This reminds me of when I retired. I think what's happening is the monthly test vs. annual test confusion. When you first retire, you get to use the monthly test which is definitely better for people who work part of the year then stop completely.

I just called SSA again using that Claimyr service someone mentioned (it actually worked!), and got through to a very knowledgeable agent. She confirmed I can absolutely start benefits in December for January payment using the monthly earnings test since I haven't worked since July. She also said I could technically apply for benefits going back to August (first payment in September) if I wanted to, but I'd need to specifically request retroactive payments for those months. I'm going to start with December/January payment as originally planned. Thanks everyone for helping clear this up! The monthly earnings test vs. annual test distinction was the key piece I was missing.

To directly answer your original question: The WEP applies when you receive a pension based on work where you didn't pay Social Security taxes. The key factor is not whether you receive monthly payments or a lump sum, but whether the payment is based on non-covered employment. An important exception exists if your pension is based on a mix of covered and non-covered employment. If that's the case, the SSA will only apply WEP to the portion derived from earnings where you didn't pay Social Security taxes. Request a detailed WEP calculation from SSA before making your decision.

Another consideration: depending on your age and specific situation, you might want to look into whether the "substantial earnings test" might help reduce your WEP impact. If you can demonstrate that you had substantial earnings under Social Security for enough years (the magic number is 30, but there's a sliding scale), your WEP reduction can be lessened or eliminated. This would be true whether you take the pension as a lump sum or monthly payments.

Just to add one more important point: If you've just started collecting Social Security in November 2024, your benefit amount might be different in 2025 due to the annual Cost of Living Adjustment (COLA). This adjustment took effect with December 2024 benefits (payable in January 2025). Make sure to budget accordingly for any tax implications based on your new benefit amount going forward.

Thank you everyone for all the helpful answers! I'll keep an eye out for the SSA-1099 in the mail, but I'm also going to set up my online account to access it there if needed. Since I'm past FRA, it sounds like I don't need to worry about the earnings limit, which is a relief. I'll look into that W-4V form to have some taxes withheld from my SS benefits going forward to avoid a surprise tax bill. This community has been incredibly helpful!

Something NO ONE has mentioned yet is that sometimes SSA will send you a letter saying what month your benefits officially start - keep this letter!!! You might need it to prove when you were entitled to benefits vs when you actually got paid. Especially if there's ever an audit or question later.

Just to add one more point of clarification - when the backpay arrives, the SSA-1099 will show the total amount paid to you during that calendar year. It won't specify which months the payments were for, just the total received. This is why it's important to keep your award letter that explains the breakdown of payments. Also, since you're asking about taxes, remember that depending on your combined income (adjusted gross income + nontaxable interest + half of SS benefits), up to 85% of your Social Security benefits may be taxable. Since you're still working, this is something to be aware of for your tax planning.

I thought I read somewhere that Congress might eliminate WEP? Is that true or just wishful thinking?

Update: I found the WEP calculator link and it worked! For anyone else dealing with this, it shows both the regular PIA and the reduced amount after WEP. In my case, my monthly benefit would be $2,285 without WEP but will be $1,786 with the reduction. My 23 years of substantial earnings helped reduce the penalty from the maximum, so that's good news at least. Thanks everyone for your help!