How do I config a Polycom IP500 for two diff servers?

I have an IP500 configured with Line 1 for my Asterisk server. I’d like to configure line 2 to log into another Asterisk server at a remote location. I know the firewall stuff is working because I can log a softphone into the remote * server just fine. I’ve accessed the IP500 via the web interface and “think” I entered all of the correct stuff but it never even tries to contact the remote server. I turned on sip debug and even tcpdump and the phone never even tries. What am I missing???

I assume you were refering to running sip debug and tcpdump on the remote server and not seeing any traffic. Did you configure the proxy for the second line to use a host name or IP address? If host name, can the polycom resolve that hostname on your network? If the proxy is correct, and the correct ports are open between the servers, even if the username and password were incorrect you would see a REGISTER request at the remote machine. If you are not seeing it them something is blocking port 5060.

Now some may say, use IAX trunking between the asterisk boxes and jut register the phone locally and extend your dial plan to include reaching the extension on the other server.