The rules on political contributions by investment advisers and their associates to elected officials who make decisions for government entities on advisory services are strict. Neither investment advisers nor certain employees may provide compensated advisory services within two years of a contribution, as per Rule 206(4)‑5 under the Investment Advisers Act of 1940, often called the Pay to Play Rule. No quid pro quo or actual intent to influence an elected official is required to run afoul of this rule. Moreover, the Pay to Play Rule applies to contributions made by designated employees while they are employed by the adviser, as well as to certain pre-employment contributions. An SEC enforcement action against an investment adviser serves as a cautionary tale in this election year that advisers should not forget that pre-employment political contributions may trigger the restrictions of the Pay to Play Rule. This article summarizes the cease-and-desist order entered by the SEC against the adviser on August 19, 2024. See “In an Election Year, Advisers Should Be Particularly Alert for Potential Pay to Play Issues” (Aug. 1, 2024); and “Fund Managers Must Continue to Guard Against Pay to Play Violations” (Oct. 29, 2020).