One thing I haven't seen mentioned yet is that you'll want to keep detailed records of all your survivor benefit payments leading up to January 2025. When SSA calculates your retroactive payment, they'll need to verify exactly what you received each month to determine the correct difference. I'd recommend downloading your Social Security statements and keeping copies of your benefit deposit records. Also, if you have any questions during the application process, don't hesitate to ask the SSA representative to walk through the calculation with you step by step - they should be able to show you exactly how they're determining your retroactive amount. Having everything documented will help ensure you get the full amount you're entitled to and can help resolve any discrepancies quickly.

Just wanted to add one more consideration that might be helpful - when you apply in January, make sure to ask the SSA representative about any potential Medicare Part B premium adjustments. Since your monthly Social Security benefit will increase by $1,400, this could affect your Medicare premiums if you're already enrolled or planning to enroll soon. The income increase might push you into a higher IRMAA bracket, but since you're switching from survivor benefits to your own earned benefits (rather than getting a windfall), there may be ways to address this. It's worth asking about during your application appointment so you're not surprised by any premium changes later.

I'm dealing with this same frustrating situation right now! I've been trying to get through to SSA for my Medicare enrollment for over a week. The wait times are absolutely insane - I've been disconnected twice after waiting over 2 hours each time. One thing that's helped me stay somewhat organized while going through this process is keeping a call log with dates, times, and how long I waited before giving up or getting disconnected. It's maddening but at least I can track patterns. I'm definitely going to try that 8 AM sharp strategy everyone keeps mentioning. Has anyone had success with the local SSA office phone number instead of the national 800 number? I'm wondering if calling my local office directly might have shorter wait times, though I know they probably route everything through the same system anyway. Also, for anyone else in this boat - make sure you're calling from a phone that won't automatically hang up after a certain time on hold. I learned that the hard way when my cell phone cut me off after 2 hours!

I just went through this exact same struggle three weeks ago! After multiple failed attempts with the phone system, I found a combination approach that finally worked. First, I started the Medicare application online at ssa.gov (under "Apply for Benefits" > "Medicare Only") which at least got something in their system. Then I called the 800 number at exactly 8:00 AM on a Wednesday morning with my confirmation number from the online application. Having that reference number seemed to help - the agent could pull up my case immediately and we finished everything in about 20 minutes over the phone. The key documents I needed were: birth certificate, Social Security card, photo ID, and details about my current insurance coverage (including when it ends). Since you mentioned you have a marketplace plan ending when you turn 65, make sure to have those policy details handy - they'll want to coordinate the timing so there's no coverage gap. Don't stress too much about the deadline - you have until June since you're turning 65 in March. But definitely try that early morning call strategy with your online application reference number if you can get one started. Good luck!

I'm really sorry for your loss and can completely understand the anxiety around navigating survivor benefits during such a difficult time. The community has given you excellent advice - ESOP dividends absolutely will NOT count toward your Social Security earnings limit! I work as a financial advisor and deal with these questions regularly. The $22,560 earnings limit for 2025 only applies to wages from active employment and self-employment income - never to investment income like dividends, interest, or distributions from retirement accounts. Your ESOP dividends are classified as investment returns, not compensation for current services. When you apply next month, I'd suggest bringing copies of your ESOP statements that clearly show these are dividend distributions from your late husband's employer stock plan - this will help SSA process your application smoothly and avoid any potential confusion. Also, consider calling ahead to your local SSA office to schedule an appointment rather than just walking in - the wait times are usually much shorter with appointments. You're being very thorough by researching this beforehand, which will definitely pay off during the application process. Best of luck!

I'm so sorry for your loss and completely understand your concerns about navigating this process. As someone who went through a similar situation with my late spouse's retirement accounts, I can confirm what everyone else has said - ESOP dividends absolutely DO NOT count toward the Social Security earnings limit! The key distinction is that the $22,560 limit for 2025 only applies to "earned income" - meaning wages from active work or self-employment income. Your ESOP dividends are considered investment income, just like any other dividend or interest payment. When I applied for survivor benefits, the SSA representative specifically told me that pension distributions, 401k withdrawals, dividends, and other investment income don't count toward the earnings test at all. Just make sure when you apply that you clearly state these are ESOP dividend distributions from your late husband's employer plan (not wages or current employment income) and bring your monthly statements as documentation. This will help avoid any confusion during processing. You're being very smart to research this thoroughly beforehand - it will make the application process much smoother!

After reading through this whole discussion, I think you're in a good position to make an informed choice now. It's not a massive financial difference either way given that it's only 4 months. The earnings test complicates things slightly, but only for those 4 months. One last thing to consider: if you're truly miserable at work, what's the value of your happiness and mental health for those 4 months? Sometimes that's worth more than the financial calculation. Best of luck with your decision!

One thing I haven't seen mentioned yet is the "break-even" analysis. With a $58/month reduction on a $2,650 benefit, you'd collect about $2,592/month starting now versus $0 for 4 months then $2,650. It would take roughly 18-19 years for the higher benefit to make up for those 4 months of missed payments ($2,592 x 4 = $10,368). Given your good health and family longevity, this might actually favor waiting, especially with the part-time work earnings test issue. Have you considered gradually reducing your work hours over these 4 months to make the wait more bearable?

5 tries? You're LUCKY! I called 17 TIMES last month trying to fix my address change!!! And then they mailed my new card to the WRONG ADDRESS anyway!!! The whole system is BROKEN!!!!

I completely feel your frustration! I've been dealing with SSA for years helping my elderly parents navigate their benefits, and you're absolutely right - the MySocialSecurity portal is basically read-only. It's mind-boggling that in 2025 we can do almost everything online except communicate with one of the most important government agencies. For what it's worth, I've had better luck calling around 2-3 PM on weekdays - seems like there's a sweet spot after lunch when wait times are shorter. Also, if you're dealing with a benefit estimate discrepancy, sometimes it helps to have your most recent tax return handy when you call since they might need to verify earnings data. The whole system definitely needs a major overhaul!