Most teams treat Microsoft 365 Copilot enablement as a licensing and pilot exercise. In mid-2026 that approach still fails first on the same two operational realities: years of overshared SharePoint and OneDrive content, and incomplete sensitivity labeling that leaves Copilot with almost no content-level guardrails. The single most underestimated friction is the labeling gap. Once Copilot is live it surfaces, summarizes, and synthesizes