Originally Posted by kgsd
Why can't the page be smart enough to know you want to checkin for that itinerary?
This is a known deficiency. Southwest mailed me a technical explanation which I will attempt to summarize. One of the pages is secure (https) and the other is not. I guess there would have to be a special page made for this rather than reusing the existing online checkin page. Anyway, it's not as simple as we users would think.