Contributing to a 529 plan is not a qualified education expense. But up to $10,000 of High School tuition would be. If the withdrawn overages are used for high school tuition they don't even have to be reported. Just save the 1099s and the receipts for the expenses and you're set.
If your kid is not in private school or you pulled way more out than his cost of schooling per year then this gets harder. So I hope he is.
If he's not-
1) Yes. You need to amend the returns to reflect the penalties due each year. But you didn't pull out the money until 2021 so all of the penalty inducing balances just roll forward each year with new penalties added on. This is going to be a complicated tax return so my recommendation is to file an extension and find a tax professional.
2) The 1099-Q forms do have the appropriate year on them - the year you pulled the money out. The penalty occurs while the money is in there. When you pull it out it stops. It's been building up since 2018. You'll roll the total amount forward, year to year, and then remove the total in 2021.
I answered the other questions already. Good luck. I hope your kid is in private school.
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