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Old tax debt from $55K ballooned to $190K in 10 years - what are my options now?

So about 10 years ago I had a business that was doing pretty well. Made enough to rack up about $65K in taxes for one year - roughly $53K federal and $12K state. Then the business started struggling. I made the risky choice of using tax money I owed (all 1099 self-employment taxes) to try keeping the business afloat rather than just paying the tax bill and closing up. Well, that gamble didn't work out, and I've been carrying this tax burden for over a decade now. Currently, I'm looking at owing around $85K to the feds, but what's crazy is the state is claiming I owe something like $135K... which seems impossible based on the original amount. I basically buried my head in the sand all this time. I did try talking to the IRS about 3 years after everything fell apart to set up payments, but they wanted $2,500 monthly when I wasn't even bringing in that much personally. They told me to just pay what I could, but I'd heard about this '10-year statute of limitations' where they only have a decade to collect before it becomes uncollectable. So I figured waiting it out was my best option. But here we are 10 years later, and I'm not sure where I stand. Seems weird to call the IRS like "hey it's been 10 years, are we good now?" During this time, I've scraped by (still filed and paid my current year taxes), but never touched that huge old bill. I can't keep any real money in bank accounts because tax liens occasionally hit and clean me out. They've done this twice, both times getting less than $120. They haven't hit me again recently, probably because they know there's nothing there. I'm tired of living like this. I either want to know how much longer this cloud hangs over me, or find a solution to settle and move forward. I've heard about offers in compromise, but I'm basically broke. I can't magically produce $25-35K for a settlement offer. My credit is destroyed. The only positive is I've got another business starting to gain traction, and I want to resolve this old mess so I can move forward properly. Any advice on what path I should take? Can't afford a tax attorney right now. Just looking for guidance on possible resolution options that I can research further. Thanks for any help!

Have you considered bankruptcy? Tax debts CAN sometimes be discharged in bankruptcy contrary to what most people think. If the taxes are more than 3 years old, you filed the returns more than 2 years ago, and the taxes were assessed more than 240 days ago, they might be eligible for discharge in Chapter 7. Even if they can't be discharged, Chapter 13 bankruptcy could force both the IRS and state into a reasonable payment plan based on what you can actually afford.

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This is actually not entirely accurate. While some taxes can be discharged in bankruptcy, there are strict requirements. Self-employment taxes specifically have additional complications because they include both income tax and what would normally be FICA taxes (Social Security and Medicare). The FICA portion is much harder to discharge. Also, filing fraudulent returns or willful evasion will prevent discharge regardless of timing. Given that OP deliberately chose not to pay the taxes to fund their business instead, a bankruptcy judge might view that as willful evasion.

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I worked for a state tax agency for 8 years. Here's what's happening with your state tax bill: most states have much higher penalty and interest rates than the IRS, and many states (unlike the IRS) compound interest. This is why your state bill has grown more dramatically. For state taxes, I'd recommend requesting a penalty abatement first. Many states have first-time abatement programs similar to the IRS, and some even have hardship programs if you've been in difficult financial circumstances. Don't assume the 10-year rule applies to your state. Some states like California and Kentucky have much longer collection periods (20 years and unlimited, respectively). You need to check your specific state's rules.

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Ruby Knight

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One thing nobody's mentioned yet - make sure you file ALL missing returns at once. Don't file just the most recent year thinking you'll do the rest later. The IRS wants to see you completely back in compliance. Also, if you can pay even part of what you owe when you file, it shows good faith and can sometimes result in reduced penalties. I was in a similar situation (3 years unfiled) and managed to pay about 30% upfront, which helped tremendously with negotiating the rest.

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Is there a statute of limitations on how far back they can come after you for unfiled taxes? I'm worried they'll want returns from like 10 years ago even though I wasn't making much money back then.

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Ruby Knight

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The statute of limitations for the IRS to assess taxes is generally 3 years from the date you file your return. However - and this is important - there is NO statute of limitations on unfiled returns. The clock doesn't start until you actually file. For your situation, they typically focus on the last 6 years for unfiled returns, but technically they could go back further. That said, if you weren't making much money in those earlier years, it might not be worth their effort. My tax preparer advised me to focus on the last 6 years, but your situation might be different.

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Don't forget about state taxes too! Everyone's talking about the IRS, but your state tax authority might be even more aggressive about collection. Make sure you're addressing both federal AND state unfiled returns.

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This is so important. My brother dealt with the IRS fine on his back taxes but completely forgot about state taxes. California actually put a lien on his property before he even knew what was happening.

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NightOwl42

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Something similar happened at my workplace. For clarification - did your job duties change at all when they made this switch? Or did everything stay the same except how they paid you? Because that's a huge red flag. Also, do you receive directions from your boss, use their equipment, work set schedules, etc? Those are all signs you're an employee not a contractor. Your employer can't just decide to stop withholding taxes because they don't want to deal with the paperwork for part-timers.

