I'm actually going through this exact same situation right now! Got 1099s from both PrizePicks and Underdog showing about $2,800 in winnings, but when I add up all my losses from DraftKings, FanDuel, and a few other platforms, I'm probably down around $1,500 overall for the year. What's been helpful for me is creating a simple spreadsheet to track everything. I went through all my bank statements to find deposits to betting accounts, then logged into each platform to download whatever transaction history I could find. Most of the major sportsbooks have some kind of export feature, though they're all formatted differently. The tricky part is that even though I lost money overall, I still have to report those 1099 winnings as income and can only deduct my losses if I itemize. Since I rent and don't have a mortgage, my other itemizable deductions are pretty minimal, so I'm still trying to figure out if itemizing will actually benefit me. One thing I learned is that you really need to keep detailed records going forward - dates, amounts, outcomes for each bet. I wish I had started doing this from the beginning of the year instead of trying to piece everything together now. Definitely a lesson learned for next tax season!

I've been in this exact situation and it's definitely confusing at first! The key thing to understand is that you absolutely must report those 1099s from PrizePicks and Underdog - the IRS already has copies of those forms, so there's no way around it. Here's how it works: Your gambling winnings get reported as "Other Income" on your tax return, but your losses from DraftKings and FanDuel can only be deducted if you itemize deductions on Schedule A. The catch is you can only deduct gambling losses up to the amount of your gambling winnings - so if your 1099s show $3,000 but you lost $4,000 on other platforms, you can only deduct $3,000 of those losses. The documentation piece is crucial. I'd recommend logging into your DraftKings and FanDuel accounts right away to download your complete betting history for 2023. Most platforms have this available in their account settings or transaction history sections. If you can't find it online, contact their customer service to request annual statements. One important consideration: gambling losses are only beneficial if you itemize deductions, and your total itemized deductions need to exceed the standard deduction ($13,850 for single filers in 2023) to be worthwhile. Don't forget to include other potential deductions like state taxes, charitable donations, and mortgage interest when making this calculation. The good news is that all your sports betting activities are considered the same type of gambling for tax purposes, so your losses from different platforms can offset your winnings from others. Just make sure you keep detailed records in case of an audit!

You're absolutely right to be concerned about this EIN request during the audit. I went through something very similar with my late husband's trust audit two years ago, and the key is understanding the timing distinction. For the 2022 tax year when your mother-in-law was alive, if the trust properly qualified as a grantor trust, it should have been using her SSN - not an EIN. The IRS agent may be confused about the requirements or applying current post-death rules to the historical audit period. I'd recommend preparing a clear timeline showing: (1) During 2022, mother-in-law was alive and the trust was a grantor trust using her SSN, (2) After her death, the trust status changed and may now require an EIN going forward. These are two separate tax periods with different requirements. Consider requesting to speak with the agent's supervisor if they continue to insist on an EIN for the 2022 audit period. In my experience, supervisors tend to be more familiar with the nuanced grantor trust regulations. Also, document everything in writing - send a follow-up email after any phone conversations summarizing what was discussed and your position. The most important thing is not to let them pressure you into getting an EIN just to move the audit along if it wasn't required for that tax year. That could create unnecessary complications for future filings.

I went through a nearly identical situation with my mother's trust audit last year. The IRS agent initially insisted we needed an EIN for the audit period, but they were mixing up the pre-death and post-death requirements. Here's what worked for me: I prepared a simple one-page summary showing (1) the trust qualified as a grantor trust under IRC 671-679 during my mother's lifetime, (2) Treasury Regulation 1.671-4 specifically allows grantor trusts to use the grantor's SSN, and (3) the audit was for tax years when my mother was alive and the trust properly used her SSN. I also included copies of the relevant tax code sections and sent everything via email before our next call. The agent reviewed it with their supervisor and came back agreeing that no EIN was required for the audit period. The key is staying focused on the specific tax year being audited (2022) and not getting sidetracked by what might be required going forward now that your mother-in-law has passed. Those are completely separate issues with different rules. Don't let them pressure you into getting an EIN just to move things along if it wasn't required for 2022. Stand your ground with the regulations - you're likely correct about this.

