While some prior studies of work-based assessment (WBA) numeric ratings have not shown gender differences, they have been unable to account for the true performance of the resident or explore narrative differences by gender. To explore gender differences in WBA ratings as well as narrative comments (when scripted performance was known). Secondary analysis of WBAs obtained from a randomized controlled trial of a longitudinal rater training intervention in 2018-2019. Participating faculty (n = 77) observed standardized resident-patient encounters and subsequently completed rater assessment forms (RAFs). Participating faculty in longitudinal rater training. Gender differences in mean entrustment ratings (4-point scale) were assessed with multivariable regression (adjusted for scripted performance, rater and resident demographics, and the interaction between study arm and time period [pre- versus post-intervention]). Using pre-specified natural language processing categories (masculine, feminine, agentic, and communal words), multivariable linear regression was used to determine associations of word use in the narrative comments with resident gender, race, and skill level, faculty demographics, and interaction between the study arm and the time period (pre- versus post-intervention). Across 1527 RAFs, there were significant differences in entrustment ratings between women and men standardized residents (2.29 versus 2.54, respectively, p < 0.001) after correction for resident skill level. As compared to men, feminine terms were more common for comments of what the resident did poorly among women residents (β 0.45, CI 0.12-0.78, p 0.01). This persisted despite adjusting for the faculty's entrustment ratings. There were no other significant linguistic differences by gender. Contrasting prior studies, we found entrustment rating differences in a simulated WBA which persisted after adjusting for the resident's scripted performance. There were also linguistic differences by gender after adjusting for entrustment ratings, with feminine terms being used more frequently in comments about women in some, but not all narrative comments.