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Blog  |  July 31, 2025

Taming Modern Data Challenges: Preservation Challenges and Best Practices for Linked Documents

In our last post, we discussed linked documents in terms of why the challenge exists, the dispute over what they should be called, and the historical collection challenges associated with them.

We continue our series on linked documents with a discussion of the historical preservation challenges associated with linked documents and best practices for addressing them in discovery.

Historical Preservation and Contextual Integrity Challenges

Many legal professionals talk about the challenge of collecting linked documents, but there are historical preservation challenges as well. Preserving linked documents may require ensuring that the content remains unchanged and accessible over time, but that can be difficult to impossible to accomplish:

Dynamic Content

Since linked documents can be modified after being linked to a communication, preserving the state of the document as it was at the time of the original communication can range from difficult to impossible. Some platforms don’t even retain multiple versions of documents, leaving only the current version available for collection. Depending on the extent of the modifications since the communication occurred, the current version may have reduced contextual integrity to the communication itself.

Metadata Association

It is important to maintain the relationship between an email (or other type of communication) and the linked documents it references, as this connection provides contextual information about the email and its associated content. However, preserving this contextual information can be difficult depending on the platform. Not all collection platforms maintain a link or embedded metadata that explicitly ties them back to the originating email.

In-Place Preservation Challenges

For platforms that provide in-place preservation capabilities with the ability to place a legal hold on custodial data, there can be gaps in that in-place preservation. M365’s E3/E5 license enables you to place a legal hold on a custodian’s various data locations (e.g., Mail, OneDrive, SharePoint, Teams, etc.), which may or may not include documents that were linked to a sent email. M365 currently does not automatically preserve linked documents by default. For example, a hold can be placed on a custodian’s email box, but not on a Group OneDrive location where a linked document resides.

Recent advancements in M365 now allow administrators to enable linked document preservation on their tenant.  In addition, a version of the document at the time the link was sent can also be retained. More to follow on this topic further in the series.

Best Practices for Discovery of Linked Documents

Discovery of linked documents is a two-way street, potentially equalizing both the benefits and burdens of the parties’ discovery efforts. Here are some best practices from both a requesting and producing party perspective:

Requesting Parties

  • Learn about your opponent’s ESI sources as early as possible: This helps you understand their capabilities for preserving and collecting data, which will inform your negotiation strategy. Knowing what they can and cannot do – such as whether their platforms allow full custodian data preservation – can guide realistic and informed requests.
  • Understand preservation challenges and discuss preservation strategy with your opponent: If there are known limitations in platforms like Microsoft Purview, raise those issues early and clarify how your opponent intends to preserve relevant data. Be sure to include these concerns in preservation letters, especially when sent before a case is filed.
  • Plan for increased non-party subpoenas to obtain linked documents: If the linked documents are outside your opponent’s possession, custody, or control, be ready to issue subpoenas promptly. Prepare to argue why those files are necessary – especially if a non-party moves to quash – by showing that the email alone is incomplete without the hyperlinked content.
  • Push for production of responsive ESI from non-email custodian data locations, even if not linked to messages: While producing linked documents may be burdensome, producing them independently should not be difficult. Request that your opponent search and produce responsive documents from relevant storage locations regardless of linking challenges.
  • Pick your battles and prioritize critical data: Some data may be unavailable, so focus on what matters most to your case. Request high-value data early and be prepared to demonstrate its importance when facing proportionality or burden objections. Articulate the benefit of the data in specific, concrete terms to outweigh the claimed burden.

Producing Parties

  • Understand your technological capabilities and limitations before agreeing to anything: As we’ll discuss in our next post, a party in one case agreed to produce linked documents in their ESI protocol before understanding their capabilities and limitations in doing so. Know your limits up front to avoid similar consequences.
  • Be proactive about addressing preservation challenges and vulnerabilities: Don’t ignore known limitations, such as those in Microsoft 365, because transparency can be your friend. Preservation is not the place to take an “it’s better to ask forgiveness than permission” approach. Be prepared to argue the reasonableness of your preservation efforts before any potential spoliation issues arise – courts may not be sympathetic if data is lost due to avoidable oversights.
  • Provide specific, well-supported burden arguments: Under FRCP Rule 34(b)(2)(B), objections must be stated with specificity. Generic objections like “overly broad” or “unduly burdensome” are considered boilerplate and may result in a waiver of those objections. To preserve your position, detail exactly why a request is burdensome or disproportionate.
  • Don’t rely on past case law to avoid producing linked documents: While some courts have ruled against requiring production of linked documents as modern attachments, those decisions were based on the technology available at the time. As technology improves, courts may expect more, so precedents may not protect you in future matters.
  • Maximize the use of technology you already have: You’re not necessarily obligated to upgrade to more expensive tools (e.g., moving from an M365 E3 to E5 license). However, if you already have advanced capabilities – like those available under an E5 license – you may be expected to use them. Courts are less likely to excuse non-production if you’re not fully leveraging available tools.

Conclusion

When it comes to discovery of linked documents, “the struggle is real” and it is often difficult or even impossible to produce the version of the document linked at the time of sending. It’s important to work with a provider that keeps current with the technical challenges and trends associated with linked documents to understand the discovery challenges they present and has identified solutions to address those challenges.

With that in mind, in our next post in the series, we will continue our discussion of linked documents with a discussion of technological developments and updated approaches that Cimplifi has identified for addressing linked files!

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

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