Systems and methods for analyzing documentation for assessing potential fraudulent user submissions are provided. According to certain aspects, a server computer may receive an initial set of documentation descriptive of damage to a property asset, and may analyze the initial set of documentation to determine whether additional documentation is needed. The server computer may initiate a communication channel with a user device via which the additional documentation may be submitted, and the server computer may similarly analyze the additional documentation to determine a likelihood of fraud. The server computer may process the user submission accordingly.