This is a complex situation and I'd strongly recommend consulting with a tax professional who specializes in gambling taxation. With $520k in winnings and $595k in losses, you're dealing with significant amounts that will definitely draw IRS attention. A few key points to consider: - You'll need to report the full $520k in winnings as income - You can only deduct losses up to your winnings ($520k), so $75k in excess losses can't be deducted - You must itemize to claim gambling losses - make sure this makes sense vs. taking the standard deduction - Documentation is absolutely critical with these amounts The IRS scrutinizes large gambling loss deductions heavily. Make sure you have detailed session logs, casino statements, receipts, and can substantiate every dollar claimed. Consider getting a professional review of your documentation before filing to avoid potential audit issues down the road.

I've been through a similar situation with large gambling losses, and I can confirm everything others have said about the documentation requirements. The IRS is incredibly strict about this. One thing I haven't seen mentioned yet - if you're planning to claim these losses, you should also be prepared for the possibility that your return might be selected for additional review even before any formal audit. With $520k in gambling winnings reported, your return will likely get flagged for manual review during processing, which can delay your refund significantly. Also, make sure you understand the state tax implications in your state. Some states don't allow gambling loss deductions even if you can claim them federally, which could create an additional tax burden. Given the complexity and the amounts involved, I'd really recommend finding a CPA or tax attorney who has specific experience with gambling taxation. The general tax preparation places usually don't have the expertise to handle situations like this properly, and mistakes could be very costly with these dollar amounts.

22 I went through this exact situation last year with my survivor benefits. Just make sure you get your SSA-1099 form which shows all the benefits you received for the year. Social Security should mail it to you by January, but you can also get it online by creating an account on ssa.gov if you haven't received it.

I'm sorry for your loss. Losing a parent at such a young age is incredibly difficult, and it's admirable that you're taking responsibility for handling your taxes properly. To directly answer your question: Social Security survivor benefits may or may not be taxable depending on your total income, but they don't count toward the filing requirement threshold itself. However, since you earned $13,500 from your job and you're likely claimed as a dependent, you definitely need to file a return. Here's the key point many people miss: the filing requirement for dependents is based on *earned income* (like wages from your job), not total income including Social Security benefits. Since your earned income of $13,500 exceeds the dependent filing threshold of $1,350, you must file regardless of your Social Security benefits. As for the benefits themselves, with your income level, it's very likely that none of your $7,800 in survivor benefits will be taxable. But you still need to report them on your return - they go on lines 6a and 6b of Form 1040, with the help of the Social Security Benefits Worksheet in the instructions. Don't stress too much about this - you're actually in a pretty straightforward situation, and you'll likely get a refund of taxes withheld from your paychecks!

I was in almost the exact same situation as you last year - got my first 1099-K from Vinted for $712 in sales and had no idea what to do with it! I was so worried I'd messed up somehow by not tracking everything from the beginning. The good news is that since you're selling personal clothes for less than you originally paid, you probably won't owe much (if any) tax on this. The 1099-K just shows gross payments - it doesn't account for what you originally spent on those clothes or any of the selling expenses. Here's what helped me get organized: I went through my Depop sales history and made a list of everything I sold. For each item, I estimated what I originally paid based on the store tags if I still had them, or by looking up similar items at stores where I typically shop. Don't stress about being perfectly accurate - reasonable estimates based on your shopping habits are totally acceptable. Then I added up all my expenses: Depop's selling fees, PayPal transaction fees, shipping costs, even the cost of mailers or packaging supplies. These are all deductible business expenses that reduce your taxable income. Most people in your situation end up with very little actual profit once you subtract the original cost of items and all the fees. The key is just reporting it properly on Schedule C so the IRS can match your return to the 1099-K they received. You've got this!

