Systems and methods are disclosed permitting a sender to send a secret and secure message to a recipient. An application on a sender device interfaces with known message generating tools to permit a user to generate a message. The local application encrypts the message (and optional attachments) based on public/private key pairing negotiated with the server given the recipient device id. The sender device transmits the cipher text to the server. The server generates a benign, text-based, context-appropriate message and delivers same to a recipient device by way of a known messaging service. The benign message provides a secret clue to the recipient that an encrypted message is available. Recipient may then access and decrypt the encrypted message, such as from the server in response to a successful challenge (e.g., password request).