Navigating Modern eDiscovery Challenges: Hyperlinked Files, Mobile Devices, and Sanctions – Oh My!

The rapid evolution of technology has brought transformative changes to how we manage ediscovery. With the rise of collaboration tools, the ubiquity of mobile devices, and the ever-growing demands for electronic evidence, litigators are facing new, complex challenges. During my recent presentations for the Boulder County Bar Association and the Milwaukee Bar Association, we tackled some of the most critical issues on the ediscovery horizon in 2024, including hyperlinked files, the complexities of preserving mobile data, and the evolution of sanctions under Rule 37. Here’s a recap of what we covered, along with practical takeaways to help you navigate these tricky waters.

Hyperlinked Files: The New “Modern Attachments”

Hyperlinked files have fundamentally changed the game in ediscovery. Gone are the days of simple email attachments; now, we’re dealing with links to documents stored in the cloud via tools like Microsoft Teams or Google Drive. These “modern attachments” pose unique challenges for collection and preservation—and the courts are still catching up.

Key Issues and Tips

• What Do We Call Them? Hyperlinked files are not the same as traditional attachments, and courts have rejected the term “hyperlinks” to describe them. In my view, the most accurate term is “hyperlinked files,” as it highlights their evidentiary nature when linked to a communication.
• Proportionality Questions: When collecting hyperlinked files, the burden and cost often clash with the value of the evidence. Courts are increasingly considering proportionality under Rule 26(b)(1), so it’s critical to assess whether the effort to retrieve these files aligns with their importance to your case.
• Policies and Tools: If your client uses Microsoft 365, for example, implementing a cloud attachment policy is non-negotiable. This allows for the preservation of every version of a hyperlinked file. Without it, you’ll only collect the most recent version—which might not be the one relevant to your case.

Takeaway: Get ahead of these issues by including hyperlinked files in your ESI protocol. Understanding the technology your client uses and negotiating terms up front can save time, money, and headaches later.

Mobile Devices and Sanctions: The New Battleground

Mobile devices have become essential communication tools for businesses and individuals alike, which means text messages are now a goldmine for evidence. Yet too often, these messages are lost, deleted, or overlooked entirely, leaving parties vulnerable to sanctions under Rule 37(e).

Key Case Law Lessons

1. Miramontes v. Peraton: In this case, the court found that an employer may have control over employees’ personal devices if the employer knows they are used for business purposes. Failure to preserve text messages led to sanctions in the form of denying Peraton’s motion for summary judgment—a game-changer in employment litigation.
2. Skanska USA v. Bagelheads: Repeated oversights in collecting mobile devices led the court to find intent to deprive, issuing adverse inference instructions. This case shows that negligence can rise to the level of bad faith when it becomes a pattern.
3. Hunter’s Capital v. City of Seattle: The court found intent to deprive after multiple city officials—including the mayor—lost critical text messages. However, the sanction was limited to an adverse inference instruction, demonstrating the courts’ reluctance to impose harsher penalties even in the face of clear preservation failures.

Practical Tips

• Early Preservation is Key: Don’t rely on custodians to understand their preservation obligations. Take proactive steps to collect data early, especially from mobile devices.
• Audit Device Settings: On iPhones, for example, default text message retention is set to “forever.” If this setting is changed, the timestamp is logged. Use forensic analysis to uncover when changes were made and why—it could make the difference between proving negligence or intent.
• Leverage Technology: Tools like Microsoft Purview and forensic email collectors can streamline the collection of data from mobile devices and cloud platforms.

Takeaway: Timing and thoroughness are everything. Courts are increasingly scrutinizing patterns of inaction, and even unintentional losses can result in sanctions that derail your case.

Moving Forward: Practical Advice for Litigators

The most effective way to manage these ediscovery challenges is to take a proactive, informed approach. Here are my key recommendations:

1. Identify Data Sources Early: Talk with your client early and often about how they create, store, and communicate information. Don’t wait until discovery deadlines loom.
2. Create a Detailed ESI Protocol: Address hyperlinked files, collaboration tools, and mobile device data explicitly in your agreements. Include language that allows for modifications if proportionality becomes an issue.
3. Invest in Education: ediscovery is a constantly moving target. Take advantage of resources like the annual eDiscovery Case Law Report, attend events like the University of Florida eDiscovery Conference, and stay informed through podcasts like Case of the Week.

Final Thoughts

As litigators, our jobs are evolving. Beyond mastering litigation strategy and case-specific subject matter, we now must also understand the intricacies of ediscovery. It’s no small feat to keep up with the pace of technological and legal change, but the cost of falling behind is far greater.

If you’re feeling overwhelmed, start small. Identify the biggest risks in your cases—whether that’s hyperlinked files, mobile device data, or something else—and take steps to address them head-on. And remember, you’re not alone. Tools like eDiscovery Assistant exist to make your work easier, and I’m always happy to help guide you through these challenges.

Litigation is complex, but with the right approach, you can turn the complexity of ediscovery into a strategic advantage. Let’s embrace these changes and stay ahead of the curve—together.