I'm dealing with a very similar situation but with a different twist - I won $650 from FanDuel but it was spread across multiple small wins over a few months rather than one big bet. I never received any tax forms either. From all the great advice here, it sounds like I still need to report the full amount regardless of how I won it or whether I got forms. My question is: should I report this as one lump sum of $650 in gambling winnings, or do I need to break it down by each individual winning bet? I can access my FanDuel account and see the transaction history, but there were probably 8-10 different winning bets ranging from $25 to $180 each. For TurboTax purposes, I'm assuming I just enter the total amount as gambling winnings from FanDuel, but wanted to double-check since my situation is a bit different from the original poster's single big win. Also, I had some losing bets too during that same period - probably lost about $400 total. Based on what others mentioned about needing to itemize to claim gambling losses, it doesn't sound like it would be worth it for me since I'd be taking the standard deduction anyway. Just wanted to confirm that's the right approach. Thanks for all the helpful information in this thread - it's exactly what I needed to figure out how to handle this properly!

I work as a tax preparer and see this exact situation all the time, especially with sports betting becoming more popular. You're absolutely doing the right thing by wanting to report this income! Since you won $800 from a single bet, FanDuel wasn't required to send you a W-2G (which is typically for winnings of $1,200+ from slot machines or $5,000+ from poker). However, you're still legally required to report ALL gambling winnings as income. In TurboTax, go to the "Income" section and look for "Less Common Income" or "Additional Income Sources." Select "Gambling, Lottery, and Prize Winnings." There should be an option like "I don't have a tax form" or "Enter without a form." You'll just need to enter: - Payer: FanDuel - Amount: $800 - Type: Sports betting winnings Keep your bank statement showing the deposit from FanDuel as documentation. If you can still access your FanDuel account, screenshot your transaction history showing the winning bet and withdrawal - this creates a nice paper trail in case you're ever audited. The IRS actually prefers taxpayers who proactively report income without forms rather than those who try to hide it. You're showing good faith compliance with tax law, which is always the right approach. Don't worry about getting "flagged" - millions of people report gambling winnings this way every year!

Quick tip from someone who's been freelancing for 15+ years: start including a damage clause in your contracts! I specifically have language that states any reimbursements for damaged equipment are not considered income and will not be reported on tax forms. It's saved me from this exact headache multiple times. Most clients don't even notice it when signing, but it gives you something concrete to point to when their accounting department tries to 1099 you for reimbursements. Worth adding to your contracts going forward!

This is a great discussion with solid advice from everyone! I'm dealing with a similar situation right now where a client damaged some lighting equipment during a corporate shoot. Reading through all these responses really helped clarify my options. I'm definitely going to try contacting their accounting department first to explain that it should be treated as property damage reimbursement, not service income. If that doesn't work, the backup plan of reporting it as income but then deducting the exact repair amount on Schedule C makes sense as a safety net. The contract clause suggestion from Kelsey is brilliant - I'm definitely adding that to my standard agreement going forward. Prevention is always better than having to fix these issues after the fact! Thanks to everyone who shared their experiences and solutions. This community is incredibly helpful for navigating these tricky tax situations that come up in freelance work.

i messed this up last year and got audited!!! make sure ur using cash accounting not accrual. sounds like u want cash method so u can deduct when u pay not when u get the stuff. my tax guy says most of us freelancers use cash method anyway its easier

This is a great question that trips up a lot of freelancers! Since you're filing Schedule C as an independent contractor, you're almost certainly using the cash method of accounting (unless you specifically elected accrual method with the IRS, which is rare for freelancers). With cash method accounting, you deduct business expenses in the tax year you actually make the payment, not when you receive the goods or services. So in your case, if you take the equipment home this weekend but don't pay until January/February 2025, you would claim this $2,800 deduction on your 2025 tax return. Just make sure to keep detailed records of: - The purchase agreement showing the buy-now-pay-later terms - When you actually received the equipment - All payment receipts when you start making payments in 2025 This timing strategy is perfectly legitimate and sounds like it aligns well with your tax planning goals. The key is being consistent with your accounting method and having good documentation to support the timing of your payments.

