Well, Garmin can't, that's for sure
My 660 needs to have something like 'Import Data' clicked, but there is also a message like 'New Media Found'. It's not 'media' but can't remember what it says. I've got my Garmin with me but not my laptop so not much help I'm afraid.
There are much better options for uploading than the dreadful BaseCrap if that is what you are using.
A much simpler way is simply to drag and drop the file onto your device with it connected to your 'pooter.
Good luck.....