Background/Objectives: Rock climbing is becoming more popular, leading to an increased focus on diagnosing and treating related injuries. Finger pulley and flexor tendon injuries are common among climbers, with the A2 pulley being the most frequently affected. High-resolution ultrasound (US) is the preferred method for detecting pulley injuries. This study aimed to determine the reliability and validity of US in identifying anatomical landmarks for diagnosing A2 pulley ruptures. Methods: This study was cross-sectional, involving 36 fingers from 4 cadaver arms. A Canon Aplio i800 US machine was used to measure two anatomical landmarks: the midpoint of the proximal phalanx and the distal edge of the A2 pulley. For the first anatomical landmark, the length of the proximal phalanx (PP distance), and for the second landmark, the distance between the distal edges of the proximal phalanx and the A2 pulley ("A" distance), were measured. Measurements were performed by two sonographers and compared to a digital caliper measurement taken post-cadaver dissection. Observers were blinded during measurements to ensure unbiased results. Results: Overall PP distance measured by US (O1: 37.5 ± 5.3 mm, O2: 37.8 ± 5.4 mm) tended to be shorter than caliper measurements (O3: 39.5 ± 5.5 mm). The differences between sonographers were minimal, but larger when compared to caliper measurements. High reliability for PP distance measurement was observed, especially between sonographers, with an ICC average of 0.99 (0.98, 1.00). However, reliability was lower for the "A" distance, with significant differences between US and caliper measurements. Regarding validity, US measurements were valid when compared to caliper measurements for PP distance, but not as reliable for the "A" due to wider confidence intervals. While US can substitute caliper measurements for PP distance (LR, Y:O2, X:O3, -0.70 (-3.28-1.38), 0.98 (0.93 ± 1.04)), its validity for "A" distance is lower (LR, Y:O2, X:O3, -2.37 (-13.53-4.83), 1.02 (0.62-1.75)). Conclusions: US is a reliable and valid tool in identifying anatomical landmarks for diagnosing A2 pulley ruptures, particularly for detecting the midpoint of the proximal phalanx. This is important to differentiate between complete and partial A2 pulley tears. However, the measurement of the "A" distance requires further refinement. These findings support efforts to standardize US examination protocols and promote consensus in diagnostic methodology, though further research is needed to address the remaining challenges.