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Each time I try to book a flight using travel funds I can never do so because of something in the system with the way my name is spelled. I type my name, copy and paste exactly how it is in my account and never any luck. Each time I have to call and by the time I get someone on the phone, the airfare cost has increased. Currently on hold for the last 20 minutes and I am expected to be on hold for 81 minutes. Ridiculous! Does anyone else have this issue?
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Is your middle name included some reservations and not others?
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You could try reaching out to Southwest on Facebook or Twitter to see if they know what's causing the error.