Systems and methods for managing privileged communications in a controlled-environment facility are disclosed. A privileged communication is received from a user via an online portal, wherein the user having been previously confirmed as having a privileged relationship with a resident of the controlled-environment facility, transmitting the privileged communication to the resident in a manner that prevents inspection by controlled-environment facility staff, and notifying the user when the privileged communication has been accessed by the resident. The privileged communication may be one or more of a document, an image, a text message, an email, a voicemail, or any other electronic or digital communication.