Basically the canadian portal for Kayak was getting the southwest fares, while the US version did not.
Kayak usually does not get southwest fares, as they don't publish them to Kayak, expedia, etc.
Perhaps Kayak was running a test in Canada of scraping the southwest fares off of their website.
In any case, I doubt it has anything to do with searching from the originating city.
(Besides, why would Kayak do that? They want to present a cheapest price to get you to buy tickets - they make a fixed fee on the booking no matter what the price is)