Technology

Stupid Lawyer Tricks: Legal Tech Edition

Learn from these lawyers' mistakes. Don't allow technology to get the best of you -- or your case.

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The legal profession seems to be in the midst of a perfect storm of technological ineptitude. Within the past few weeks, we have seen report upon report of major tech-related mess-ups by lawyers, resulting in some cases in inadvertent disclosures of privileged or confidential information and in another in the failure to timely file an appeal.

Let’s recap some of these recent horror stories.

The unintended email CC. Somewhere in the offices of Wilmer, Cutler, Pickering Hale and Dorr, a lawyer may now be suffering tremors every time he or she goes to press the email send button. Because somewhere in that firm is a lawyer who, when sending privileged documents describing whistleblower claims against Wilmer’s client PepsiCo to other lawyers working on the case, inadvertently copied a Wall Street Journal reporter.

In an article published Sept. 27, SEC Probes Departure of PepsiCo’s Former Top Lawyer, three WSJ reporters recounted that they came to learn of the secret SEC investigation when the information was “mistakenly sent by a WilmerHale attorney to a Wall Street Journal reporter as part of communication to other attorneys working on the matter.”

Later the same day, Wilmer issued an explanation and apology. According to Corporate Counsel, Wilmer’s statement said:

We deeply regret that privileged documents were inadvertently emailed to a reporter at The Wall Street Journal. WilmerHale takes full responsibility, and we apologize to our client. We promptly advised The Wall Street Journal of the error and asked the reporter to delete the material. The reporter told us he had deleted the material, but we later learned he had printed and retained hard copies.

We are disappointed that The Journal has decided to publish private information it knew was protected by our client’s legal privilege. We are taking additional measures designed to ensure that emails are not misaddressed to unintended recipients.

I would love to know what the “additional measures” are that Wilmer is taking to keep emails from being misaddressed. Perhaps they could package it and sell it to all the rest of us who also add inadvertent CC’s.

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The DOJ’s unredacted redaction. One of the oldest tricks in the book to test whether a document is properly redacted is to highlight the redacted portion, copy it, and paste it into another document. If you can read the supposedly redacted text, then you clearly have a problem. This can happen in a PDF document when the image layer is blacked out but the underlying text remains.

If anybody should know how to properly redact a document, you would think it would be the lawyers of the U.S. Department of Justice. But in an exclusive report by Law360, Exclusive: DOJ Redaction Flub May Undermine Libor Case, reporter Jody Godoy detailed how the DOJ’s failure to properly redact a document exposed secret testimony by a former Deutsche Bank trader, Gavin Black, that could taint the DOJ’s Libor-rigging case against him.

The redactions were made in a motion filed in U.S. District Court in New York by attorneys in the DOJ’s criminal division. Protecting the testimony was crucial to the DOJ’s prosecution, Godoy reported. But no one at the DOJ noticed the improper redactions until the Law360 reporter asked about them. The DOJ quickly replaced the document with one that was properly redacted, but the flubbed document was publicly available for more than 12 hours.

One sentence was highlighted in black and written in a gray font that was clearly legible. Other portions of the brief were blocked out with what appeared to be black highlighting but were easily read by copying and pasting the contents of the brief into another text document. Word searches of the document returned text that was barely hidden behind the faulty redactions.

A DOJ spokesperson attributed the improper redactions to “a technical error in the electronic redaction process” that allowed for “manipulation” of the file’s “metadata,” according to Law360.

Sponsored

That’s lawyer-speak for, “We messed up.”

Blame it on the spam filter. When a law firm misses a deadline for filing an appeal, fingers of blame are sure to start pointing. In the case of the Pensacola, Fla., law firm Odom & Barlow, they pointed straight at the firm’s email system spam filter.

The defendant in this eminent domain case had filed motions seeking reimbursement of legal fees of some $600,000, but the lawyers for the plaintiff never responded. After 14 months with no response, the judge ordered the plaintiff to pay those fees.

Problem was, the plaintiff’s law firm claimed it never received the motions or the judge’s order, because its email system was identifying the court’s emails as spam and automatically deleting them. But when the firm asked the judge to vacate and reenter his order so that it could file a timely appeal, the judge was not sympathetic, and neither was Florida’s District Court of Appeal.

The firm, against the recommendation of its IT consultant, had configured its email system to automatically delete spam without alerting the recipient. Even though the IT consultant warned this created a risk of deleting legitimate emails, the firm did not want to spend the extra money on a less-risky alternative.

[T]estimony was presented that the spam filter of Odom & Barlow’s server was deliberately configured in such a way that it could delete legitimate emails as spam without notifying the recipient, despite Odom & Barlow being warned against this configuration. … Based on this testimony, the trial court could conclude that Odom & Barlow made a conscious decision to use a defective email system without any safeguards or oversight in order to save money. Such a decision cannot constitute excusable neglect.

With the added cost of the appeal, the defendant’s attorneys’ fees are now estimated to be more than $1 million, according to the Pensacola News Journal.

Robert Ambrogi Bob AmbrogiRobert Ambrogi is a Massachusetts lawyer and journalist who has been covering legal technology and the web for more than 20 years, primarily through his blog LawSites.com. Former editor-in-chief of several legal newspapers, he is a fellow of the College of Law Practice Management and an inaugural Fastcase 50 honoree. He can be reached by email at ambrogi@gmail.com, and you can follow him on Twitter (@BobAmbrogi).

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