I had the Kobo desktop software (latest version) on my computer, and when I connected the Kobo it told me there was an update available for the reader and installed it.
I'm sure it could have been done just through being connected to WiFi, but I never got a chance to test that.
I'm in Sweden, so out of USA. Just pointing that out to highlight that it works outside us/Canada.
Edit: Link to Kobo desktop
http://kobobooks.com/desktop