In Alsayiri v. Crucial MRO, LLC, the defendants produced 169 pages of documents, with more than half being training certificates. The emails from the period around the plaintiff's March 2022 termination were missing. Counsel confirmed they had been deleted, partly due to an auto-deletion feature.
The court found that the defendants "failed to take reasonable steps to preserve the ESI." They avoided the harshest sanctions under Fed.R.Civ.P. 37(e)(2) only because the plaintiff couldn't prove intent to deprive. However, they faced a jury instruction about the lost ESI, a bar on using later-discovered emails, and a restriction on arguing that no discriminatory statements appeared in 2022.
Negligence is a lower bar to clear than bad faith, and many teams fail it for ordinary reasons.
Why These Mistakes Keep Happening
Preservation failures rarely come from malicious intent. They arise from gaps between functions. IT manages the email platform. Legal handles the Legal Hold. Records and Information Management oversees the Records Control Schedule. Nobody owns the seam where these three meet. Add a system migration or a departing employee, and defaults take over. Defaults delete.
Mistake 1: Starting the Duty to Preserve Too Late
Why it happens: Teams often treat the service of the complaint as the starting point. The Alsayiri defendants argued the duty began with the third amended complaint in September 2024, or at the earliest with the EEOC charge in May 2023. The plaintiff had been terminated in March 2022.
Consequence: The court rejected the timing argument, and the emails from the critical window were already irretrievably lost.
Fix: Define trigger events by reasonableness, not by service. Reasonable anticipation of litigation can arise from a termination of a protected-class employee, a demand letter, an internal complaint, or an agency charge. Write a short trigger matrix into your Legal Hold procedure and require a documented decision whenever one of those events occurs. Document the "no hold needed" decisions too.
Mistake 2: Leaving Auto-Deletion Running
Why it happens: Auto-deletion is usually configured once, years ago, to control storage and apply a Records Control Schedule. It runs quietly. Nobody connects it to a dispute that surfaces later.
Consequence: The court attributed some of the loss to "a negligent failure to suspend the system's auto-deletion features," including for departing employees.
Fix: Build suspension into the Legal Hold workflow, not into a separate IT ticket someone has to remember. Your hold notice should trigger a Records Freeze on named custodians' mailboxes and shared repositories. Test it: confirm that the deletion job actually skips frozen accounts. Treat departing-employee mailboxes as a standing risk. If your offboarding process deletes mailboxes on a timer, add a legal check before that timer fires.
Mistake 3: Ignoring Preservation During System Migrations
Why it happens: Migrations are scoped around functionality and cutover dates. Preservation is assumed to travel with the data, and it often doesn't.
Consequence: The court concluded that some emails "were lost due to a poorly thought-out system migration." That finding contributed to the negligence conclusion.
Fix: Add a records and legal sign-off gate to every migration plan. Before cutover, inventory what's under hold, confirm those items are in scope for migration, and verify Fixity on what arrives. Keep the source system available until verification is complete. Make the sign-off a named person's responsibility, not a committee's.
Mistake 4: Relying on Involved Employees to Preserve
Why it happens: It feels efficient. The people closest to the events know where the documents are. The Alsayiri defendants argued their attorneys were entitled to rely on the company owner and an employee to run ESI searches.
Consequence: The court called that "beside the point." The relevant question was whether anyone took reasonable steps to preserve, not whether searches were done afterward. The defendants pointed to no evidence that anyone tried to preserve emails on the servers for the key February to March 2022 period.
Fix: Separate preservation from collection and from search. Preservation is a system-level act, executed by IT or a vendor under counsel's direction, not left to custodians' discretion. Keep a written record of who did what, when, and on which systems. That record is your proof of reasonable steps.
Mistake 5: Assuming Negligence is Safe
Why it happens: Teams read Rule 37(e)(2) and its intent-to-deprive standard and conclude that, absent bad intent, they're protected. Intent is hard to prove, since it often rests on circumstantial evidence. The plaintiff here couldn't meet it.
Consequence: Rule 37(e)(1) still applies once the court finds prejudice. Prejudice doesn't require a smoking gun; the court said "some prejudice" is enough, and that a party need only offer plausible, concrete reasons the lost evidence mattered. Where the production is thin, as it was here, and the lost material is substantial, prejudice is easy to show. The sanctions still shaped how the defendants could try their case.
Fix: Stop treating the intent standard as your safety margin. Your goal isn't to avoid a finding of bad faith. It's to avoid any finding of unreasonable steps. Measure your program against the reasonableness question, because that's the one the court asked.
Prevention Checklist
- Maintain a written trigger matrix that ties Legal Hold decisions to events, not to service of process.
- Require a documented hold or no-hold decision at each trigger.
- Make auto-deletion suspension part of the Legal Hold workflow, with a verification step.
- Review departing-employee mailbox deletion timers against active matters.
- Add a legal and records sign-off gate to every system migration.
- Verify Fixity and scope of held data before decommissioning any source system.
- Assign preservation to IT or a vendor, not to custodians involved in the dispute.
- Log every preservation action with date, system, and responsible person.
- Audit hold effectiveness on a schedule, not only when litigation arrives.
- Align your Records Control Schedule with hold procedures so disposition stops when a hold begins.
The Alsayiri defendants didn't lose on intent. They lost on process. Fix the process before a dispute tests it.
