Just wanted to add one more perspective as someone who made this exact decision last year. I was earning about $2,500/month from part-time work and ultimately decided to wait until my FRA. Here's what helped me make that decision: I called SSA and asked them to calculate both scenarios - starting benefits immediately with the earnings test vs. waiting until FRA. The difference was more significant than I expected when you factor in the delayed retirement credits AND avoid all the earnings limit complications. The representative also pointed out something I hadn't considered: once you start benefits, you're locked into the Social Security system's administrative requirements. You have to report earnings changes, potentially deal with overpayments, file annual earnings reports, etc. When I reached FRA, all of that disappeared overnight - no more earnings limits, no more reporting requirements, and a higher monthly benefit. Since you mentioned you don't desperately need the income right now, I'd really encourage you to run the numbers with SSA on what your benefit would be at FRA vs. starting now. In my case, waiting 18 months resulted in about $200 more per month for life, plus eliminated all the administrative hassles. Sometimes the peace of mind and simplicity is worth more than getting payments sooner. Whatever you decide, you're asking all the right questions and clearly doing your homework. Good luck!

I've been working with Social Security disability cases for over 15 years, and I wanted to add some clarification on a few points that came up in this discussion. First, the earnings test calculations can indeed be complex, but there's an important distinction many people miss: Social Security uses gross earnings (before taxes and deductions) for the earnings test, not take-home pay. So if you're earning $2,600 monthly in gross wages, that's what counts toward the limit. Second, regarding the "monthly earnings test" in your first year - this is technically called the "monthly earnings test for the year of retirement." It only applies during the first calendar year you receive retirement benefits, and it can be incredibly beneficial if your earnings fluctuate month to month. One strategy I've seen work well: if you do decide to start benefits mid-year, consider timing it for a month when you might have lower earnings (maybe you're taking time off or have reduced hours). This maximizes your chances of receiving full benefits for at least that first month. The key point several people made about proactive communication with SSA is absolutely correct. The worst situations I've seen are when people don't report earnings changes promptly. SSA can and will recover overpayments, sometimes years later, and it's much more stressful to deal with retroactively. Given your steady $2,600 monthly income and FRA in 2026, waiting does seem like the cleaner option, but definitely get those official calculations from SSA to make an informed decision.

KEEP COPIES OF EVERYTHING!!!! I learned this the hard way. SSA lost my application TWICE and then tried to charge me penalties because they said I didn't apply on time even though I DID!!! Take pictures of all documents with your phone before you submit them and get names of everyone you talk to. The system is a MESS right now!!!!

I'm dealing with something similar right now! My husband and I applied for Medicare at the same time last month, and I got my approval letter but he's still waiting. What I learned from calling SSA multiple times is that even when you apply on the same day, your applications can go to different processing centers or even different workers within the same office. The key thing is figuring out if there will be any gap in coverage when you retire. Since you're retiring in January and he's on your employer insurance, you need to know EXACTLY when his Medicare will start. If there's even a day without coverage, the medical bills could be devastating. Here's what helped me: I called SSA and asked them to check if his application needed any additional documentation or verification. Sometimes they're waiting for something specific but don't always tell you upfront. Also, since you're both over 65 and currently have employer coverage, you should be eligible for Special Enrollment Period rules, which are different from the regular enrollment periods others mentioned. Don't wait for February - call back this week and be persistent about getting specific dates and any missing requirements!