OMG the offset system is wild! States can take $ for so many things: unpaid taxes (obv), child support, unemployment overpayments, student loans, court fees, toll violations, parking tickets, even unpaid utility bills in some states! And get this - some states share offset info w/ other states where you've lived. So your NY refund could be offset for a debt in CA. Crazy system that nobody explains to taxpayers until it's too late. SMH.

I feel your pain! This happened to me last year and the waiting period was torture. Here's what worked for me: Most states have a "Treasury Offset" or "Debt Collection" section on their revenue department website where you can search by SSN. Also try logging into your state's main tax portal - sometimes there's an "Account Summary" or "Notice History" section that shows recent actions before the physical letter arrives. If your state participates in the Federal Treasury Offset Program, you can also call 1-800-304-3107 for the automated hotline that tells you which agency requested the offset. Don't give up - the information is out there, it's just buried in government bureaucracy! 🙄

I'm confused about something - do I need to report my foreign account if I'm a US citizen but the money was earned and taxed in that foreign country? I have about $12,000 in a bank in Argentina where I work part time.

I was in a similar situation a few years ago with my UK account and completely understand the panic! Here's what I learned from going through this process: First, take a deep breath - you're not alone and there are solutions. Since your account has $38,000, you definitely need to file an FBAR for any year the balance exceeded $10,000. The good news is that the Streamlined Filing Compliance Procedures are specifically designed for situations like yours where the failure to report was non-willful. For the Streamlined Domestic Offshore Procedures (since you're living in the US), you'll need to file: - FBARs for the past 6 years (or however many years you've had the account if less) - Amended tax returns (Forms 1040X) for the past 3 years - Form 14653 (certification that your failure was non-willful) The key is being able to certify that your failure to report was non-willful - meaning you weren't intentionally hiding the account. Based on your post, it sounds like you simply weren't aware of the requirement, which would qualify. I'd strongly recommend consulting with a tax professional who specializes in international tax issues before proceeding. The penalties for willful non-compliance can be severe, but the streamlined procedures can eliminate or significantly reduce penalties for non-willful cases. Don't wait too long to address this - the sooner you get compliant, the better your position will be.

This is really helpful information! I'm in a similar boat - I've been doing freelance graphic design work and selling prints on Etsy, made about $3,200 this year. I had no idea about the $400 threshold for self-employment tax vs the $600 for 1099 forms - that's a crucial distinction that I think a lot of people get confused about. One thing I'm still unclear on though - when you mention deducting business expenses, do you need to have receipts for everything? I bought a lot of art supplies throughout the year but didn't always keep receipts for smaller purchases. Also, if I use my personal laptop for both design work and personal stuff, can I deduct a portion of that as a business expense? Thanks for breaking this down so clearly - definitely makes the whole process seem less overwhelming!

Just to add another perspective - I've been doing freelance illustration and selling handmade pottery for about 3 years now. The transition from regular W-2 employment to dealing with self-employment taxes was definitely a learning curve, but it's totally manageable once you get the hang of it. A few practical tips that helped me: - Set aside 25-30% of your side income in a separate savings account for taxes. This way you won't be scrambling to pay when tax time comes. - Use a simple spreadsheet or app to track income and expenses monthly - don't wait until the end of the year! - Take photos of all your receipts immediately and store them in a dedicated folder on your phone/cloud storage. The good news is that creative businesses often have lots of legitimate deductions that can significantly reduce your tax burden. Art supplies, craft materials, booth fees for markets, even business meals with clients - it all adds up. Just make sure everything is actually used for your business and keep good records. Don't let the tax stuff discourage you from pursuing your creative side income - it's really not as complicated as it seems at first!