Don't worry - you're definitely not alone in this situation! I got my first 1099-K from PayPal last year for around $680 in sales from decluttering my apartment on Facebook Marketplace and OfferUp. Like you, I was completely overwhelmed at first. The most important thing to understand is that the 1099-K amount is NOT your taxable income - it's just the gross payments you received. Your actual taxable income (if any) is what's left after you subtract what you originally paid for those items and any selling expenses. Since you mentioned these were personal clothes you sold for less than you originally paid, you'll likely end up with little to no taxable income once you properly account for everything. Here's my simplified approach that worked well: 1. List each item you sold and your best estimate of what you originally paid for it 2. Add up all your selling expenses (Depop fees, PayPal fees, shipping costs, packaging materials) 3. Subtract both of these from your gross sales - that's your actual taxable profit For estimating original costs on clothes you've had for a while, I just looked at where I typically shop and what similar items cost there now, then adjusted slightly for when I bought them. The IRS accepts reasonable estimates for personal property when you don't have exact receipts. You'll report this on Schedule C, but don't let that scare you - it's pretty straightforward once you have your numbers organized. Being only $43 over the threshold actually works in your favor since it shows this was clearly just casual selling, not a business operation.

Just to give a different perspective - I tried doing my S-Corp taxes with TurboTax Business last year and deeply regretted it. Spent 20+ hours struggling through it, thought I'd done everything right, and still got notices from the IRS about missing forms 6 months later. Had to hire a CPA to fix everything anyway and ended up paying way more than if I'd just gone to them in the first place.

As someone who's been through the exact same transition from W-2 to S-Corp, I'd definitely recommend going the CPA route for your first year. The complexity isn't just in filing the returns - it's understanding all the ongoing compliance requirements that TurboTax won't teach you. Since you mentioned you've only been taking owner's draws instead of paying yourself a salary, you're going to need professional help to sort that out anyway. The IRS is pretty strict about S-Corp owners paying themselves reasonable compensation through payroll, and getting that wrong can trigger audits or penalties. One thing I wish someone had told me: start interviewing CPAs now, not in March when everyone's swamped. Many good ones are already booking up for tax season. Look for someone who specializes in small business and can explain things clearly - you want to learn the process, not just hand everything off blindly. The investment in professional guidance your first year will save you headaches (and probably money) down the road. Once you understand the S-Corp requirements and have proper systems in place, you can always consider doing simpler years yourself later.

This is absolutely infuriating and I'm so sorry you're dealing with this. Your employer is essentially stealing from you - they're pocketing the difference between what they actually paid you and what they reported, plus they're likely avoiding paying their share of employment taxes on your real wages. The $6,000 difference between your W2 and IRS transcript is massive and definitely not a simple accounting error. This is deliberate fraud. I'd recommend acting quickly before they have a chance to cover their tracks or alter any records. Beyond filing the forms others have mentioned, you might also want to check if any of your coworkers are experiencing the same thing. Employers who do this to one person usually do it to multiple employees. If you can find others who've been affected, it strengthens the case when you report it. Also, make sure you're calculating the full impact - you're not just missing out on the underreported wages, but potentially missing Social Security credits, unemployment benefit calculations, and other benefits tied to your reported income. This affects way more than just your current tax return. Stay strong and don't let them intimidate you. What they're doing is criminal and you have every right to report it.

This is a textbook case of payroll fraud and you absolutely need to take action. The $5,500+ discrepancy between your W2 and IRS transcript isn't a mistake - your employer is deliberately underreporting your wages, which means they're stealing from both you and the government. Here's what you should do immediately: 1. File Form 4852 (Substitute W-2) with your tax return using the correct wage amounts from your IRS transcript 2. Report the fraud using Form 3949-A to alert the IRS to investigate your employer 3. Keep copies of everything - your pay stubs, bank records, the fraudulent W2, and your IRS transcript Don't worry about retaliation - there are federal whistleblower protections that make it illegal for employers to fire you for reporting tax violations. And honestly, do you really want to keep working for someone who's been stealing from you for over a year? This isn't just about your current taxes either. The underreporting affects your Social Security earnings record, unemployment benefits eligibility, and other programs based on reported income. You need to fix this now before it gets worse. Your employer is banking on you being too scared or confused to report them. Don't let them get away with it. You deserve every penny they've stolen from you.