ok, I have it working now, I think that did the trick. Now the issue is that when I point my primary number(trunkline) Open Inbound Route to the custom app name, all I get is a busy signal.
I have my custom app configured like this: (I have the span set to "Both")
exten => *101*,1,Answer()
exten => *101*,2,System(rm -rf /tmp/test.wav)
exten => *101*,3,System(swift -n Allison -o /tmp/test.wav -p audio/sampling-rate=8000 "Another test. ${CALLERID(num)}")
exten => *101*,4,Playback(/tmp/test)
exten => *101*,5,Hangup()