AI systems may miss indirect, culturally situated distress or provide support mismatched to the application context. Existing benchmarks do not jointly address cultural variation, application context, and practitioner disagreement. We introduce VEILED-SH, a benchmark and construction methodology for evaluating single-turn responses to indirect expressions of suicide, self-harm, and distress. Its 10,003 prompts span counselor chat, forum posts, platform search, and triage, drawing on Singapore-grounded sources and public datasets. An expert-validated multi-label taxonomy distinguishes intent, communicative function, and response behavior. Six automated profiles, individually calibrated to three peer-support practitioners and three clinicians, retain separate reference policies for proxy-alignment scoring. Evaluating five systems on a coverage-enriched sample reveals variation in proxy alignment across profile-generated reference policies, even for the same system responses.

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