Techniques for inserting advertising content into digital content are disclosed. The system may determine a compatibility between advertising content and digital content, determine candidate advertising content and candidate digital content using the determined compatibility, determine that the candidate digital content includes an advertising zone specifying an area where advertising content may be inserted, determine that an advertising slot of the candidate advertising content matches the advertising zone, and select digital content from the candidate digital content. The system may further select advertising content from the candidate advertising content, and combine selected digital content and selected advertising content by inserting the selected advertising content into the advertising zone.