Two things seem wrong.
First, since the call didn’t match the ‘new’ Inbound Route, it should have matched the ‘old’ route with DID Number 4105555555 and CallerID Number left blank. Did you accidentally delete or change that?
Next, I suspect that the caller ID was sent in a different format from what you entered. The trunking provider may have sent 14105555545 or +14105555545. After you fix the first problem, see what is shown for caller ID in the CDRs, then edit the new route to use that exact format.
If that’s not your issue, turn on pjsip logging and paste a new log.