A 51-year-old man with a history of nephrolithiasis presented to the Emergency Department after a sudden onset of left-sided groin pain and syncope. At presentation, he described his pain as similar to prior renal colic episodes. At his initial assessment, point of care ultrasound (POCUS) was used, which revealed findings consistent with obstructive renal stones, as well as a substantially enlarged left iliac artery. Computed tomography (CT) imaging confirmed the comorbid diagnoses of left-sided urolithiasis and a ruptured isolated left iliac artery aneurysm. POCUS facilitated expedited definitive imaging and operative management. This case highlights the importance of performing related POCUS studies in reducing anchoring and premature closure bias.