Caller ID passthrough without an extension involved

I have a scenario occurring and I am unable to figure out what I'm missing.

I'm running 7.3.3.6

I have a customer with 100 extensions all over the state. I apply a different caller ID to every extension.
When a call comes in and they transfer it out or use find me-follow me the original caller ID passes through. (use original caller id box is checked off on each extension in their own settings)

This is all good and I'm having no issues here.

My issue happens when a phone is set to use the phones build in call forward button. The call will forward but isn't connected to any specific extension so it grabs the tenants global caller ID setting rather than sending the original callers caller ID through.

By looking at the forums I found the global setting in:
Cluster Management-->Telephony Settings-->Default Values-->Outbound Dialing-->(global checkbox) Use original callers caller ID on forwarded calls

I checked this box, but the issue persists and it is still using the tenants global caller ID for these forwarded calls.

I also tried different scripts for outbound dialing with the same results.

Looking for any ideas or other scripts that might help me.