Sales Order Email Sending Error message "Unable to send e-mail! Error: 501 5.1.3 Invalid address"

Agent logs into Evolution, processes Sales Orders and sends out to clients. After a few emails have been sent, the agent receives an error "Unable to send e-mail! Error: 501.1.3 Invalid address". The agent has to log off of Evolution and log back on, tries to send the same Sales Order again to the same client, and it sends successfully.