A system and method for securely encrypting and booting a headless appliance. A computerized method is disclosed that includes: providing the network appliance with content encrypted with a secret key; launching the network appliance in a fallback configuration that provides limited operational capabilities; forwarding a request for the secret key to an online service that independently utilizes an identity provider to establish trust with an appliance administrator; receiving the secret key from the online service upon establishment of trust with the appliance administrator; decrypting the content with the secret key received from the online service; and utilizing the content to launch the network appliance in a full configuration.