With the approach of the midterm elections, the current political climate has spurred increasing levels of political involvement, including large numbers of political contributions. Although citizen participation in the electoral process is a laudable democratic ideal, donations by designated individuals to certain government officials can create issues for investment advisers that provide investment services to government entities such as public pension funds under Rule 206(4)-5 of the Investment Advisers Act of 1940 – the so-called “pay to play rule” (Rule). The Rule bars an investment adviser from collecting compensation for providing investment advice to government entities for two years after a covered employee makes more than a de minimis contribution to the campaign of an official who can influence the selection of investment advisers by those entities. The SEC recently released settlement orders for three separate proceedings against investment advisers for violating the Rule by continuing to provide investment advice for compensation to public pension funds or plans during the “timeout” period. These enforcement actions are a sign that the agency continues to target pay to play violations – even those involving relatively small contributions. See “Pay to Play, Revenue Sharing and Wrap Fees Remain on the SEC’s Radar” (Apr. 20, 2017); and “SEC Starts Year With Pay to Play Penalties” (Jan. 28, 2016). This article analyzes the Rule, discusses the relevant facts of these enforcement actions and presents insight from a compliance expert on their key takeaways. See “Four Pay to Play Traps for Hedge Fund Managers, and How to Avoid Them” (Feb. 5, 2015).