We checked out yesterday. We always take Magical Express and have never had a problem.
We had 5 pieces of luggage between the four of us. We always bring one piece each, then a 5th in case we go over with souvenirs/a place to pack shoes, etc.
Because flights go so fast during the holidays, I called Southwest to book us all at once, rather than each member of the family booking their own flight. One year we got halfway through booking and the flight sold out. So we were all on the same reservation.
Now, my dad and I share the same name. As a result, I use my middle initial and "JR." on my credit card, when booking flights, etc.
We go to check our luggage at Beach Club yesterday and the staff collecting it is obviously overwhelmed. I heard one member of the staff say "we're running out of room on the truck."
So we get up to the desk finally and they weigh the luggage. My mom's luggage goes over, so we shift some stuff around. The employee proceeds to check us in and says "we only have two members of the family listed." My heart drops for a moment. I collect myself and remember that SW checked us in yesterday for the flight—24 hours before departure. I correct the gentleman, saying "no we have 4 tickets" and show him the reservation.
He eventually calls over the manager and she informs us that because my dad and I have the same name, the system is glitch-ing and not allowing her to log us in. Because of this, she can only check in my sister and mom. Okay—fine, I'll check in at the airport then. She then says that she can only take four bags and we'd have to bring the fifth with us, as there's a maximum of 2 bags per person. Here's where we got a little annoyed. We go back and forth for a little while, and they ultimately blame SW. They were a bit nasty with my family. Even the gentleman who weighed our bags apologized for the other employees. What really bothered me was after having to once again sort around our luggage, the employee said "make sure you weigh this again, then smirked at us."
I called SW after and the employee said "I don't understand how they couldn't distinguish the two of you—you both have separate ID numbers and your middle initials separate the two of you." She then remarked "if I had to guess, they didn't want to take the extra bag."
Long story short - it was a minor hiccup in the day. We checked the bag, checked in for our flight and were on our way...it was just the way it was dealt with that left a sour taste in my mouth. The one employee smirking as he said "weigh it again"—as if to say "we may not take this either." The manager was basically spitting out boilerplate answers you learn in training; we didn't care for the whole situation.
Maybe we're overthinking things and having some first world problems. I think it's a third party service, so I'm not even sure who we'd call or if it's worth complaining.