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If I pay for the upgraded boarding at the counter on the first leg of the flight does that upgrade me for the second leg also?
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No.
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That's surprising... Do they offer the ability to upgrade both legs at the first departure point or would you need to inquire about an upgrade for the second leg during the layover?
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Solution
You have to check at the counter on your layover. Upgraded Boarding is only available if there are open, unsold BS positions, and Southwest would prefer to keep those actual BS positions available for purchase as late as possible.