Contextual StereoSet: Stress-Testing Bias Alignment Robustness in Large Language Models

Abstract: A model that avoids stereotypes in a lab benchmark may not avoid them in deployment. We show that measured bias shifts dramatically when prompts mention different places, times, or audiences -- no adversarial prompting required. We introduce Contextual StereoSet, a benchmark that holds stereotype content fixed while systematically varying contextual framing. Testing 13 models across two protocols, we find striking patterns: anchoring to 1990 (vs. 2030) raises stereotype selection in all models tested on this contrast (p<0.05); gossip framing raises it in 5 of 6 full-grid models; out-group observer framing shifts it by up to 13 percentage points. These effects replicate in hiring, lending, and help-seeking vignettes. We propose Context Sensitivity Fingerprints (CSF): a compact profile of per-dimension dispersion and paired contrasts with bootstrap CIs and FDR correction. Two evaluation tracks support different use cases -- a 360-context diagnostic grid for deep analysis and a budgeted protocol covering 4,229 items for production screening. The implication is methodological: bias scores from fixed-condition tests may not generalize.This is not a claim about ground-truth bias rates; it is a stress test of evaluation robustness. CSF forces evaluators to ask, "Under what conditions does bias appear?" rather than "Is this model biased?" We release our benchmark, code, and results.