As another U.S. election cycle nears, compliance personnel at investment advisers need to ensure their firms’ employees only make authorized campaign contributions. Fortunately, compliance professionals have had a decade to become well versed in the federal pay to play requirements in Rule 206(4)‑5 under the Investment Advisers Act of 1940. State and local elections happening simultaneously around the country could, however, raise issues under the federal pay to play requirements, as well as under state and local rules, which are far less familiar to fund managers, more varied in their scope and often more stringent than the federal pay to play rules. To discuss risks under the pay to play rules and help ensure ongoing compliance, the Private Equity Law Report recently interviewed Katten partner David Y. Dickstein for his insights. In this article, Dickstein discusses the three primary prohibitions under the federal pay to play rules, with thorough analysis of the requirements of the two-year timeout prohibition; suggests unique issues introduced by the coronavirus pandemic and potential SEC activity in the area; and identifies concrete steps compliance professionals can take to protect their firms. For additional insights from Dickstein, see our two-part series on marketing to public pension plans: “Municipal Advisors; Pay to Play Laws; and Gift and Entertainment Rules” (May 28, 2019); and “Honest Services Fraud, Use of Placement Agents and Lobbyist Registration Issues” (Jun. 4, 2019).