In this article, we present two medicolegal cases illustrating medical and diagnostic pitfalls that can lead to litigation for missed testicular torsion. Testicular torsion (TT) is a urologic emergency with potentially devastating consequences and costs, for providers and patients alike. TT occurs in approximately 4.5 per 100,000 males under the age of 25. While uncommon, TT is the third most common cause of medical malpractice suits in this demographic. As a consequence of varying presentations and physical exam findings, and diagnostic imaging subject to individual interpretation, this time-sensitive diagnosis may be missed by emergency department providers. Delays in diagnosis significantly increases the morbidity associated with TT, and 31.9%-41.9% of such cases result in testicular loss. The average reported settlement for TT malpractice litigation is $60,000. This article discusses two actual malpractice cases involving TT and provides insight and caveats to ensure an optimal evaluation and diagnostic approach to this often-elusive condition.