A system and methods allowing the creation, integration, and transaction of rule circumventions and/or interactive advertisements in computing environments is provided. In an illustrative implementation, the present invention comprises a core transaction server, a multimedia transaction server, and browser application. A computing environment cooperates with the core transaction server to obtain data representative of computing environment rule circumventions for integration within the computing environment as well as computing environment circumvention transaction information. The core transaction server cooperates with the multimedia transaction server to obtain data representative of the desired computing environment rule circumvention and with the browser application to obtain inputs from computing environment to establish accounts for use when transacting computing environment rule circumvention transactions.