Abstract: Embodiments of the systems and methods disclosed herein enable automated and customized insertion of advertisements in real-time and in response to a request for a content file. Purveyors of content, such as audio and video, often use advertisements to ensure profitability. Embodiments enable users to customize the location(s) for advertisement insertion, and further embodiments allow for real-time insertion of ads, the ads can further be customized to the ad recipient. Real-time, automated delivery improves current technology in several ways by, for example, eliminating the need to manually inserting or choosing advertisements, customizing advertisement delivery to the content recipient, improving the speed of delivery of ad-supported content, giving users the ability to customize the location of advertisement insertion, thereby improving the final ad-supported product by inserting ads in logical, non-pre-planned locations of content files.