I Couldn't Add My Southwest Companion — Reader Mistake Story

Today, I want to share a story from TPG reader Justin, whose travel plans hit a snag when his flight was oversold:

For over a year, my wife and I have been planning a trip to Hawaii for Thanksgiving, so we were naturally excited when Southwest finally announced flights. I was still working toward earning the Companion Pass when the schedule opened, so we bought my ticket with cash and booked my wife's ticket with points, planning to cancel her ticket and add her as my companion later.

By the time I earned the Companion Pass, the flight was sold out. I called Southwest and asked the agent I spoke with if she’d be able to see the inventory and grab it as soon as we canceled my wife's award ticket. The agent said she’d done it before and would be able to see it immediately, but couldn’t guarantee that someone else wouldn’t get it first. Figuring a low probability of that happening in the couple of minutes it would take to process the transaction, I decided to give it a shot.

She canceled the award ticket, but couldn’t see the released seat. She then put me on hold, and I waited nervously for 15 minutes. When she came back, she said the flight was actually overbooked, so the seat never got released. She acknowledged she should have looked to see if it was overbooked before canceling, but claimed there was nothing she could do after the fact.

After speaking to a supervisor and corporate customer service, I ended up with a $100 voucher and the need to buy my wife a ticket on a different flight. I knew there was no guarantee we’d get the seat, but I wish they would have told me there wasn’t even a chance!

One of the few restrictions Southwest imposes on the Companion Pass is that your flight must have an available seat in order for your companion to be added. So long as Southwest is still selling tickets, you should be able to add a companion to your flight regardless of which fare types are available. The problem Justin ran into is that a flight will show zero open seats whether it's exactly sold out or oversold by any number of passengers — you can't tell the difference online. If you're trying to open a seat by canceling a paid reservation, be sure to call customer service first and ask explicitly whether the flight is oversold. If so, you'll need another solution.

Fortunately, other solutions aren't hard to come by, especially if your travel plans are flexible. Southwest has the best change and cancellation policy in the business, so if the flight you want is oversold, you can simply change to another that isn't and pay only the difference in fare. If your plans aren't flexible, then keep checking your original flight (the more frequently, the better) and be ready to pounce on any seat that opens up. Passenger counts can change quickly in the last 24 hours or so before travel, and since you can cancel a Southwest reservation until 10 minutes before departure, there's no harm in continuing to search. One thing you shouldn't do is book yourself on multiple flights as a backup plan, since Southwest will likely cancel duplicate reservations.

Related: How to Use the Southwest Companion Pass

I appreciate this story, and I hope it can help other readers avoid making the same mistake. In appreciation for sharing this experience (and for allowing us to post it online), I’m sending Justin a gift card to enjoy on future travels, and I'd like to do the same for you. Please email your own travel mistake stories to info@thepointsguy.com, and put "Reader Mistake Story" in the subject line. Tell us how things went wrong, and (where applicable) how you made them right. Offer any wisdom you gained from the experience, and explain what the rest of us can do to avoid the same pitfalls.

Feel free to also submit your best travel success stories. If your story is published in either case, I’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can't respond to each story individually, but we'll be in touch if yours is selected. I look forward to hearing from you, and until then, I wish you a safe and mistake-free journey!