Last year, Brett Burney (Nextpoint), Kelly Twigger (Minerva26), and Doug Austin (eDiscovery Today) unpacked the thorny issue of hyperlinked files in ediscovery. The conversation was so impactful that we brought the same expert panel back for part two – diving deeper into what’s changed, what’s new, and what still makes hyperlinked files such a challenge.
What Are Hyperlinked Files, Anyway?
Let’s start with the basics. Instead of the traditional method of attaching a Word document or PDF directly to an email (what Brett prefers to call “traditional email attachments” rather than the misleading term “physical attachments”), hyperlinked files involve sending links to documents stored in cloud platforms like OneDrive, Google Drive, or SharePoint.
You may be wondering, what’s the difference? Traditional attachments are encoded and embedded in the email itself. Hyperlinked files are just pointers to documents that live elsewhere – documents that can be edited in real-time by multiple collaborators. This shift has changed how we think about email “attachments” and their ediscovery obligations.
Brett notes:
I like to tell people we’ll focus on the intent of the sender — was this intended to be ‘attached’ or linked to in this email message?
The terminology has evolved too. The panel originally called this phenomenon “modern attachments” in the first webinar, but they’ve now settled on “hyperlinked files” as the preferred industry term, reflecting how the conversation has matured over the past year.
The Legal Reality: Courts Say You Must Produce Them
Courts have consistently ruled that hyperlinked files must be produced in discovery when they’re relevant and responsive. As Kelly noted, nearly 40 court decisions have addressed this issue since the panel’s first discussion, and the trend is clear.
Kelly says:
The only thing that’s changed is the difficulty in getting to the hyperlinked files technologically. So I don’t know that the ‘is it relevant or responsive’ argument is going to hold up as we move forward.
The legal reasoning is pretty straightforward: If a traditional email attachment would have been produced, then its hyperlinked equivalent should be too. The only thing that’s changed is the technology – and the difficulty of collecting these files. Courts aren’t letting technological challenges excuse discovery obligations. But as Kelly noted, these obligations could change as hyperlinked files become more technically difficult to obtain.
The Collection Nightmare
This is where things get messy. While Microsoft has made some progress with its cloud attachment collection feature in M365, the limitations are pretty significant:
- You need premium E5 licensing
- The retention policy must be enabled BEFORE the files are created
- It only captures files going forward, not historical data
- Google Workspace offers even fewer options for collecting the right versions
Because of this, many organizations discover they can’t collect the versions of documents that existed when emails were sent – only current versions that may have been edited multiple times since.
The Preservation Challenge
Doug highlighted a preservation nightmare that keeps many legal professionals awake at night. When you put a custodian’s mailbox on legal hold, you’re only preserving the files they send, not the files they receive from others. Those linked files live in other custodians’ repositories, forcing you to either cast a much wider preservation net or abandon in-place preservation altogether.
Consider this scenario: Sarah receives an email from a colleague with a link to a SharePoint document. If that colleague isn’t under legal hold, the document could be modified or deleted without Sarah having any control over it. The traditional custodian-based approach to preservation starts to break down.
The Proportionality Problem
Perhaps the most significant challenge is the burden shift that’s occurring. Courts are increasingly requiring parties to specify which hyperlinked files they want, rather than requiring producing parties to deliver everything automatically.
This creates an unprecedented burden on receiving parties who must:
- Sift through productions to identify which documents contain hyperlinks
- Determine which linked files are important enough to request
- Navigate complex processes to actually obtain those files
- Do all of this manually, often under tight court-imposed deadlines
As Kelly pointed out, some courts have established detailed protocols – like allowing 50 hyperlinked document requests per week. But these processes are time-consuming and resource-intensive.
The challenge isn’t limited to traditional email platforms. Hyperlinked files appear in Microsoft Teams, Slack, Salesforce chat functions, and virtually any communication platform that allows file sharing. The more collaborative tools organizations adopt, the more complex this issue becomes.
The speakers noted that we’re likely to see more cases extending beyond the typical Outlook-to-SharePoint or Gmail-to-Google Drive scenarios. Shadow IT applications and emerging communication platforms will only add to the complexity.
What “Contemporaneous” Really Means
What constitutes the “contemporaneous” version of a hyperlinked file? Is it the version that existed when the email was sent, or when the recipient first opened it? If someone is on vacation for two weeks and the document is modified several times before they return, which version matters?
The courts haven’t definitively answered this question, leaving room for interpretation and potential disputes.
Practical Steps Forward
Despite the challenges, the experts offered several actionable recommendations.
For organizations
- Understand your current technical capabilities before agreeing to any legal protocols
- Consider enabling Microsoft retention policies proactively, but understand the limitations
- Conduct regular testing of your collection capabilities across different platforms
- Build a team approach
For legal teams
- Draft case-specific protocols rather than recycling old templates
- Include proportionality arguments and modification clauses for technological limitations
- Understand what licenses and capabilities the opposing party has
- Plan for the manual burden of identifying and requesting hyperlinked files
For everyone
- Stay educated on rapidly evolving platform capabilities
- Follow experts like Mike McBride and Greg Buckles for Microsoft updates
- Understand that this technology changes faster than most can keep up with
★ Watch the Full Discussion
Want to dive deeper into the complexities of hyperlinked files? The complete webinar recordings for Parts 1 and 2 are available on-demand and includes detailed case law analysis, technical collection strategies, and practical protocol examples.
