Has anyone tried using TurboTax for this? I'm in the same situation and wondering if it automatically sorts out which SSN goes where.

I went through this exact same confusion last year! The key thing to remember is that when you're married filing jointly, you're essentially filing one combined return. Think of it this way: Schedule C and SE are like "individual worksheets" that need to match the specific person who received the 1099-NEC (so your wife's SSN goes there). But Schedules 1 and 2 are more like "summary sheets" that roll up into your main 1040 form - they should always use the primary taxpayer's SSN regardless of who earned the income being reported. I made the mistake of putting my husband's SSN on Schedule 1 the first time because all the income came from his freelance work, and the IRS sent us a letter asking for clarification. Once I corrected it to use my SSN (as the primary filer), everything processed smoothly. The IRS computer systems are looking for consistency across the return, not necessarily matching the SSN to who earned each specific dollar.

Hey! I'm new to this community and dealing with taxes for the first time too. Reading through all these responses has been really educational - I had no idea there were so many nuances to gambling winnings! Just wanted to say thanks to everyone who took the time to explain the difference between the technical requirements (all gambling income is taxable) versus the practical reality (IRS focuses on documented amounts over $600). It's helpful to see real experiences from people who've been in similar situations. One thing I'm taking away is that it's probably worth keeping better records going forward, even for small amounts, just to build good habits. And it sounds like there are some useful tools mentioned here that could help with tax questions as they come up. Thanks again for making this such a welcoming place to learn about these topics!

Welcome to the community and congrats on your first win! I can totally relate to the confusion - when I first started dealing with taxes, even small things like this seemed overwhelming. From what I've learned (and what everyone here has explained really well), you're in a pretty safe spot with that $20. The key takeaway is that while technically all gambling winnings are taxable, the IRS really focuses their attention on amounts where there's proper documentation - typically $600 and above where you'd receive tax forms. For your situation, you could go either way: report it as "other income" to be completely by-the-book, or just cash it and not worry about it since it's such a small, undocumented amount. Either choice is totally reasonable for a $20 win. The most important thing is that you're thinking about this stuff early! Building good tax habits now will serve you well if you ever hit bigger winnings down the road. And don't worry - we've all been beginners at this tax stuff at some point. The community here is really helpful for learning as you go!

I'm so sorry for your loss. Having gone through this process myself when my grandmother passed away, I completely understand how overwhelming it can feel to navigate all these tax requirements while grieving. You're absolutely correct to file Form 56 with the 1040 - attach it to the front of the return when mailing. One additional tip that really helped me: create a simple checklist of all the forms and documents you're including before sealing the envelope. I actually wrote on the outside of my mailing envelope "Final Tax Return for [Name] - Deceased [Date]" which helped ensure it got routed properly at the IRS. Since you mentioned using FreeTaxUSA, double-check that the software calculated any final year medical expenses correctly. Sometimes there are additional deductions available in the year of death that regular tax software doesn't automatically catch. Also, if your sister had any retirement account distributions or life insurance payouts, make sure those are handled appropriately on the return. Take care of yourself during this process - you're doing something really important and difficult, and it's okay to take breaks when you need them.

I'm so sorry for your loss. I went through this exact situation when my brother passed away last year, and I remember feeling completely overwhelmed by all the tax requirements on top of everything else. You're absolutely right to file Form 56 with the 1040 - definitely attach it to the front of the return when you mail it in. One thing that really helped me was making copies of everything before mailing. I kept a complete set of copies in a dedicated folder, which came in handy months later when I needed to reference some of the information for estate-related matters. Since your sister passed in August, make sure FreeTaxUSA is calculating the correct filing period (January 1 through her date of death). Also, if she had any bank accounts that earned interest after her death, that income would need to be reported on a separate estate return rather than her final personal return - but FreeTaxUSA should guide you through that distinction. One last tip: consider sending everything via certified mail with return receipt. It costs a little extra but gives you proof of delivery and peace of mind during an already stressful time. You're doing a wonderful thing by taking care of her final tax obligations so carefully.

5 Is the IRS Direct Pay website easy to use? My payment got returned last month and I still haven't gotten a notice, but I want to fix this ASAP.

Don't stress too much about this! I had the exact same thing happen to me last year - bank returned my payment because I forgot about an automatic bill that cleared the same day. The IRS will send you a notice in the mail (took about 2-3 weeks for mine to arrive), but you don't have to wait for it. You can go ahead and pay online right now through IRS Direct Pay. Just make sure to include a little extra for the returned payment penalty - it's usually around 2% of your original payment amount. The good news is this won't hurt your credit score or anything like that. It's really just a minor administrative issue that gets resolved once you pay. I paid mine the day after I got the notice and never heard anything else about it. One thing I learned: if this is your first time having payment issues with the IRS and you have a good payment history otherwise, you might be able to request "first-time penalty abatement" to get the penalty waived. Worth looking into!

Thanks everyone for all the detailed responses! This has been super educational. I had no idea about the direct donation requirement or the itemization issue. Based on what I'm reading here, it sounds like I can't deduct the 1-800-GOT-JUNK pickup, but I'm definitely going to look into those charity pickup services for future donations. The "donation bunching" strategy that Max mentioned is really interesting too - maybe I should plan my donations more strategically. One follow-up question: if I have items that are too worn for charity donation but still have some value, is there any tax benefit at all? Or is it just a loss either way? I'm thinking about some older electronics and appliances that work fine but have cosmetic issues.

Great question! Unfortunately, you cannot claim a tax deduction for items picked up by 1-800-GOT-JUNK, even if they eventually donate them to charity. The IRS requires that you donate directly to a qualified 501(c)(3) organization to claim any deduction - you can't use a middleman service. Here's what you need to know for future donations: - Donate directly to qualified charities like Goodwill, Salvation Army, or Habitat ReStore - Get proper documentation from the charity (written acknowledgment for donations over $250) - Items must be in "good used condition or better" - You can only deduct if you itemize deductions on Schedule A Since your furniture was in good condition, you might want to consider charity pickup services next time. Many legitimate charities offer free pickup and provide proper tax documentation. This way you'd get the same convenience as 1-800-GOT-JUNK but with the added benefit of a potential tax deduction. For your current situation, keep that receipt from 1-800-GOT-JUNK for your records, but unfortunately it won't help with your taxes.