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In-house counsel play dual roles of business person and attorney, often at the same time. One of the challenges during litigation is to parse out those roles in order to protect the attorney-client privilege. A recent case in the Southern District of New York highlights the dangers of that process. It also demonstrates how inadvertent production of privileged documents may occur and the importance of asserting attorney-client privilege as soon as possible after such production. In Jacob v. Duane Reade, Inc., assistant store managers at Duane Reade brought a collective action suit for overtime wages under the Fair Labor Standards Act (FLSA). Before the court was a motion by Duane Reade for an order declaring that an email accidentally produced in discovery was protected by attorney-client privilege. The email at issue reported on a meeting that aimed to redraft store managers’ job descriptions and create strategies to ensure the managers met those descriptions, so that they would be exempt from coverage by the FLSA. The email contained descriptions of communications that Duane Reade’s in-house counsel made at the meeting.