Hey Dylan! I'm actually in the middle of researching this exact same thing right now. From what I've gathered reading through all these comments, it sounds like the rollover itself won't hurt your SSDI, but man, the tax implications are something else! I'm leaning toward doing a partial rollover strategy like Rudy mentioned - maybe convert a little bit each year instead of doing it all at once. That way I can keep my taxable income more manageable and avoid getting hit with those Medicare premium increases. One thing I'm still trying to figure out though - does anyone know if there's a specific dollar amount that's considered "safe" to convert each year without triggering any red flags? I've got about $45k in my traditional IRA and I'm trying to map out a 3-4 year conversion plan. Thanks for starting this thread - it's been super educational reading everyone's experiences! 👍

Hey Dylan! I just wanted to chime in as someone who's been on SSDI for about 4 years now. The advice from Sofia and Rudy is spot on - the rollover itself won't affect your SSDI benefits directly since it's not considered earned income. But definitely watch out for those tax implications! I made a similar move about 2 years ago and learned the hard way about the Medicare premium thing. Ended up with higher Part B premiums the following year because my MAGI spiked from the conversion. Not the end of the world, but definitely something I wish I'd planned for better. My suggestion would be to sit down with someone who really knows this stuff before you pull the trigger. The SSA rules can be tricky, and while the folks here have given great advice, having a professional look at your specific situation could save you some headaches down the road. Also, if you do decide to go ahead with it, keep really good records of everything. The SSA might ask questions later, and having all your documentation ready makes life so much easier. Good luck with whatever you decide! 🙂

I'm going through this exact same situation right now! Just reached FRA two months ago and applied online while still working. Got the same confusing W-2 request and was convinced I'd messed something up during the application process. Reading all these responses has been incredibly helpful - it's clear this is just their standard procedure when they need current earnings data that isn't in their system yet. I love that there's a dropbox option at local offices! That would save me from having to schedule time off work or sit on hold for hours. Planning to stop by my local SSA office this week to drop off my recent paystubs. It's frustrating that the online application doesn't explain this better upfront, but at least now I know it's not going to delay my benefits since we're already at FRA. Thanks everyone for sharing your experiences!

I'm dealing with this exact same situation right now! Just turned 67 last month and applied online while still working full-time. Got that same confusing request for W-2 or paystubs and was totally panicking that I'd messed up my application somehow. Reading through all these responses has been such a relief - it's clear this is just standard procedure when SSA needs current earnings data that isn't in their system yet. I really appreciate everyone sharing their experiences and solutions. The dropbox option sounds perfect since I can't easily take time off work, and knowing that several people got through by calling early morning gives me hope I won't have to wait 2+ hours on hold. It's frustrating that the online application doesn't explain this better upfront instead of making it sound like some urgent requirement, but at least now I know my benefits won't be delayed since I'm already at FRA. Thanks to everyone who shared their stories - this community is so helpful!

As a newcomer to this community, I've been following this thread closely as I'm considering early retirement next year and have been worried about how my small business income might affect Social Security benefits. Reading through everyone's experiences has been incredibly educational! One thing I'm curious about that hasn't been fully addressed: for those of you who have S corps with rental properties, how do you handle the timing of reporting to SSA? Do you report your expected salary at the beginning of the year, or wait until you know your actual earnings? I'm particularly concerned about accidentally under-reporting and then having issues later if circumstances change. Also, @Andre Dubois - have you been able to connect with SSA yet using the Claimyr service that @Liam O'Donnell mentioned? I'm very interested to hear how that goes since I've had similar frustrations trying to reach someone by phone. Thanks to everyone who has shared their experiences here. This thread has been more helpful than hours of trying to research this topic on my own!

As a newcomer to this community, I want to thank everyone for this incredibly detailed discussion! I'm in a similar situation - just turned 64 and considering early retirement with an S corp that owns a few rental units. Reading through all these experiences has been more valuable than any official SSA publication I've found. One aspect I haven't seen mentioned yet: has anyone dealt with SSA's position on S corp owners who occasionally handle emergency repairs or tenant issues themselves? I'm wondering if even minimal hands-on involvement (like dealing with a plumbing emergency when the property manager isn't available) could jeopardize the passive status, or if SSA considers this normal property ownership rather than "substantial services." Also, for those who have successfully navigated this process, do you think it's worth consulting with a Social Security attorney upfront, or is the DIY approach with proper documentation sufficient for most straightforward rental situations? The collective wisdom in this thread gives me much more confidence about moving forward with my retirement plans. Thank you all for sharing your real-world experiences!