Thanks. I think I got it figured out. I had to add 127.0.0.1 as a local network in Asterisk SIP Settings.
Is there a more elegant way of being able to have 7 and 10 digit dialing to the same number? In my testing I see I'm having to enter 2 entries for each DID. 1 for 10 digits and the other for 7 digits with a prepended area code. Our PBX is setup to automatically prepend our local area code for 7 digit dialing, but if I enter the full 10 digits in the outbound route, then only dial 7 digits, it doesn't work.