This whole thread has been incredibly educational! I'm 64 and just started collecting benefits this year while continuing to work part-time. Reading about Cole's eBay situation made me realize I need to be way more careful about tracking ALL my income sources, not just my main job. The point about net vs. gross income for self-employment is huge - I do some consulting work on the side and was definitely thinking about it wrong. And I love the idea of monthly spreadsheet tracking that GalacticGuru mentioned. That's so much smarter than trying to figure it all out at the end of the year. It's also really reassuring to see that SSA was willing to work with Cole on payment options when he was proactive about reporting. Shows that being upfront and calling early really does make a difference in how they handle these situations.

This has been such an incredibly helpful discussion! As someone who's 65 and considering starting Social Security benefits next year while keeping my small Etsy jewelry business running, I'm taking notes on everything shared here. The biggest takeaway for me is definitely the net vs. gross income distinction - I would have absolutely made the same mistake as Cole initially. And the monthly tracking system that several people mentioned is brilliant. I'm going to start implementing that right away, even before I begin collecting benefits, so I have a good baseline. What really stands out is how much better the outcome was when Cole proactively called SSA rather than waiting for them to discover the overage. The fact that they offered him flexible repayment options shows that being honest and upfront really does make a difference in how these situations are handled. For anyone else running online businesses alongside Social Security, this thread is a goldmine of practical advice. Thanks to everyone for sharing their real-world experiences!

As someone who's been through the SSA application process recently for other benefits, I wanted to add a practical tip that might help everyone preparing for this. When you gather your documentation, make multiple copies of everything and organize it in a clear folder with tabs. SSA offices can be overwhelmed and sometimes lose paperwork, especially during periods like this when they're dealing with new legislation. Also, if possible, try to apply in person rather than online or by phone for these complex cases. The representatives can walk through your specific situation and make notes in your file about the unique circumstances. Online applications might not have the right fields or options for explaining the GPO repeal situation. One more thing - keep detailed records of every interaction you have with SSA, including dates, times, representative names, and what was discussed. If there are any issues or delays, having that documentation will be invaluable if you need to appeal or escalate your case. I'm really hoping SSA handles these retroactive cases fairly. There are probably thousands of people in similar situations who deserve these benefits they were essentially forced to give up due to GPO.

I'm new to this community but found this discussion incredibly helpful as I'm in almost the exact same boat! My wife was a librarian for our county school system for 22 years, and when I passed away... wait, sorry, I mean when her first husband passed away in 2020, she never applied for survivor benefits because we knew GPO would eliminate them completely. Reading through all these responses has given me so much hope and practical guidance. The tip about bringing a copy of the legislation and applying in person rather than online is something I never would have considered but makes total sense given how complex this situation is. One question I have that I didn't see addressed - does anyone know if there's a specific order we should follow when gathering the documentation? Like should we request our spouse's Social Security statement first, or get our pension documentation together first? I want to make sure we have everything properly organized before the law is signed so we can move quickly. Also, has anyone considered reaching out to their congressional representatives' offices? Sometimes they have caseworkers who can help navigate SSA issues, and since this is new legislation they might be particularly willing to assist constituents who are affected by the changes. Thank you all for such a thoughtful discussion - it's given me a clear action plan for helping my wife finally get the benefits she's been entitled to all along!

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.