Embodiments of the invention are directed to a system, method, or computer program product structured for continuous authentication and encryption. In some embodiments, the system is structured for receiving content from an entity system, displaying the content as masked content, and determining, using cognitive analysis, that a user wearing smart glasses is viewing a first portion of the masked content through the smart glasses, where the first portion of the masked content is associated with a first content hash. The system is also structured for identifying a first decryption key associated with the first content hash and determining a first cognitive hash. The system is also structured for receiving a first wearable hash from the smart glasses, comparing the first cognitive hash to the first wearable hash, and in response to the first cognitive hash matching the first wearable hash, transmitting the first decryption key to the smart glasses.