A document delivery system for electronic and physical documents with proof of service. The system may receive uploaded electronic documents for delivery to one or more electronic and/or physical endpoints. After the electronic documents have been received, the delivery system determines whether the received electronic documents should be delivered electronically or physically, based on recipient data in the delivery system. If physical documents are to be delivered, the system may intelligently decide whether to aggregate some documents into a multi-document package. The system provides for delivery by commercial carrier, postal service, and/or electronic delivery. Optional services available to the sender include, but are not limited to, certified mail, proof of service, and email confirmation.