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extract_outline appended the {truncated: True} sentinel as soon as len(outline) >= MAX_OUTLINE_ENTRIES, i.e. right after the 50th heading, before knowing whether a 51st exists. A document with exactly 50 headings was therefore reported as truncated, and uploads_middleware injected a misleading 'showing first 50 headings' hint into the agent's context. Use a lookahead: only mark truncated once a heading beyond the limit is actually seen, then drop that extra entry. Adds an exact-boundary regression test.