Change the CallerID of the extension when dialing out
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You may have the need to call out using different CallerID, some of them may be not even defined in the system. There are multiple ways to do it, let's review them:
Use CallerID regex
If you have some "rules" for choosing the CallerID, you may use the CallerID regex located in the DIDs screen
and then associate the Outbound CallerID regex created to your extension. This way you can use an Italian CallerID number when dialing a number starting for 39 or use an American number when dialing a number starting for 1
Use a feature code
You can easily create a feature code for each of your custom CallerID. Start by creating a Custom Destination, type "Alter CallerID number" for each one of your custom CallerID