Mitral regurgitation (MR), one of the most common valvulopathies, occurs in at least 10% of the individuals older than 75 years. The long-standing volume overload occurring in severe MR inevitably leads to left ventricular (LV) enlargement and dysfunction; untreated, severe MR can progress to heart failure and death. Hypotension following separation from cardiopulmonary bypass after mitral valve intervention should alert an anesthesiologist to consider a myriad of differential diagnoses. This includes, but is not limited to, afterload mismatch, which can contribute to severe LV dysfunction, even in patients with seemingly normal preoperative ejection fraction. We present a case of acute on chronic biventricular failure after mitral valve repair due to afterload mismatch and discuss its management intraoperatively. Admittedly, identifying the causes of hypotension to guide treatment after mitral valve surgery in patients with severe MR is challenging. High index of suspicion and transesophageal echocardiogram guidance are important for prompt diagnosis, increasing the likelihood of successful outcomes with appropriate clinical management.