Is it worth trying to get American Airlines to give me a voucher for the WiFi/entertainment system being out on a 6-hour flight?

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Unless you have very high status. No

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Just platinum

This happened to me, and they refunded me the cost of Wi-Fi.

Yes, they always give 10k miles if you complain

This happened to me once on United and they gave me $250. I was platinum at the time

It’s a simple email page and will take 3 min of your time to write. What’s to lose here?

If I email them, they usually will issue 5,000 miles to my account, which approximately worth the monthly subscription

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