The What-if worksheet didn't work for me to estimate 2026 taxes because I could not force it to change some numbers it already had from 2025. But the Estimated Tax worksheet did work - it looks like...
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The What-if worksheet didn't work for me to estimate 2026 taxes because I could not force it to change some numbers it already had from 2025. But the Estimated Tax worksheet did work - it looks like we will meet both safe harbor provisions (90% of 2026 taxes and 110% of 2025 taxes) so don't have to worry about underwithholding. We're very close to the $1000 taxes due at filing provision (slightly over) so I'll make a small estimated payment in April and if our interest is more than I estimated, or we convert more than planned to a Roth, I'll make estimated tax payments in those quarters too (for example, when CDs mature), or the 4th quarter. As long as we fall under one of those safe harbor provisions, we shouldn't have to worry about having more income in the first quarter than the others. I still can't figure out how you would plan estimated tax payments per quarter to make up for underwithholding that quarter, because it seems that paying taxes on a $500K income based on $125K earned in the first quarter would result in a huge refund if your income for the year ended up being $250K (especially if your employer kept withholding at the 22% rate). Nobody's going to give the IRS an interest-free loan like that. The only practical reason for paying a huge estimated tax payment in the first quarter that I can see would be if most of your income was received in the first quarter (say an RMD you take in January because it's based on end-of-year account balance and you're afraid the stock market is going to go down later in the year) and not enough was withheld, and you know that the income (such as interest and taxable pension, SS benefits, etc.) received throughout the rest of the year was going to be much less, even though you have taxes withheld from that so it wasn't going to make up for the RMD at the beginning of the year and you wouldn't meet the safe harbor requirements.