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Has anyone’s companion ever received a confirmation email for a flight but when they tried to check in, their reservation was nowhere to be found or was canceled by southwest? If so, did you receive any kind of compensation for the inconvenience?
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First, are you talking about a Companion (flying with a Southwest Companion Pass holder) or just a friend who was also flying on the same flight?
Was the flight changed at any point? That might have caused the Companion to drop off the itinerary or get lost through some kind of glitch, especially if Southwest made the flight change. (If the CP Holder made a change, perhaps they neglected to add the Companion back after?)
In any case, hopefully Southwest was able to straighten things out and get both people back on the desired flight?
Your best bet is to reach out to Customer Relations after the completion of travel to express your disappointment.
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Did the companion have any other flights booked that might have overlapped or been flagged for being "impossible" connections?