UPDATE: I was able to get my SSA-1099! The Claimyr service actually worked - got through to an agent in about 10 minutes. They confirmed my identity and helped me reset my online account access. I just printed my form and can now finish my taxes. Thanks everyone for the help!

Glad to see this got resolved! For anyone else reading this thread, just want to add that if you're having trouble accessing your my Social Security account, you can also request a new SSA-1099 by mail by calling the automated phone system at 1-800-772-1213 and following the prompts (no need to speak to an agent). It usually takes 7-10 business days to arrive, so plan accordingly if you're close to tax deadlines. The online method is definitely fastest when it works though!

congrats on retirement!! enjoy it :

Just wanted to add one more thing that might be helpful - make sure to keep good records of that vacation payout for your tax preparer next year! Since it's such a large amount, having documentation showing it was accumulated vacation time (not regular wages) might be useful when filing your taxes. Some tax preparers like to see the breakdown between regular final pay and vacation/sick leave payouts. Congratulations on your retirement - sounds like you've planned this out well!

I don't think anybody mentioned this yet, but you should also check if starting your Social Security affects any health insurance you might have through your employer while on medical leave. That was a nasty surprise for my sister when she did something similar!

Just wanted to add another perspective - I was in a very similar situation 2 years ago at age 66. I was on paid medical leave after knee surgery and decided to file for SS retirement benefits. The key thing that helped me was getting everything in writing from my employer's benefits department. I asked them to confirm in an email: 1) Whether my PML would continue if I filed for SS, 2) How the PML would be reported for tax purposes, and 3) Whether there were any plan provisions that would offset my PML if I received SS benefits. Having it documented protected me later when there was some confusion in payroll. Everything worked out fine - I got both benefits until my PML expired, then transitioned to full retirement. The peace of mind from having clear written confirmation was worth the extra step!

I'm sorry for your loss. Yes, survivor benefits absolutely do receive annual COLA increases just like regular retirement benefits. Once you start receiving them, your benefit amount will adjust each January with the cost-of-living increase announced by SSA the previous October. One thing to keep in mind - you mentioned you'll be eligible at 60, but claiming at that age will permanently reduce your survivor benefit to about 71.5% of your husband's full benefit amount. The reduction is permanent, but the COLA increases will still apply to whatever reduced amount you receive. Since you have your own work record, definitely consider getting benefit estimates for both your survivor benefit and your own retirement benefit at different claiming ages. You might benefit from a "claim and switch" strategy - taking one benefit early and switching to the other later when it reaches its maximum value. This can help maximize your lifetime Social Security income. The SSA website has a benefit estimator tool, but given the complexity of your situation, it might be worth scheduling an appointment with your local SSA office to discuss your specific options.

I'm sorry for your loss, Oliver. This is such a difficult time to be dealing with these complex benefit questions. Yes, survivor benefits do receive annual COLA increases just like all other Social Security benefits. Once you start receiving them, your monthly payment will increase each January based on the cost-of-living adjustment that Social Security announces in October. One thing I want to add that might help with your budgeting - you can actually create a my Social Security account online at ssa.gov to get benefit estimates for both your own retirement benefit and your potential survivor benefit at different claiming ages. This can help you see the actual dollar amounts you'd be working with under different scenarios. Also, since you mentioned having trouble reaching SSA by phone, you might try calling first thing in the morning (8 AM) or late in the afternoon after 4 PM - those tend to be less busy times. Another option is to visit your local Social Security office in person, though you'll want to arrive early since they often have limited walk-in hours. The claiming strategy others mentioned is really important in your situation. With 30 years of full-time work, you likely have a decent benefit of your own, so running the numbers on when to claim each benefit could make a significant difference in your total lifetime benefits. Take care of yourself during this difficult time, and don't hesitate to seek help from family or friends when navigating all these decisions.

Another thing to keep in mind - if you received a large backpay amount, you might want to consider making quarterly estimated tax payments for next year to avoid another surprise tax bill. Since SSDI doesn't automatically withhold taxes like regular employment, many people get caught off guard. You can set up voluntary withholding from your monthly SSDI payments by filling out Form W-4V, or make quarterly payments directly to the IRS. I learned this the hard way after my first year of benefits!

Looking at all the helpful advice here, I wanted to add something that might help with the immediate concern about owing a large tax bill. If you do end up owing more than you can pay when you file, the IRS has several payment options available. You can set up an installment agreement online through their website, and if you owe less than $50,000, you can often get approved automatically for a payment plan. Also, don't panic if the tax calculation seems overwhelming - many tax software programs like TurboTax and H&R Block have specific sections for Social Security benefits and can walk you through the lump-sum election calculation. That said, given the amount of your backpay ($31,500), it's probably still worth investing in a tax professional who specializes in Social Security taxation, especially for this first year. They can make sure you're taking advantage of all available strategies to minimize your tax burden.