Taming Modern Data Challenges: The Cimplifi Approach to Microsoft 365 Linked Documents for Relativity

In the two previous posts, we explored the reasons collecting and preserving linked documents are such a discovery headache as well as best practices for both requesting parties and producing parties in addressing them.

Now, we turn to the practical matter of how to handle these documents once they enter the eDiscovery pipeline: particularly when processing Microsoft 365 linked documents for loading into Relativity. In our experience so far, 80 to 90 percent of the linked documents we’ve seen have come from M365 and Google Workspace – with probably 20 percent of that from Google Workspace (as discussed in our post last year).

With M365 being the predominant source of linked documents to date, Cimplifi has developed pragmatic strategies through tailored workflows and custom scripting for bridging the gap between Microsoft 365’s evolving architecture and the demands of defensible discovery. In this post, we will discuss the Cimplifi approach to Microsoft 365 linked documents for loading into Relativity (both Relativity One and Relativity Server).

The Problem with “Perfect” Linkage

Whether they come from OneDrive, SharePoint, or Microsoft Teams, linked documents are inherently messy from a technical standpoint. The linkage between a message (like an email or chat message) and a document depends on platform access, retention policies, and user permissions. Often, even with access, metadata inconsistencies or deduplication challenges during processing can make it impossible to link a document back to its originating message with 100% certainty. That ambiguity is why Cimplifi recommends collecting or linking these documents only after evaluating platform capabilities and legal requirements.

Prioritizing Collection Workflows

Cimplifi applies a tiered approach to Microsoft 365 linked document workflows, depending on the client’s platform access and the case’s defensibility requirements. The process generally follows three escalating options:

• Option 1 – Relativity Collect with Auto-Injection: The ideal path is using Relativity Collect, which attempts to automatically collect and inject linked documents as part of the communication family. This approach provides the most streamlined experience for Relativity users. However, this method does have limitations: it can only collect the most recent version of a document and cannot access deleted documents preserved solely in the backend by Microsoft Purview.
• Option 2 – Purview-Based Collection Without Injection: If the use of Relativity Collect is not feasible or does not return sufficient results, Cimplifi can turn to Microsoft Purview’s platform directly to collect linked documents. These documents are then loaded into the workspace independently, which makes them searchable and reviewable, but not automatically linked to their source communications.
• Option 3 – Cimplifi Custom Linking Workflow: When linkages must be preserved or reconstructed, Cimplifi uses a proprietary script to correlate messages and attachments based on metadata such as Message ID, data source, and custodian. This “best effort” approach uses imperfect Microsoft metadata and advanced logic to approximate linkage in cases where direct association is otherwise unachievable. Cimplifi currently supports Teams and email using Purview V1, soon to be removed by Microsoft.  Purview V2 currently only allows for Teams linkage, given a more limited set of metadata provided by Microsoft.

Legal Holds, Retention Labels, and Reality Checks

One of the most important gating questions for linked document handling is whether a legal hold was in place at the time of communication. Microsoft 365 provides options to set retention labels that can preserve a snapshot of a cloud document as it was when shared. But unless these were properly configured in advance and an organization maintains an E5 license with Microsoft Purview, those versions may be irretrievable. This means that, for many organizations, linked documents may no longer be accessible, or may not reflect the state of the document at the time of the original message. Advance planning is key to success here.

Cimplifi makes it standard practice to ask about the presence of legal holds early in any matter. If the client hasn’t implemented certain retention or preservation policies before linked documents were shared, re-collection efforts may be futile. Understanding these risks up front can help clients avoid wasted effort and manage defensibility expectations.

Getting Technical: The Linking Script in Action

Cimplifi uses a specialized approach to intelligently restore connections between communications and their associated cloud attachments. This process relies on structured metadata, centralized access to source files, and quality assurance checkpoints to ensure accuracy and traceability.

For best results, Cimplifi recommends managing the full forensic collection process. Self-collected data may introduce inconsistencies that complicate linkage and require additional validation. Our method minimizes redundancy and enhances precision—especially within platforms like Relativity—by applying layered logic to match documents with their parent messages.

Metadata Updates for Relativity

Once documents are linked, metadata fields are updated in both the parent communication and the attachment itself to reflect the new family relationships. These updates allow review teams to navigate linked families just like they would traditional attachments – restoring a sense of context that might otherwise be lost.

Conclusion

Discovery of Microsoft 365 linked documents is not a “one-size-fits-all” proposition. Legal teams must weigh burden, proportionality, and technical feasibility in each case. However, through our detailed understanding of Microsoft’s evolving infrastructure and our ability to adapt collection and linking methods to the tools and licenses available, we can provide a structured, defensible way for our clients to address one of today’s most challenging eDiscovery issues. The technology is continually changing, which means using a provider like Cimplifi to keep up with those changes to automate the process – to the extent possible – is more important than ever.

In our next post in the series, we will conclude our discussion of linked documents with a discussion of key case law rulings associated with them!

For more regarding Cimplifi forensics & collections capabilities, click here.