A mail address can never be secured by SSL/TLS. Instead, the connection between client and server can be secured. If you have a valid certificate for your Plesk host name installed and if the client connects to POP, IMAP and SMTP using SSL/TLS and the host name (not the individual domain name of the subscription), then the connection is automatically properly secured. If the client is not connecting by using the host name of the host where the SSL certificate is installed, the connection is insecure. If the client is using the host name where the SSL certificate is installed, but is using SSL/TLS, the connection is insecure. For SSL to work you do not need to set an SSL checkbox in Plesk's mailbox configuration. If the host supports SSL, clients can use SSL when connecting to the mailbox. They must meet the conditions named in this post to properly establish a secure connection, though.