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My story is very long and complicated and full of conspiracy theories as to what happened so I'm just going to keep it simple and just ask, how can a second time flyer get "red flagged" at the airport at the very front desk even before going through security?

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It is unclear what you mean with ‘red flagged’.
You seem to assume this is a standard term, but it is not - unless you mean an umpire literally throwing a red flag at your feet.

If you mean getting an ‘SSSSS’ written on your boarding pass - it is mostly random selections. I got two of them in about 300 flights over the last ten years - it doesn’t mean anything.

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  • And note that an infrequent flyer very well might be more likely to draw a SSSS than a frequent flyer. Frequent flyers have established a pattern of not doing bad things. Commented Jul 27, 2021 at 3:39

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