A posthumous message delivery system provides an online means to leave messages after death. The system utilizes inspirations to help the user prepare messages for each of the individuals on their recipient list, and the user can select from a variety of messaging platforms in which the message will be sent, including e-mail systems and social media systems, and the system automatically incorporates the inspirations into a message or selects a completed message. At the time of the user's death, the messages are authorized for release by an appointed trustee using a pin or password. The messages may be immediately released at the time of authorization or the messages may be configured for release at various milestones. The user has the capability of adding, deleting, and editing messages. Messages can be sent to groups of recipients, including social media contacts, or the messages may be limited to selected recipients.