My brother is a contractor and I can tell you exactly what's happening here. They're probably reporting much less income than they actually make, and 1099s make that harder to do. That's why they're pushing back so hard. Send a final written notice (certified mail) stating that you'll be filing the 1099s for the full amount as legally required, whether or not they provide W-9s. Include IRS Form W-9 and a prepaid return envelope. State clearly that failure to provide the information may result in them being subject to backup withholding on future payments. Keep copies of everything. If they still don't provide the W-9s, file the 1099s with whatever information you have (name, address, etc.) and indicate they refused to provide their taxpayer ID. The IRS will handle it from there.

Wait, I'm confused about something - I have a rental property and pay people for repairs all the time. Am I supposed to be collecting W-9s from everyone? Like even the guy who mows the lawn for $50 a week? This is the first I'm hearing about this requirement...

9 Tax preparer here. Just to add some clarity: The "under $600" confusion is one of the most common issues I see with clients. The $600 threshold only determines whether the PAYER must issue a 1099 form. It has absolutely nothing to do with whether YOU must report the income. All income from any source is legally required to be reported on your tax return, even if it's $5. The IRS computer matching system will catch discrepancies between what's reported by others using your SSN and what you report on your return, regardless of amount.

4 Does anyone know if this applies to stuff sold on Facebook Marketplace too? I sold some old furniture and made maybe $400 total last year. No 1099 forms or anything, just cash and Venmo. Do I seriously need to report that??

lmao good luck understanding that mess. I stared at mine for hours and gave up 🤮

Look for these key codes on your transcript: 150 means they received your return, 570 is a hold (could be for review or missing info), and 846 is the golden one - that's your DDD! The date next to 846 is when your refund gets deposited. If you only see 570 with no 971 notice code, it might just be a routine review. Check back in a few days - transcripts usually update overnight between Tuesday-Friday.

Everyone's talking about the tax benefits, but don't forget about stimulus checks or recovery rebates! If there's another round of those in 2025 for the 2024 tax year (you never know!), having extra dependents could mean more stimulus money. During the last rounds, it was an extra $1400-$1600 per dependent. This is separate from the regular tax benefits and something to consider if you legitimately qualify to claim them. Just make sure you're eligible first - as others said, the living situation makes this complicated.

The key thing everyone's missing here is that your mom not filing taxes doesn't automatically make you eligible to claim your brothers. The IRS looks at who actually has the right to claim them based on the dependency tests, not who chooses to file. Since your brothers don't live with you, you'd need to meet the "qualifying relative" test, which means providing more than 50% of their total support AND they can't be claimed by anyone else who has a stronger claim (like your mom). Even if your mom doesn't file, she still technically has the stronger claim as their parent and primary caregiver. Your $800-1000 monthly support might be substantial, but you'd need to prove it covers more than half of ALL their expenses - housing, food, medical, clothing, education, etc. The IRS will want detailed records showing exactly what your money paid for. My advice: before doing anything, calculate the total cost of supporting your brothers for the year (including the value of housing your mom provides) and see if your contributions truly exceed 50%. If not, you don't qualify regardless of whether your mom files. If yes, get Form 8332 signed by your mom and keep meticulous records of every expense your money covers. Given the audit risk mentioned by others, this might be a situation where paying a tax professional for guidance upfront is worth it to avoid potential penalties later.

Another tip - when you submit multiple Form 8889s, write "HSA 1 of 3", "HSA 2 of 3", and "HSA 3 of 3" at the top of each form. This helps the IRS understand that you're submitting multiple forms intentionally and they're all part of the same tax filing. I had a similar situation and this simple labeling prevented confusion. The IRS agent I spoke with specifically recommended this approach!

Just labeling the forms is usually sufficient! I didn't include any additional explanation letter when I submitted my multiple HSA forms, and the IRS processed them without any issues. The numbering system (like "HSA 1 of 3") makes it clear that you're intentionally filing multiple forms for the same tax year. However, if your situation is particularly complex or if you're responding to a specific IRS notice, you might want to include a brief cover letter explaining that you're filing separate Form 8889s for each HSA account. But for most cases, the labeling alone should do the trick. The key is making sure each form is complete and accurate for its specific HSA, with the correct distributions and qualified medical expenses allocated appropriately across all forms.