Thank you @Earlybird for the info. The Fidelity associate kept insisting that they don't report trustee-to-trustee transfers and qualified withdrawals to IRS. It does sound dubious because how do they know it is a qualified transfer or withdrawal. I am trying to get it in writing, but Fidelity hides the feature to send them message very well. They want me to call or chat with their virtual or live agents.
Also, for your reference. I made three 529 to Roth IRA transfers for my two sons and my daughter in 2024. My two sons 529 accounts are with Fidelity, and they got one right (issued to the beneficiary) and one wrong (issued to me).
For my daughter, I paid tuition and made a 529 to Roth IRA transfer. She just graduated, and the transfer met the rules (held for > 15 years, last contributed > 5 years ago, etc.). I received two 1099-Q forms from the firm where her 529 account is held. One to my name and SSN for the tuition withdrawal (box 4 unchecked and box 6 checked). One to her name and SSN for the Roth IRA transfer (box 4 checked and box 6 unchecked).
Thanks again. I will let you know if I get Fidelity to respond in writing that they don't report the 529 to IRA transfers to IRS.
