Outbound Messages Not Appearing in Monitor Target Mailbox

For VPOP3 to monitor outbound messages it needs to be able to work out that the message is FROM: a user whose mail should be monitored. To do this it has to examine the FROM: address in the message header.

If the message is FROM: fred@domain.com, VPOP3 will look to see if fred@domain.com is a local user or not.

Note: if you use some form of SMTP authentication (either POP3 before SMTP authentication or full SMTP authentication), then VPOP3 will use the login name to decide whether it should monitor the message, instead of using the FROM: address. (n.b. some email clients do not support SMTP authentication)