experience and highlights the hurdles we face when dealing with collusion. A 31-year-old woman was diagnosed with rectal carcinoma during her pregnancy and underwent diversion colostomy (for intestinal obstruction) followed by neoadjuvant chemoradiation after delivery. Later, she was diagnosed with metastatic disease and was under palliative care. The family always had a negative association with cancer and chose to withhold information from the patient throughout the treatment trajectory. Collusion and lack of information can be a factor for persisting total pain. While caregivers desire to protect the patient from the distress of a life-limiting diagnosis, invariably it causes more anguish than comfort. Oncology professionals need to consider collusion as part of our sociocultural fabric and develop a strategy to negotiate and improve the care.