A system and method for securely encrypting and booting a headless appliance. A method includes providing the headless appliance with content stored in a memory, wherein the content is encrypted with a key, and wherein the key is separately stored on a remote computing device; booting the headless appliance and loading a fallback configuration; in response to a user device connecting to the headless appliance, directing the user device to a captive portal and capturing credentials of a user; forwarding the credentials to the remote computing device for verification by an identity provider; in response to the credentials being verified as a non-administrator, granting access to a public network for the user; and in response to the credentials being verified as an administrator, obtaining the key from the remote computing device to decrypt the content to provide access to a private network for the user.