Originally from ticket #3839.
Outbound caller ID is not being sent on transfers.
After doing some testing, this is what I see.
If it is a blind transfer, as in the receptionist presses transfer before the other end answers, the caller ID info will transfer.
If it becomes an attended transfer, where you talk to the receptionist or answer before she hits transfer the second time, the caller ID will be her info.
This is due to the call being completed between Extensions and the transfer happens afterwards, so the system does not send it.