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Nothing about my job changed at all - same duties, same desk, same boss giving me the same tasks and schedule. The only difference is they stopped withholding taxes and then sent me this 1099 instead of a W-2. I use all their equipment, work entirely on-site, and have zero control over my hours or how I complete my work.

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NightOwl42

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Yeah, that's textbook misclassification then. They can't just arbitrarily decide to treat you as a contractor while maintaining all the control of an employer relationship. They're doing this to save money on their end (employer-side taxes, benefits, etc.) while shifting the tax burden to you. I'd recommend documenting everything about your work arrangement - hours, supervision, equipment, etc. Then either talk to your employer about correcting this (if you think they'd be receptive) or follow the advice others have given about filing SS-8 and 8919 forms with the IRS.

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Quick question - did your pay rate increase when they switched you to 1099? Because if not, you're effectively taking a 7.65% pay cut since you're now responsible for the employer portion of FICA taxes. Many employers who do this "conversion" properly will increase the hourly rate to offset the tax difference.

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Not just 7.65% - it's more like 15.3% total for self-employment tax! Half would normally be paid by the employer, and half would be withheld from your paycheck. So if your pay didn't increase AT ALL, you're taking a massive hit.

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Nope, my pay stayed exactly the same. I had no idea about this tax difference until now. So I'm making the same hourly rate but will end up paying way more in taxes? That doesn't seem right at all...

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One thing nobody's mentioned - you should double check that this client is actually going to issue you a 1099-NEC. Some companies mistakenly think that categorizing someone as a "vendor" means they don't need to issue a 1099. If they paid you $600+ they're required to, but sometimes companies mess this up. If they don't send one, you still need to report all the income anyway. Just keep good records of all payments they made to you. And you might want to politely remind them now that they need to issue you a 1099-NEC by January 31st.

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AstroAce

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Thanks for bringing this up! I'm definitely worried they won't send the 1099 now. Should I just email them and explicitly ask if they'll be sending a 1099-NEC since I'm classified as a vendor in their system? I have all my payment records but would obviously prefer to have the official form.

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Yes, I'd recommend sending them a polite email asking for confirmation that they'll be issuing you a 1099-NEC for the 2024 tax year. Something like: "I understand I'm classified as a vendor in your system, and I just wanted to confirm you'll be issuing a 1099-NEC for tax purposes since the payments exceeded $600 this year." If they come back and say they don't issue 1099s to vendors, you can politely inform them that IRS rules require a 1099-NEC for independent contractors/vendors who were paid $600 or more for services. Sometimes the accounting department just needs a friendly reminder about the requirements.

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Just a quick tip: Some companies incorrectly use the term "vendor" for any external service provider in their accounting system, when they actually mean independent contractor. Their terminology doesn't change your tax status. However, definitely check with the other two clients as well. And start keeping track of your business expenses carefully - office supplies, software subscriptions, home office expenses if you qualify, etc. Those can really add up and reduce your taxable self-employment income.

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Do you need a different form to track expenses for a vendor vs a contractor? I always get confused about this stuff.

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Alicia Stern

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An important thing nobody has mentioned yet - look into whether you need to file state taxes as well as federal. Some states consider you a resident even after you move abroad if you haven't established residency elsewhere. What was your last state before moving to the UK? Some states like California and Virginia are notorious for trying to claim expats as tax residents. Also, be aware of FATCA (Foreign Account Tax Compliance Act) requirements. Your UK bank may have already reported your accounts to the IRS, which is why it's important to get compliant with your filings.

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This is a really good point about state taxes. I'm originally from California and they kept trying to claim me as a resident for tax purposes for years after I moved to France. I had to provide extensive documentation proving I had no intention of returning to California. Also, the FATCA thing is real - my French bank made me fill out a W-9 form once they realized I was a US citizen, and they definitely report my account information to the US authorities.

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Alicia Stern

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California is particularly aggressive about maintaining tax residency. They look for any connection (driver's license, voter registration, family ties, etc.) to claim you're still a resident. Other problematic states include New York, Virginia, and New Mexico. The FATCA reporting is a double-edged sword for expats. On one hand, it means the IRS likely already knows about your foreign accounts, which increases the importance of proper filing. On the other hand, it's caused some foreign banks to refuse US clients altogether due to the reporting burden. It's unfortunately part of the reality of being a US citizen abroad.

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Drake

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Does anyone know if the UK-US tax treaty helps with avoiding double taxation on investment income specifically? I'm also a US citizen in the UK, and while my UK employment income seems covered, I'm confused about how my US-based investments are treated.

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Sarah Jones

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The UK-US tax treaty does help with investment income but it's complicated. Generally, you can claim foreign tax credits in the US for taxes paid to the UK on the same income. For US-source investment income like your US investments, you'll typically pay US tax on those first, then declare them on your UK return and get credit for the US tax paid. For dividends specifically, the treaty usually reduces withholding rates. Interest and capital gains have their own rules too. I recommend keeping very clear records of all taxes paid in both countries so you can properly claim credits.

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