The excellent sensitivity and specificity of right upper quadrant (RUQ) ultrasound for gallbladder pathology in patients with abdominal pain is heavily relied upon in routine diagnostic evaluation. The hour-to-hour timing of this test in a patient with fluctuating symptoms is not widely recognized as having a significant impact on its sensitivity. However, we present a case report describing the essential role of symptom-timed point-of-care ultrasound in making an elusive diagnosis of transient cholecystalgia in a patient with RUQ pain and congestive heart failure (CHF). This case also demonstrates an important etiology of RUQ pain in patients with CHF beyond that of congestive hepatopathy. A review of the related entities of acalculous cholecystitis, congestive hepatopathy, and diffuse gallbladder wall thickening is provided.