Self-stigma predicts treatment avoidance and disengagement among people who use drugs (PWUD), yet conversational systems aiming to provide support typically treat self-stigma expression as a uniform signal. We present a three-phase, proof-of-concept study of a persona-aware approach to LLM support. Latent Profile Analysis (LPA) on indicator-level features from 1,174 self-stigma expressors on Reddit yields a four-persona typology validated against held-out behavioral and linguistic features. Sequential Bayesian and recurrent neural classifiers recover these personas from limited posting histories, substantially outperforming batch and few-shot LLM baselines (macro-F1 = 0.74 at 30 posts). Evaluation by eight clinical experts across three contemporary LLMs revealed a misalignment: persona-matched responses successfully achieved targeted behavioral shifts, yet raters holistically preferred the generic empathy of the persona-neutral baseline. Our findings suggest that holistic empathy judgments and clinically-aligned response design can pull in opposite directions, and that evaluating LLM-based stigma support requires rubrics capable of decomposing the two.

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