I think I've already missed that window since it's been about 11 months since her passing, and as you mentioned, I've already completed the rollover into my 401K. I feel like I should have researched this better before making the initial decision, but I was dealing with a lot emotionally and just followed what the HR person at her company suggested.

That's understandable - these decisions often need to be made during difficult emotional times. Since the disclaimer option is no longer available, your best approach now is probably a combination strategy: First, designate her brother as the beneficiary for that portion of your 401K, ensuring he'll receive it if something happens to you. Then, work out a yearly gifting strategy once you're eligible for qualified distributions without penalties. You might also consult with an attorney about creating a simple agreement documenting your intentions, which could help clarify things for your own estate planning. Don't be too hard on yourself - you're trying to do the right thing in a system that doesn't make it easy.

This is actually not great advice. 401K loans become immediately due if you leave your job, and since OP is living overseas, that could be risky. Plus, if you can't repay the loan, it becomes a distribution with all the taxes and penalties. The gift tax concerns would still apply too.

Does Wave let you export reports that work for tax filing? That's been my biggest pain point.

Yes, you can export expense reports as PDFs or spreadsheets that work well for tax filing. The reports show all the transaction details and categories that match up with Schedule C. You can also generate specific date range reports, like quarterly or annual. The only limitation I've found is that the automatic categorization isn't always perfect, so I do have to go in and correct some entries occasionally. But for a free tool, it's pretty solid and has saved me tons of time compared to my old method of manually tracking everything in spreadsheets.

Oof that's rough. What app are you using now that has the cloud sync? I travel a lot for work and my biggest fear is losing all my trip receipts.

Do you remember what the monthly payment amount was for your $5,800 balance? I'm trying to figure out if they let you choose how much to pay each month or if they assign an amount.

You generally can choose your monthly payment amount as long as the debt will be paid off within the required timeframe. For amounts under $10,000, that timeframe is 3 years (36 months). So in my case, the minimum payment would have been about $161 per month not including interest and penalties. I actually opted to pay $200 per month to account for the ongoing interest and penalties and to clear the debt faster. They let me choose this amount during the application process. I set up direct debit from my checking account to avoid having to remember to make the payments and to get the lowest setup fee.

Completely agree about filing on time! The failure-to-file penalty is 5% of the unpaid taxes for each month your return is late, up to 25%. The failure-to-pay penalty is much lower at 0.5% per month.

Thank you for pointing this out! He did file on time, he just couldn't pay the full amount at once. I'll definitely suggest he try the online system since that seems to be the consensus here - much easier than trying to call again.

Omg you're right! I just double-checked my transcript and it's actually a 769 code, not 849. I totally misread it. Now I'm even more confused what that means. Is that better or worse than what I thought?

A 769 code typically indicates an earned income credit (EIC) claim on your return. This is just informational and shows the IRS has processed that part of your return. It's neither better nor worse than what you thought - it's just tracking different aspects of your return processing. What you should be looking for is either a 570 code (which would indicate a temporary hold) or an 846 code (which means your refund has been approved and issued). The 769 by itself just acknowledges your EIC claim was received and being processed. If you don't see a 570, that's actually good news - it means there's no specific hold on your account.

Tax Advocate Service is only accepting cases with real hardships now - like you're about to be evicted or have utilities shut off. They won't help with just checking refund status. They're super backlogged and turned me away when I called last week about my delayed refund.

12 Thanks for the suggestion! Would I need any special documentation to prove I actually tried to collect the debt? I have the original contract, all my invoices, and email threads showing I tried to get paid multiple times.

4 Yes, documentation is critical. Keep your original contract, all invoices sent, and especially any communications showing you attempted to collect payment. Also document how you determined the company was bankrupt and the debt uncollectible - like news articles about their shutdown, bankruptcy filings, or bounced emails to company addresses. Form 8949 is typically used for capital losses, but business bad debts can sometimes be reported as short-term capital losses. However, this really depends on your specific situation and whether you're using cash or accrual accounting.

3 Good point! They definitely should have issued a 1099-NEC for payments over $600. If they didn't, you should still report the income you actually received, but that missing 1099 might be another sign the company wasn't following proper business practices.