Systems and methods provide for an automated system for analyzing damage to insured property. An enhanced claims processing server may analyze damage associated with the insured item using photos/video transmitted to the server from a mobile device for analysis at the server in real time. Depending on network conditions, the mobile device may transfer images to the server in high definition or low definition. The server may send notifications to the mobile device to remind a user of the mobile device to capture and transfer images to the server. The server may analyze images to provide feedback to the insured user (e.g., insurance estimates).