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I just earned my Companion Pass last week, and named one of my kids as my companion. We already had a trip booked, with his ticket paid for, and I called Southwest to change his paid ticket to a Companion Pass ticket. They did, and I got his Conf # via email.
Next day when I went to look at flight details on website, the button "Add Companion" to that flight was still there! (As opposed to "see companion details.")
I got nervous, clicked, and was somehow able to book another Companion Pass for that same flight.
If I ignore all of that and check on his flight using the original Conf# from the phone booking, I see those details. If I just start from my actual flight, I see the new Conf # from my panic booking.
So he has 2 conf # , 2 Companion Pass flights booked, both attached to my one flight.
Do you think it matters which one I cancel?
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It probably doesn't;t matter, but I would cancel the one tied to the CP that expires first. You can;t have 2 CPs. Southwest will certainly honor the one that lasts the longest.