Abstract—Actors engaged in election disinformation are using online advertising platforms to spread political messages. In response to this threat, online advertising networks have started making political advertising on their platforms more transparent in order to enable third parties to detect malicious advertisers. We present a set of methodologies and perform a security analysis of Facebook’s U.S. Ad Library, which is their political advertising transparency product. Unfortunately, we find that there are several weaknesses that enable a malicious advertiser to avoid accurate disclosure of their political ads. We also propose a clustering-based method to detect advertisers engaged in undeclared coordinated activity. Our clustering method iden- tified 16 clusters of likely inauthentic communities that spent a total of over four million dollars on political advertising. This supports the idea that transparency could be a promising tool for combating disinformation. Finally, based on our findings, we make recommendations for improving the security of advertising transparency on Facebook and other platforms.