Purpose Clinical problems of the upper extremity are common and cause significant disability. In spite of this, there is very little published literature with utility measurement in patients with upper extremity pathology or injury. Most of these problems will have utilities close to 1.0 which may present difficulties with utility measurement. We present our overall experience measuring utilities in upper extremity problems. Methods We measured the utility using the Visual Analogue Scale (VAS) and a variety of forms of the Standard Gamble (SG) in surrogates and patients with upper extremity problems including Carpal Tunnel Syndrome (CTS), basal joint arthritis, and fracture of the distal radius. We have measured the relationship of disease severity to utility by comparing scores with health status measures such as the carpal tunnel disease specific instrument and the Disabilities of the Arm Shoulder and Hand (DASH) where appropriate. Results Using the SG, we found the utilities associated with upper extremity pathology to lie between 0.9 and 1.0 on a scale of 0 to 1. For example, the average utility of CTS was found to be 0.97 and the most severe form of median nerve dysfunction 0.93. The VAS consistently yielded lower utility ratings than the SG. Patients most often provided higher utility ratings than surrogates. While the SG and VAS utilities both correlated with symptom severity measures in CTS patients, only the VAS correlated with a disability score in basal joint arthritis patients. Most patients who had experienced a distal radius fracture were not willing to gamble, providing utility estimates of 1.0 with the SG, but .808 with the VAS. The chained version of the paper SG was found to be a useful method to expand the upper end of the utility scale to discriminate within a pathologic entity. Conclusion Through our experiences at measuring utility close to 1.0 we recommend the chained version of the paper form of the SG as an efficient method to perform these measurements in conjunction with the VAS in a clinical population or in surrogates. Our results and experience will help the clinical researcher to embark on utility measurement for conditions with utilities close to 1.0 and are directly applicable to decision analysis and economic analysis for upper extremity pathology.