Serial Modem to update Guide

[hmca]

I am trying to set up a US Robotics Courier Serial modem to update my Guide. I set Sage to auto dial. Yet when it comes time to update, nothing happens. Sage does not wake up from S1. If Sage is awake, the modem is not initialized to dial. The only way I can get it to work is to have the computer at full power, Sage awake, AND the modem already dialed into the internet.
Not sure what is wrong here. Sage wakes from S1 for events and shuts down. I expected Sage to wake for the Guide update, dial the internet, do its business and then shut down.
Has anybody been able to make a similar setup work?

Update: By adjusting some Windows settings I can get the modem to autodial, however when it asks for the password, extra characters are added (Dial2) and my service disconnects. I can enter the correct password and click OK (Dial3) then go right back in and the extra characters are added (Dial4). Yet if I manually click on the dial desktop icon, I can connect with the correct password (Dial1). What gives?