Aims: Glenoid bone loss is a significant problem in the management of shoulder instability. The threshold at which the bone loss is considered “critical” requiring bony reconstruction has steadily dropped and is now approximately 15%. This necessitates accurate measurement in order that the correct operation is performed. CT scanning is the most commonly used modality and there are a number of techniques described to measure the bone loss however few have been validated. The aim of this study was to assess the accuracy of the most commonly used techniques for measuring glenoid bone loss on CT. Methods: Anatomically accurate models with known glenoid diameter and degree of bone loss were used to determine the mathematical and statistical accuracy of six of the most commonly described techniques (relative diameter, linear ipsilateral circle of best fit (COBF), linear contralateral COBF, Pico, Sugaya, and circle line methods). The models were prepared at 13.8%, 17.6%, and 22.9% bone loss. Sequential CT scans were taken and randomized. Blinded reviewers made repeated measurements using the different techniques with a threshold for theoretical bone grafting set at 15%. Results: At 13.8%, only the Pico technique measured under the threshold. At 17.6% and 22.9% bone loss all techniques measured above the threshold. The Pico technique was 97.1% accurate, but had a high false-negative rate and poor sensitivity underestimating the need for grafting. The Sugaya technique had 100% specificity but 25% of the measurements were incorrectly above the threshold. A contralateral COBF underestimates the area by 16% and the diameter by 5 to 7%. Conclusion: No one method stands out as being truly accurate and clinicians need to be aware of the limitations of their chosen technique. They are not interchangeable, and caution must be used when reading the literature as comparisons are not reliable. Cite this article: Bone Jt Open 2023;4(7):478–489.