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This tutorial shows how to setup an Asterisk server and spoof your caller ID to whatever you'd like. It should take about 50 minutes to run through all these steps. Some of these steps take quite a long time, so I've sped up those portions of the video.
This should all be able to be done on Windows as well, since there are Windows versions of X-Lite and VirtualBox.
All of the account logins used in this video were wiped after it was recorded, so don't bother trying to use them in your own Asterisk server.
Oh, and enjoy the test call made to a tech support scammer at the end, around 35 minutes in.
Here are all the links used in the video, in the order they were used:
www.virtualbox...
www.ubuntu.com/...
askubuntu.com/q...
www.chiark.gree...
www.ringroost....
github.com/GoT...
www.counterpat...
gotrunk.com
Here is the script for easily changing the caller ID:
pastebin.com/wY...