An enhanced email system incorporating mobile wireless communication devices includes program logic for efficiently managing (i.e., at least partially synchronizing) “messages sent” files in the mobile device and in a related message server. The exemplary program logic also more efficiently handles resending of previously sent email messages from the mobile wireless communication device (especially in the context of synchronized messages sent files) by sending to the message server only abbreviated unique message ID in the first instance. In this way, wireless bandwidth is conserved as is the device battery.