Why Microsoft 365 Breaks Traditional eDiscovery Assumptions

Many eDiscovery challenges blamed on Microsoft 365 are not caused by complexity or scale. They are caused by misaligned assumptions.

Traditional eDiscovery assumes that files are the unit of evidence, that ownership implies relevance, that permissions imply access, and that versions are interchangeable. Microsoft 365 and other collaboration platforms violate all of these assumptions by design.

Are Files Still the True Unit of Work in Microsoft 365?

Files are no longer the true unit of work in Microsoft 365. Work happens through hyperlinks instead of attachments, co-authoring instead of check-in/check-out, shared repositories instead of personal storage, and continuous revision instead of discrete drafts. Because work no longer produces self-contained files, a preserved file rarely tells the full story.

The evidentiary value lies not in the file itself but in which version existed at a specific moment, who accessed it, how it was shared, and what it was relied upon to do. Without that context, the file is incomplete.

Do Hyperlinks Create Hidden Preservation Gaps?

Hyperlinks create hidden preservation gaps because emails or Teams messages that contain a hyperlink do not preserve the document behind that link. This is not a configuration issue. It is simply how the platform works.

If the linked document lives in another user’s OneDrive, resides in a SharePoint site outside the custodian’s ownership, or has changed since the link was shared, then traditional custodian-based preservation silently misses the evidence that actually mattered. That is a structural gap, not an operational mistake.

Even when preserving groups or teams, modern knowledge workers often collaborate on cross-functional teams, creating gaps beyond departmental boundaries.

Do Permissions Prove What Actually Happened?

Permissions do not prove what actually happened, because they show potential access, not real behavior. Access is time-bound, revocable, and contextual. A user may have had edit rights to a SharePoint site for six months, but that tells you nothing about whether they ever opened a specific document, when they opened it, or what version they saw when they did.

Behavior, who actually viewed, edited, shared, or relied on content, is the evidentiary signal that matters. When discovery relies on inferred access instead of observed behavior, it replaces evidence with an assumption.

How Does Identity Change Over Time Affect Discovery?

Identity change over time affects discovery, because roles and responsibilities evolve while legal questions focus on the past. People change roles, teams, reporting lines, and responsibilities, but discovery requests are drafted around historical periods, not present-day org charts. Microsoft 365 reflects the present. Without effective-dated identity preserved and observable over time, discovery quietly substitutes who someone is now for who they were then. That substitution is rarely defensible.

Why Is Waiting to Address These Gaps So Risky?

Waiting to address these gaps is risky because critical context disappears quickly. Many organizations believe they can address these issues when a matter arises. By then, audit logs may be gone, versions overwritten, roles changed, repositories repurposed, and context irretrievable. The window for preservation doesn’t stay open while you decide whether it matters.

Microsoft 365 did not create this risk. It exposed it.

What Does Context-Aware eDiscovery™ Do Differently?

Context-Aware eDiscovery™ treats Microsoft 365 not as a data source to be flattened, but as an activity system to be preserved. By capturing identity over time, observed behavior, and document state and relationships as reconstruction-grade evidence, discovery reflects what actually happened inside collaborative systems, not what appears to exist today.

How Do You Close the Context Gap in Practice?

Traditional eDiscovery fails in Microsoft 365, not because it is underpowered, but because it is misaligned with how evidence is created. Context-Aware eDiscovery™ exists because that misalignment is now impossible to ignore.

The next post moves from doctrine to practice, and what this looks like when a legal team closes the context gap in a real matter.

This article is part of Cloudficient’s Context-Aware eDiscovery™ series leading up to Legalweek.