Internal Caller ID passed to Follow me or call forwarding

I feel like I am missing something obvious but when Find Me/Follow Me or Call Forwarding is enabled on an extension and that extension is called from an internal phone the Caller ID that gets passed to the end user’s cell phone is the internal Caller ID of the extension that’s calling (which gets marked as spam by the cell phone carrier) even with the Override Extension set to yes on the Outbound Route that the call is using.

What am I missing here.

I should add that we do not have the Outside CID field set on the individual extensions, this is typically handled by the Outbound route on these smaller systems.

We can go back in and set those manually if that will get us the desired behavior. However, I guess I am seeking to understand the behavior and why this is happening so that I am not just putting a workaround in and moving on without understanding if we actually did something wrong in the initial configuration of the system.