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Cached insight blobs persisted before B5c shipped don't carry the new `rationale` field — the strict parser would reject them, and auto-regenerating on every cache-hit would burn rate-limit tokens silently. Instead the route now detects the legacy shape and surfaces a `legacyPayload: true` flag in the response so the UI can render a one-time "regenerate for new explainability features" CTA. User-initiated regeneration stays the trigger. `isLegacyInsightPayload(payload)` lives in `src/lib/ai/legacy-payload.ts` and is intentionally lenient: any rec missing rationale (or the v1.4.14/v1.4.15 string-only InsightResult shape) flags. Empty recommendations[] is NOT legacy — it's a legitimate refusal payload. The annotate() Wide-Event also carries `legacyPayload` on cached hits so the admin AI quality dashboard can chart the migration ratio over time. v1.4.17 can flip auto-eviction on once the ratio drops near zero. 7 new tests in `legacy-payload-detection.test.ts` pin the contract. Existing 223 AI tests still green; typecheck clean. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>