Some of the world's most well-known IT companies are in fact advertising companies deriving their primary revenues through digital advertising. For this reason, these IT giants are able to continually drive the evolutions of information technology in ways that serve to enhance our everyday lives. The benefits of this relationship include free web browsers with powerful search engines and mobile applications. Still it turns out that free comes at a cost that is paid through our interactions within a digital advertising ecosystem. Digital advertising is not without its challenges. Issues originate from the complex platforms utilized to support advertising over web and mobile application interfaces. This is especially true for advertising links. Additionally, as new methods for advertising develop so too does the potential for impacting its underlying ecosystem for good or ill.