This chapter evaluates the ad message strategies and creative executions of two major UK parties—the Conservatives and Labour. To what extent did the advertising connect with the overarching election marketing strategies employed by the parties? To what degree did the advertising engage the electorate to address their hopes and fears, thereby building their trust? To answer these questions, this examination utilises critical analysis of multisource evidence including research studies, documentary evidence, expert conference speakers, discussions, follow-up questions and commentary on social media. The chapter identifies good and bad practices and the strategic role advertising plays in the marketing of elections.