does an over the shoulder bag count as a personal item

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Answering Readers’ Questions: What counts as a personal bag when flying?

I recently got an interesting question from a reader: I’m going on my first business trip next month. I know I am going to carry-on, and my the first bag is a rollerboard. My question is, what exactly counts as that second, “personal” bag? A laptop bag? A shoulder bag? Or does it have to…

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