As someone who just went through this transition myself, I can confirm what others have said - the first year is monthly reporting, then it switches to annual. I started collecting in January 2024 at age 64 and had to do monthly reporting all of last year. One thing that really helped me with the seasonal income issue (I do tax prep work too!) was keeping a simple spreadsheet tracking my monthly earnings alongside the SSA forms. When it came time to estimate my 2025 annual earnings, I could see the clear pattern of my busy season vs. slow months. The annual reporting is definitely easier from a paperwork standpoint, but like everyone's mentioned, be conservative with your estimate. I slightly overestimated my 2025 earnings and would rather get a small refund than deal with an overpayment situation. Also, don't stress too much about the transition - SSA will send you clear instructions when it's time to switch to annual reporting. They're pretty good about walking you through the process, even if getting them on the phone can be challenging sometimes!

Welcome to the community! I see you're getting some great advice here. Just wanted to add one more perspective as someone who went through this transition a couple years ago. The switch from monthly to annual reporting is definitely real and happens after your first calendar year of benefits. What I found most helpful was using that first year of monthly data to create a really solid baseline for future annual estimates. Since you're in accounting, you'll probably appreciate having that detailed monthly breakdown to work with. One thing I wish someone had told me earlier: if you end up with an overpayment situation down the road (which hopefully you won't if you estimate conservatively), SSA is generally pretty reasonable about payment plans. They'd rather work with you than create financial hardship. Also, make sure you understand the difference between the regular annual earnings limit and the higher limit that applies in the year you reach FRA - that caught me off guard when I was planning ahead. The SSA website has the current limits, but they do adjust them annually for inflation. Keep asking questions here - this community has been super helpful for navigating all these Social Security quirks!

I'm so sorry for your loss, Benjamin. As someone who works in estate administration, I can confirm what others have said about the "month of death" rule - it's unfortunately very strict. Since your aunt passed in October, her estate won't be entitled to any payment for October (which would have been paid in November). The September payment she received in October was indeed her final eligible benefit. One thing I'd add is to make sure you keep detailed records of all your communications with SSA, including dates, times, and the names of representatives you speak with. Also, if you haven't already done so, you might want to contact her bank to freeze her account temporarily until you can get everything sorted out with the estate. This prevents any potential complications if SSA accidentally issues a payment that would then need to be returned. The whole process can be overwhelming while you're grieving, but you're doing the right thing by getting informed about the rules upfront.

I'm so sorry for your loss, Benjamin. Having gone through this exact situation when my grandfather passed away last year, I can share what I learned. The "month of death" rule is unfortunately very clear - no Social Security benefits are payable for the month in which someone dies, regardless of when in that month they pass away. So since your aunt died in October, her last eligible payment was for September (which she received in October). There won't be a November payment for October. I know it seems unfair since she lived most of October, but that's how the rule works for retirement benefits. When I called SSA to report my grandfather's death, they explained this and also mentioned to watch out for any erroneous payments that might come through, as those would need to be returned. Make sure to report her passing to SSA as soon as possible if you haven't already - they're usually pretty good about stopping payments once notified, but it's better to be proactive. Dealing with all this paperwork while grieving is really tough, but you're asking the right questions.

Based on your situation, the 7% withholding might actually be reasonable given your income sources. With $73K in work income (even if only half-year), $2,450/month SS benefits ($29,400 annually), plus that $650/month pension ($7,800 annually), your provisional income will likely put you in the range where 85% of your SS benefits are taxable. The Child Tax Credit will definitely help offset some liability, but with multiple income streams, you'll probably owe something. I'd suggest using the IRS withholding calculator with your projected full-year numbers - including that upcoming RMD requirement. You can always adjust the withholding percentage if 7% turns out to be too much. Better to have a small refund than owe a large amount plus potential underpayment penalties.

Just wanted to add another perspective as someone who went through this exact situation a few years ago. I also have custody of my granddaughter and was confused about the withholding when I first started getting benefits. What really helped me was keeping detailed records of all my income sources for the first year so I could see exactly how the taxation worked in practice. One thing that surprised me was how much the timing of income matters - since you worked half the year at a higher income level, your tax situation this year will be different from future years when you'll only have retirement income. I'd recommend calculating it both ways (this year with partial work income vs. next year with just retirement income) so you can adjust your withholding accordingly. The Child Tax Credit really does make a significant difference, but with multiple income streams like yours, some withholding is probably smart to avoid surprises.

I went through this exact same situation when I started receiving benefits earlier this year. What really helped me was creating a simple spreadsheet to track all my income sources - SS benefits, pension, part-time work, any investment income, etc. Then I used the combined income formula that @Misterclamation Skyblue mentioned to see where I'd land. In my case, I ended up choosing 7% withholding because my other income sources put me just over the $34,000 threshold but not by a huge amount. The key is being realistic about your total annual income and remembering that you can always make quarterly estimated payments if you find you're still short come tax time. One tip: if you're still working part-time, consider adjusting the withholding on those paychecks too rather than relying solely on SS withholding. Sometimes it's easier to manage that way since you have more control over the exact amounts.

Just want to add another perspective as someone who's been navigating this for a few years now. One thing that caught me off guard initially was how Medicare premiums factor into this equation. If you're enrolled in Medicare Part B (and especially Part D), those premiums are automatically deducted from your SS benefits BEFORE any tax withholding calculations. So if you're getting $2,950 gross but paying $174.70 for Medicare Part B, your actual benefit for withholding purposes would be calculated on the net amount. This can affect which withholding percentage makes sense for you. Also, don't forget that if you have any retirement account withdrawals (401k, traditional IRA, etc.), those count toward your combined income too. I learned this the hard way my first year and ended up owing more than expected despite having withholding set up. The good news is that once you get through your first tax season with SS benefits, you'll have a much better sense of what works for your situation and can adjust accordingly.

Welcome to the community, Gael! I'm so sorry for your loss as well. It's heartwarming to see how supportive everyone is here. When I first joined this community three years ago after my husband passed, I was completely lost with all the survivor benefit rules and regulations. The fear of making a financial mistake that could jeopardize my benefits was paralyzing. But the knowledge and real-world experience shared here by members like Mei, AstroExplorer, and others has been absolutely invaluable. The earned income vs. capital gains distinction that everyone has explained so well in this thread is a perfect example - it's such crucial information that isn't clearly communicated by the SSA. I hope this discussion about property sales gives you confidence to make the financial decisions that are right for your situation. This community truly is a lifeline for navigating these complex waters.

Welcome to the community! I'm also relatively new here and have found this discussion incredibly enlightening. I lost my spouse 18 months ago and have been so cautious about any financial moves because I was terrified of inadvertently affecting my survivor benefits. Like many others have mentioned, the SSA website really doesn't make these distinctions clear at all. Reading about how capital gains from property sales don't count toward the earnings limit is such valuable information - I've been holding off on selling some inherited stock for the same fears that Amara mentioned. It's wonderful to see how this community comes together to share real-world knowledge and support each other through these challenging situations. The expertise and kindness shown here gives me so much more confidence in navigating these complex benefit rules.