I've got essentially the same thing working fine using IAX2 over openvpn 
instead of SIP.  I'm not the best at debugging asterisk problems but if
the SIP connection is working fine otherwise then I would suspect the
connection is getting there and having problems because it's ending up
in a context that doesn't know what to do with it.




> Asterisk Server 2 -- extensions.conf
> [outbound]
> exten => _9XXXXXXXXXXX,1,       Dial(SIP/outbound-server/${EXTEN:1},30,r)
> exten => _9XXXXXXXXXXX,2,       HangUp()
>
> Asterisk Server 2 -- sip.conf
> [outbound-server]
>         type=friend
>         username=outbound-server
>         secret=********
>         context = all-calls
>         host=1.1.1.1
>         nat=no
>         canreinvite=no
>         insecure=very
>         qualify=yes
>         disallow=all
>         allow=ulaw
>         allow=alaw
>         allow=gsm
>
> any help is accepted and appreciated.
>
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-- 
  Matthew Harrell                          A person who smiles in the face of
  Bit Twiddlers, Inc.                       adversity probably has a scapegoat.
  [EMAIL PROTECTED]     
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