I actually went through this exact situation two years ago and can confirm that yes, you'll absolutely still get credit for all the taxes that have already been withheld this year. The IRS doesn't care about the timing of when taxes were withheld - they just look at your total annual income versus total withholding when you file. One thing that really helped me was calculating my "breakeven point." I looked at what I'd already had withheld, estimated my total tax liability for the year, and figured out exactly how much I needed to set aside from each remaining paycheck. This prevented both overpaying and underpaying. Also, don't forget to submit a new W-4 to your employer to make the change official. Some people think they can just tell payroll verbally, but you need the paperwork on file. And if you're married or have dependents, double-check that going exempt won't mess up any credits you're planning to claim - sometimes having zero withholding can affect things like the Child Tax Credit advance payments if you're receiving those. The financial discipline aspect you mentioned is key. I found it helpful to treat my "tax savings" like any other bill - set up automatic transfers so the money never feels like it's available to spend.

I went through this exact same decision process last year and can share what I learned! Yes, you'll definitely still get credit for all the taxes already withheld - the IRS treats your annual tax return as a reconciliation of total income vs total withholding for the entire year, regardless of when those withholdings occurred. A few practical tips that made the transition smoother for me: 1. **Calculate your effective tax rate first** - Look at last year's return and divide your total tax by your total income. This gives you a baseline percentage to save from each paycheck. 2. **Account for timing** - Since you're switching mid-year, calculate how much you've already paid versus how much you'll owe, then divide the remaining amount by your remaining paychecks. 3. **Set up separate savings immediately** - I opened a high-yield savings account specifically for taxes and automated transfers. The interest you earn on that money is a nice bonus compared to giving the IRS an interest-free loan. 4. **Review quarterly** - I checked my progress every 3 months using tax software to make sure I was still on track, especially important if you get bonuses or overtime. The peace of mind from having more control over your cash flow is worth it, but definitely respect the discipline required. Make sure that automatic savings transfer happens before you get used to seeing the bigger paychecks!

I'm dealing with a very similar situation right now with a failed tech startup LLC. Based on what I've learned from my research and conversations with tax professionals, here are a few key points that might help: First, the timing matters a lot. You generally have 3 years from when you filed your original return to claim a refund via amended returns, but there's an exception for worthless securities that extends this to 7 years from the original due date. This could be crucial for your situation since it's been several years. Second, you'll want to establish the exact year the investment became worthless. This isn't necessarily when the company officially closed, but when it became clear there was no reasonable prospect of recovery. Based on your description, this sounds like it happened when the managing partners abandoned the company. Third, gather any evidence you can find that shows you made reasonable efforts to get information or recover your investment. Emails to the managing partners, attempts to contact the registered agent, anything that shows you tried to determine the status of your investment before claiming it as worthless. The fact that another investor successfully claimed these losses is encouraging - it shows there's precedent for your situation. I'd strongly recommend finding an accountant or tax attorney who has experience with partnership abandonments rather than trying to handle this with someone who isn't familiar with these specific rules. Also document everything thoroughly because the IRS may have questions about why you're claiming losses without K-1s, especially if it triggers any audit flags.

I'm sorry to hear about your situation - it's frustrating when you trust your accountant to handle something this important and they just ignore it. You're definitely not alone in this type of mess. Based on what others have shared here, it sounds like you have several viable options for claiming these losses even without K-1s. The key seems to be treating this as an "abandonment loss" since there's clearly no one left to manage the LLC or generate proper tax documents. From what I'm reading, you'll want to: 1. Gather all your original investment documentation (bank statements, operating agreements, any old K-1s) 2. Document your attempts to get information from the defunct company 3. Calculate your tax basis (what you invested minus any prior losses claimed) 4. File amended returns for the appropriate tax years The timing aspect that others mentioned is crucial - you need to determine exactly which tax year the investment became worthless. This sounds like it happened when the managing partners abandoned the company, not necessarily when it was legally dissolved. I'd strongly recommend finding a new accountant who actually has experience with partnership abandonments. Your current one clearly isn't equipped to handle this situation. The fact that another investor successfully claimed similar losses shows this is definitely doable with the right expertise. Don't let this drag on any longer - you've already lost several years of potential tax benefits because of your accountant's negligence.