Apparently I’m a bit of of an idiot. After following your advice and digging 
through countless other forums, turns out I had “fromuser” set in my sip.conf. 

That being said, in playing I did discover the following. Not sure if this is 
of interest to anyone:

In Asterisk 1.8, you can set sendrpid to yes or pai. These produce 2 different 
SIP headers:

sendrpid=yes
Remote-Party-ID: “8888888888" 
<sip:9056337399@mysipprovider>;party=calling;privacy=off;screen=yes

sendrpid=pai
P-Asserted-Identity: “8888888888" <sip:9056337399@mysipprovider>


These are both produce from the following extensions.conf code:
  same => n,Set(CALLERID(num-pres)=allowed)
  same => n,Set(CALLERID(num)=9056337399)
  same => n,Dial(${IPHONE_away},25,kt)

Where 8888888888 is the CID of the incoming call that I’m trying to redirect 
outwards.

Hope my bungling at least helps someone!
   S.


> Shamus,
> 
> I just tried this with my provider with setting the callerid to 'num' 
> 4025551212 and 'name' Abelbeck
> 
> I made a call searching for that number in SIP packets on my external 
> interface...
> 
> $ sipgrep -d eth0 '4025551212'
> 
> I got a lot of hits like these: (where 1.2.3.4 is my public IP address)
> --
> From: "Abelbeck" <sip: 4025551212@...>;tag=as58ab2497.
> 
> Contact: <sip: 4025551212@...:5060>.
> --
> The incoming callerid was as expected, 4025551212.
> 
> I would examine your outbound SIP context to make sure it is not setting any 
> callerid values.  Your Dial of
> --
> Dial(SIP/8888888888/9999999999,25,kt)
> --
> is no doubt obfuscated, my Dial was...
> --
> Dial(SIP/obfuscated/4025559999,120,K)
> --
> 
> BTW, for an outbound call to your provider I would expect to use options 'KT' 
> instead of 'kt', but doubt that is related in any way to callerid.
> 
> So look at your obfuscated '8888888888' sip.conf context, if you don't have 
> the following you may try adding...
> --
> trustrpid=yes
> sendrpid=yes
> --
> 
> Lonnie


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