It depends on your carrier.    With some carriers, such as Verizon SIP, you do 
this using P-Asserted-Identity.  With Verizon SIP, if they can’t figure out how 
to bill the call, it will be rejected.
With Level 3 SIP, you can use From: or PAID but if the number you present to 
them is not on your account, they will bill the call against the “failsafe” 
number on your account.

From: [email protected] 
[mailto:[email protected]] On Behalf Of Positively 
Optimistic
Sent: Thursday, June 26, 2014 10:11 AM
To: Asterisk Users Mailing List - Non-Commercial Discussion
Subject: [asterisk-users] CLID Presentation & Billing Number | Diversion vs. 
Remote-Party-ID vs. P-Asserted-Id vs. From vs. P-Charge-info

We would like to present a toll free CallerID when making outbound toll calls.  
In the past, when our PRIs were directly connected to a Nortel CS1000 we could 
do this, without issue.  Now that the PRIs are front ended by a mediagateway 
facing asterisk, we can no longer do this.

Is it possible to set the billing number via a SIP header and set what should 
be presented as callerid as another header for presentation?

We can't possibly be the only people in the world that has faced this 
challenge.   Searching the internet has provided limited results.
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