A couple years ago we investigated getting a customer with POS locations on to a PIN/Chip Debit and Credit Card machine for SPS, the IPP320 (widely used here in Canada), but their remote locations use a terminal server and no matter what we did the swipe device didn't work through remote desktop. Sage tried to get it working too, with similar results.
Now the customer is asking about this again (complaining about how poor it look for their customers to see them typing in CC information via remote desktop), and since I think the US is rolling out PIN / Chip, perhaps someone else has run into this problem? Any solutions?