Hi, This response will probably be not much help. My strategy was to do the Roth conversion over 4 years to prevent bracket jump (it didn't work, I'll explain later). The first year I did the conversion in December and had Federal and State penalties which weren't large enough to bother with the ridiculous and confusing paperwork necessary to rescind the penalties. Anyway, the second year I took the conversion early (February) and instructed my pension and SS to increase withholding to cover expected taxes. It would have worked but I based my taxes on the "effective" tax rate that TT calculates for us. However, the conversion increased "effective" tax rate by a few percentage points so I still owe Federal and State taxes, but no penalty on the Federal because I met the requirement of paying in 2025 - 100% of what I owed in 2024. Still owe a small penalty for State taxes. Depending on this years market, I may bite the bullet and complete the conversion rather than dragging it out a few years. If I read you're posting correctly, I don't understand why would have a penalty for underpayment and a refund but maybe I am misunderstanding what you wrote. Good luck, DR
