This paper investigates the potential causes of the vulnerabilities of free content websites to address risks and maliciousness. Assembling more than 1,500 websites with free and premium content, we identify their content management system (CMS) and malicious attributes. We use frequency analysis at both the aggregate and per category of content (books, games, movies, music, and software), utilizing the unpatched vulnerabilities, total vulnerabilities, malicious count, and percentiles to uncover trends and affinities of usage and maliciousness of CMS{'s} and their contribution to those websites. Moreover, we find that, despite the significant number of custom code websites, the use of CMS{'s} is pervasive, with varying trends across types and categories. Finally, we find that even a small number of unpatched vulnerabilities in popular CMS{'s} could be a potential cause for significant maliciousness.