A system and related methods for providing greater security and control over access to classified files and documents and other forms of sensitive information based upon a multi-user, multi-modality permission strategy centering on organizational structure, thereby making authentication strategy unpredictable so to significantly reduce the risk of exploitation. Based on the sensitivity or classification of the information being requested by a user, approvers are selected dynamically based on the work environment, e.g., mobility, use of the computing device seeking access, authentication factors under applicable environmental settings, access policy, and the like.