Hi Casey,
Couple of things worth trying:
On your slave computer:
1. open Input Director, switch to the "Global Preferences" tab and check that a) it is set to Run on Startup as well as b) on start it is "enabled as a Slave"
2. The prompting may be caused by your master computer being allocated a new ip address everytime it starts. Open Input Director, switch to the "Slave Configuration" tab. If you're running your computers on your own private network, then you can try the option "Allow any computer to take control". Alternatively, you can check the option "Allow computers only on this subnet to take control" - make sure if you try this that you click the "Select from list" button and select your network.
Regs,
Shane.