Note that flagging is done by SW, not the TSA. There was little casual about my initial input. TSA has little to do with Southwest's reservation system besides giving guidelines. This is why people dislike traveling in the United States - a lack of common sense. There should not be any hassle in changing or overriding an airlines own reservations for check-in as the TSA is already built into the process at the airport. Being unable to override system conditions is incompetent database management and creates this sort of inconvenience.
And a TSA redress number is comical - lost in a bureaucracy more involved in creating jobs for a theatrical presentation of security which we all know does nothing but pester, annoy, and infuriate the public while being ineffectual. This is a Southwest reservations problem defined by their database error. The TSA would simply direct you to Southwest's customer service.