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We term this Conversational Risk Accumulation (CRA): gradual intent drift, fragmented assembly of prohibited instructions, and sensitivity build-up from repeated disclosures. We propose a session-layer CRA Framework that tracks three trajectory signals: semantic drift from a session anchor, a sensitivity-weighted information accumulation graph over extracted entities, and a compliance-gradient signal capturing increasing willingness to comply. For scoring, we provide (i) an unsupervised convex fusion for attribution and ablations, and (ii) CRA-Net DA, a compact learned trajectory model trained with family-adversarial objectives to reduce length and topic-coverage confounds. 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