Covering your tracks out of fear of getting caught with your hands in the digital cookie jar can sometimes get you in more trouble than whatever crime the feds think you may have committed in the first place. This presentation identifies three specific scenarios where the act of trying to cover your digital footprints - oftentimes in innocuous and legal ways - can get you into trouble: the nebulous crime of “anticipatory obstruction of justice,” which can cover something as mundane as deleting an email before you’re even suspected of committing (let alone charged with) a crime; the ever-expanding Computer Fraud and Abuse Act, which has been stretched to cover things that are neither fraudulent nor abusive; and the potential problems with encryption. The presentation will conclude with some ways you can protect yourself that can help minimize claims that you obstructed justice.