Has anyone actually tried to report a loss on line 2 of 8995-A using the Free Fillable Forms? I tried entering the negative number with a minus sign and it worked fine for me. Maybe try "-24000" instead of "(24000)" for the format?

Thanks everyone for all the helpful responses! I just tried entering my loss as "-24000" on the Free Fillable Forms and it worked perfectly. I must have been doing something wrong with the formatting before. To summarize what I learned from this thread: I definitely need to include both LLCs on Form 8995-A, with my profitable one showing $273k and the loss one as -$24k, giving me a net QBI of $249k for the deduction calculation. Since neither business is a specified service trade or business, I should be good to go. Really appreciate everyone taking the time to explain this - especially the clarification that losses from one qualified business must offset income from another. This makes total sense now, and I feel much more confident about getting this right on my return.

As someone who works as a tax preparer, PLEASE DO NOT try to claim your girlfriend. Her income is too high anyway, but more importantly, attempting to claim someone who's legally married to someone else is a huge red flag. I've seen the IRS come after people for less. Just file Head of Household with your son as your dependent, take the child tax credit if he qualifies, and leave your girlfriend's tax situation separate.

I'm going through a similar situation with my partner who's been separated for years but not legally divorced. After reading through all these responses, it sounds like your girlfriend's income of $11,000 would disqualify her anyway since the limit for qualifying relatives is around $5,000. Even if her income was lower, the marriage complication makes this risky. I'd definitely recommend following the advice about just filing Head of Household with your son - that's already a significant tax advantage compared to filing single, and you'll get the child tax credit too. If you really want a definitive answer about your specific situation, it might be worth using one of those services mentioned to get through to an actual IRS agent. But honestly, it sounds like the safest and most beneficial approach is to keep things simple and just claim your son while filing HOH. The tax savings from that status change alone should be substantial.

Another thing worth considering - if you expect your 2025 income to be significantly different from 2024 (like getting a big raise, changing jobs, etc.), that might impact WHEN you want to recognize the interest income. Interest is taxed at your ordinary income rate. So if you expect to be in a lower tax bracket in 2024 than 2025, getting that interest in 2024 might save you some money. Conversely, if you expect 2025 to be a lower income year, maybe waiting makes sense.

Great question! I've been dealing with HYSA taxation for a few years now and wanted to add one more practical tip that helped me a lot. Keep detailed records of when you make deposits and any promotional bonuses you might receive. Some banks offer signup bonuses for new HYSA accounts (like $200 for depositing $10k+), and these bonuses are also taxable income in the year you receive them - they'll show up on a separate 1099-MISC form. Also, if you're comparing rates between banks, don't forget to factor in any monthly fees or minimum balance requirements. A 4.8% APY with no fees might actually be better than 5.0% APY with a $15 monthly fee, especially on your $13,500 balance. One last thing - set up automatic transfers if your bank allows it. The compounding effect of consistent deposits plus that 5% rate will really add up over time, and you won't have to think about the timing as much. Just make sure you understand your bank's specific interest payment schedule so you can plan for tax time!

Your safest bet is to just follow IRS instructions exactly. Use your SSN for W-9s if you're a single-member LLC taxed as a sole proprietorship. Period. If you've been using your EIN incorrectly, contact those clients and send them updated W-9s with your SSN. It's better to fix it now than deal with notices and potential penalties later.

I went through this exact same confusion last year! As a single-member LLC owner myself, I initially made the same mistake of using my EIN on W-9s because it seemed more "professional." Here's what I learned after consulting with my CPA: Yes, you should use your SSN, not your LLC's EIN, on W-9 forms if you're taxed as a sole proprietorship. The IRS instructions are correct, even though it feels counterintuitive. The key thing to understand is that your LLC provides liability protection (which is huge!), but for tax purposes, it's "disregarded" - meaning the IRS treats your business income as if it flows directly to you personally. Don't panic about the W-9s you've already submitted with your EIN. I had the same situation and my CPA said it's actually pretty common. The important thing is that you report all that income on your Schedule C. You might get a notice from the IRS asking to match up the numbers, but as long as you've reported everything correctly, it's usually just a matter of explaining that your LLC is a disregarded entity. Going forward, I'd recommend using your SSN on new W-9s to stay compliant with IRS instructions. If privacy is a major concern, you could explore electing S-Corp status, but that comes with its own complexities and costs that might not be worth it depending on your income level.

Quick question - do I face the same issue with multiple brokerage accounts? I have accounts with Fidelity, Robinhood and Webull, and only received 1099s from Fidelity so far.

Hey Romeo, I totally understand your stress about this! I went through something similar last year. Here's what I learned: First, check if your investment platform has a minimum threshold for issuing 1099s. Some smaller platforms only issue them if you have $10+ in dividends or $600+ in other income. With $750 in total trades, you might fall below their threshold. However, you're still legally required to report all investment income and losses regardless of whether you receive a 1099. The good news is that if you lost money overall, those losses can actually help reduce your tax burden! Here's my suggestion: Download your complete transaction history from the platform (this is usually available even if 1099s aren't). You'll need the purchase date, sale date, purchase price, and sale price for each transaction. Then you can either: 1. Use tax software that can import trading data 2. Manually fill out Form 8949 and Schedule D 3. Use one of the specialized tax tools mentioned above Don't panic about the deadline - you can always file an extension if needed. The most important thing is to report accurately, even if it means using your transaction history instead of waiting for a 1099 that might not even be coming. You've got this! The $200 loss you mentioned can actually offset other income, so it's worth documenting properly.