I know this is an old post, but I've recently gone through this process, and this was one of the only sources of information I could find, and wanted to give feedback on my experience for anyone needing to do this in future.
It looks like success here will pretty much be determined by the customer care agent that handles your call. I initially reached out to FCA US customer care, after explaining the situation they wanted to refer me back to FCA Canada. I explained that FCA Canada does not do this, and it needs to be done by FCA US, and the call ended with the support person just saying they cannot help me.
I tried again the next day, pretty much the same experience, with the customer care agent wanting to refer me to the DOT.
On the 3rd attempt I reached a customer care agent that was familiar with the process, they got the required details from me, and created a case with the documentation team for me. Within a couple of hours I got a response from the documentation team indicating they can't help me since my vehicle has open recalls.
I promptly had the open recalls takes care of, contacted customer care again, and they referred the open case back to the documentation team. Within a couple of hours I received an email requesting required documents:
Copy of current Canadian vehicle registration
Proof of insurance showing name and license plate number of individual importing vehicle
Proof of immigration (copy of work or student visa, employment offer)
Proof of U.S. address/current address
Current odometer reading
Once I sent the documents, I got the approved letter in a couple of hours.
I think the important points are:
Continue trying customer care until you reach someone that has knowledge of the process.
Ensure you have the required documents available.
Ensure there are no open recalls on your vehicle.