Had a family SW flight to Midway connecting to an Airtran flight to Jamaica, and of course, you can't check in online at T-24 because of the passport issue.

So naturally, we ended up in high C. Fortunately, my kids are young enough that we took the "family boarding" option.

I think this situation requires a policy decision. I'm not expecting reserved seating, but if your itinerary doesn't allow you to check in online, there should be an auto-processing at T-24 to assign a boarding group. Base it on when the ticket was purchased, or connecting flight times, or something.

I don't mind the seat-roulette game too much, but the system prevents me from playing the game on international flights.

Has there been any discussion from SW about how they are going to handle this?