Background: I worked through Sept. of this year and have now retired. My first SS retirement payment was generated 9/30 and showed up in my bank account 10/1. The payment amount included six months of retroactive payments (March thru Aug. 2025, going back to when I reached Full Retirement Age), plus the payment for Sept. My wife will continue working for a few more years, and we file our tax returns jointly.
Questions: Will I need to do a quarterly estimate and payment of taxes going forward, or can I just report my SS income on our annual April returns? If I’ve read correctly, I can just report it yearly so long as my expected tax shortage for the year (Line 24 “total tax” minus Line 33 “total payments” on the 1040-SR) is less than $1000, or if Line 33 divided by Line 24 on Form 1040-SR is at least .90. Is that right?
In our case the 2024 return may not be the best point of comparison, since we drastically adjusted our voluntary withholding amount this year. So, let’s say that I do in fact have to start estimating and paying quarterly. When will my first payment be due? (See dates at the top.) Would I make multiple initial payments, since the benefit period, counting the retroactive payments, spans several quarters?
