Will my boss know when I used my employee benefits to fly? Is there somewhere I can view my past flight history where I used my benefits?

I work for Piedmont airlines under American Airlines.

YES Airline management knows when their staff uses their flight benefits.

You can't remember where you went?
Check with you benefits person

Anyone with access to the reservations system can pull up your information.
Unless you're missing work because you flew somewhere and couldn't get a seat back in time, there's no reason for your boss to care.
But yes, the airline does have a master record of when you fly non-rev and your buddy passes. Remember, if your friends use a buddy pass and makes an *** out of themselves, you could be fired.

Access is almost certainly restricted, on request you manager may be able to see where you have last travelled, but not sure why they would be remotely interested.

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