The Add-In That Failed
In March 2024, a Chicago law firm was managing discovery production in a contract dispute worth $12 million.
They had 2,000 documents to produce.
Instead of manually reviewing each document, they used a popular Word add-in for redaction automation that claimed to "automatically identify and redact privilege and confidentiality designations."
The add-in worked by scanning documents for keywords like:
- "Confidential"
- "Attorney-client"
- "Work product"
- "Privileged"
If it found these keywords, it would highlight the paragraph and mark it as "redacted."
But the tool had a critical flaw: it didn't actually delete the text. It just changed the text color to white (invisible on screen) while leaving the underlying text intact.
When the documents were converted to PDF for production, the white text became visible again.
The opposing counsel immediately spotted the error: 340 attorney-client communications were now visible, including privileged settlement discussions and legal strategy.
The law firm faced $80,000 in sanctions and a separate malpractice claim from their client.