Disclosed is an automated insert feeding system and related methods, capable of removing bulk-packaged items from a tray or other package, and separating the bulk-packaged items individually for distribution into individual packages in high speed reliable fashion. The disclosed systems can also be loaded with multiple packages of the pre-packaged items for automatic feeding into the system which allows human operators to load several packages and allow the system to work unattended, thereby reducing man-hours spend on the process.