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!

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!

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! 🙂

OMG ppl are so lucky with military pensions! My dad worked for the county for 35 years and gets a good pension but when he tried to get any SS from my moms record they said nope because of that GPO thing. makes no sense why military is treated different from other govt workers!

As someone new to understanding Social Security benefits, this thread has been incredibly helpful! I'm in a somewhat similar situation - my spouse worked for a state agency that didn't pay into Social Security for most of their career, but I've been in the private sector my whole working life. Reading about how military pensions are treated differently than other government pensions really clarifies why we're facing the GPO reduction while military families like yours won't. It sounds like you and your husband are in a much better position than I initially thought when I saw your question. The key takeaway I'm getting is that the type of government service really matters - if Social Security taxes were paid during that service, then GPO doesn't apply. Thanks to everyone for sharing their experiences and knowledge!

I'm still waiting for mine too! It's been really stressful not knowing the exact amount, especially since we're trying to finalize our holiday spending budget. My sister got hers two weeks ago and we usually receive all our SSA mail around the same time. Reading all these responses really puts my mind at ease though - sounds like this is completely normal and they really do send them out over several weeks. I'll stop checking the mailbox obsessively every day and just wait patiently until mid-December like others suggested. Thanks everyone for sharing your experiences!

I'm also still waiting for my COLA letter and was getting really worried until I found this thread! My neighbor got hers almost two weeks ago and we're both retirement age with similar circumstances, so I couldn't understand the delay. It's such a relief to hear from everyone that SSA really does send these out in waves over several weeks. The 2.5% calculation tip is super helpful - I just did the math and it looks like my monthly benefit should go up by about $47. I'll stop stressing about it and wait until December to check my MySocialSecurity account online. Thanks to everyone who shared their experiences, especially the former SSA employee who explained the process!