What began as a trademark infringement dispute concerning electronic cigarettes has evolved into a never-ending series of discovery issues, and lessons about the limits of Federal Rule of Evidence 502 and privilege waivers. DR Distributors, LLC filed its initial complaint against 21 Century Smoking, Inc and its owner, Brent Duke, in September 2012 alleging trademark violations. The defendants filed their counterclaim also alleging trademark violations about a month later. Though fact discovery was supposed to have ended in 2015, the parties continued to assert problems with discovery seven years later. The latest issue presented before the U.S. District Court in the Northern District of Illinois in this case was whether the defendants waived the marital communications privilege by disclosing certain communications during discovery. In its decision finding that the privilege had been waived, the Court described the limited application of Rule 502 and warned against the dangers of arguing that a disclosure was “inadvertent” without providing any explanation of how the privilege review was performed.