This paper examines the process and issues involved in the management of advertising risk by advertisers with a focus on the case of a leading UK financial company, Clerical Medical Investment Group. The idea of an advertising risk cycle is proposed given that managers are likely to adapt their risk-taking according to past successes or failures. The factors influencing the propensity of advertising risk-taking are analysed focusing on budgetary slack, media scheduling, stakeholder perspective, management practices, environment, campaign planning process and knowledge and experience. Clerical Medical's advertising experience since 1990 largely supports the hypotheses for the risk cycle and propensity to take advertising risks. It is recommended that advertisers utilise appropriate pretesting techniques along with effective and rigorous planning and advertising risk audits.