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We recently ran an experiment comparing real M&A due diligence documents (technical overviews, security controls, retention policies, and integration requirements) to see what inconsistencies and gaps surfaced automatically.

What stood out wasn’t missing documentation, but conflicting statements across documents that would normally pass a manual review. Things like architecture drift, unclear retention timelines, and control enforcement gaps that create post-close risk.

This write-up walks through a real diligence-style example, the kinds of issues that surfaced, and where automated comparison helped (and where human judgment still mattered).

Curious how others approach diligence at scale and whether automation has helped or hurt your process.