Research designed to increase our understanding of behavioral responses to chronic pain resulting from work-related cumulative trauma disorders (CTD) has been limited. This pilot study's main purpose was to examine the test-retest reliability of self-determined work and power during maximum and submaximum efforts in the performance of wrist flexion and extension movements of the CTD-affected extremity, using the LIDO WorkSET Simulator System. Data were collected from 22 subjects (11 men, 11 women) with chronic upper-extremity CTD, in two same-day sessions. Subjective reports of current pain in the CTD subjects were measured using a Visual Analogue Scale (VAS) and a Numerical Rating Scale (NRS). Upper-extremity work and power data were also collected on 12 healthy subjects as a control (6 men, 6 women). Pilot results included: acceptable test-retest reliability of the work and power measures in the CTD subjects; the CTD group demonstrated markedly lower (20% to 58%) maximum work, submaximum work, and maximum power values compared with the healthy group; gender variation was seen in the CTD and healthy groups with respect to work and power data, and women with CTD tended to report higher pain intensity than male cohorts. These results provide insight for future studies.