Outlook Will Not Go Into Offline Mode

[Steve]

I have an end user who travels frequently and likes to type emails when he is
not connected to the LAN. Before, when he was not connected, he was able to
compose an email and it would go to the Outbox and then be sent out when he
connected to our network via VPN. He did this by clicking the Work Offline
option in the lower right corner of the Outlook screen (OL2003). Now, it
reads disconnected. When he clicks on Work Offline, no check mark appears
and when he composes an email offline and clicks send it hangs the
application. He is running Outlook 2003 in cached mode to our Exchange 2003
SP2 server.