Systems, devices and methods for the assessment and mitigation of risk associated with the potential loss of data stored by an IHS (Information Handling System). The risk assessment incorporates contextual and behavioral data provided by the IHS where the data describes file operations by the IHS, the physical use of the IHS, system information that describes the platform of the IHS and hardware installed on the IHS and data backup procedures implemented by the IHS. Based on the data associated with an IHS, a scoring algorithm determines a behavioral risk of loss that reflects the use of the IHS and a contextual risk of loss that reflects user input to individual files, thus indicating the time required to recreate a file. The backup procedures implemented by the IHS are then evaluated in light of the determined risk assessment. Backup procedure recommendations that mitigate the identified risks are provided to the IHS.