Server-side insertion of digital content can be performed on a live streaming network. In one aspect, a server-side system and method for real-time digital content insertion can retrieve and insert custom digital content for each viewer or set of viewers based on criteria like viewer's location and or personal data. In one aspect, a server-side system and method allows for quick and seamless establishment of second screen experiences using invisible data embedded in the video streams with the ability to insert different digital content for each viewer. In one aspect, a system and method detects static areas in a video stream suitable for digital content insertion.