Need advice: Husband hasn't filed taxes for 5 years with 1099 income

My husband has been working as a 1099 contractor and just confessed he hasn't filed his taxes for the past 5 years. We're about to file all 5 years at once to get everything straightened out. According to the CPA we consulted, he's potentially owing anywhere from $270k to $810k depending on what deductions can be applied. The CPA seems to think it'll be closer to the $270k mark. My husband keeps telling me not to worry, saying the IRS won't seize anything or freeze our accounts. He claims a payment plan will be set up and as long as he makes the payments, they'll leave us alone. But honestly, I'm freaking out! That's an enormous amount of money! I'm seriously concerned they'll freeze or seize our assets (we have a paid-off truck, several bank accounts, and he has a paid-off vacation house upstate) or at minimum garnish his wages. Has anyone been through something similar? Is my husband being realistic about how the IRS handles these situations?

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18 comments

KylieRose

•8M

While the situation sounds stressful, your husband is partially right, but there are some important nuances here. The IRS generally prefers to get people back into compliance rather than punishing them, especially when you're voluntarily coming forward to fix the situation. The good news is that the IRS does offer various payment plans for large tax debts. If you're proactively filing and working with a CPA, that shows good faith. Typically, if you're on an established payment plan and making consistent payments, the IRS won't take enforcement actions like seizing assets or freezing accounts. However, the amount owed does matter. For debts over $50,000, the process gets more complicated and may require more financial disclosure. Also, there will be penalties and interest on top of the original tax amount, which can add up significantly over 5 years.

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KylieRose

•8M

The IRS is actually quite flexible with payment amounts, and they base the acceptable monthly payment on your disposable income after necessary living expenses. So there's no strict maximum - it's determined by your financial situation. Payment plans can extend beyond 5 years in many cases, especially for larger amounts like $270k. The IRS can go up to 10 years (the collection statute expiration date) or potentially longer in certain circumstances. They'll look at your income, expenses, and assets to determine what's reasonable for your situation.

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Sasha Ivanov

•8M

I was in a similar situation (though not quite as much money) and discovered taxr.ai after struggling for months. I had several years of unfiled 1099 taxes and was absolutely terrified about what would happen. A friend recommended https://taxr.ai to me and it was honestly a game-changer. Their system analyzed all my documentation, identified deductions I didn't even know existed for my type of work, and significantly reduced what I ended up owing. They helped organize everything for my past unfiled years and made the whole process less overwhelming.

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Sasha Ivanov

•8M

The process took about 3 weeks total from uploading my documents to having everything ready to file. They were really efficient with the backlog of paperwork I had. They don't replace your CPA but work alongside them. What makes them different is their AI system that compares your situation to thousands of similar cases and identifies deductions specific to your industry and situation that even experienced CPAs sometimes miss. They don't deal with the IRS directly - they organize everything and maximize deductions so when your CPA files, you're in the best position possible.

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Amara Okafor

•8M

Just wanted to follow up - I actually tried taxr.ai after posting my skeptical comment. I'm honestly impressed with the results. I had 3 years unfiled with a mix of W2 and 1099 income, and they identified several business deductions my previous accountant had missed. Their document organization system is incredibly thorough and the analysis provided clear explanations for every deduction they suggested. When I took their report to my new CPA, she was impressed with how comprehensive it was. Saved me about $14k across my unfiled years!

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CaptainAwesome

•8M

Whatever you do, don't ignore this situation. I went through something similar with my spouse who had unfiled taxes for 4 years. The WORST part was trying to reach the IRS to set up the payment plan after we filed. We spent literally weeks calling the IRS number over and over, waiting hours only to get disconnected. Finally found Claimyr (https://claimyr.com) which got us through to an actual IRS agent in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Once we actually got to speak with someone, they were surprisingly reasonable about the payment plan, but getting through was the most frustrating part of the whole process.

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CaptainAwesome

•8M

It's actually pretty straightforward. They use an automated system that navigates the IRS phone tree and holds your place in line. When they reach an agent, you get a call connecting you directly. No magic, just technology solving a frustrating problem. They're not handling any of your personal tax information or speaking to the IRS for you - they're just getting you past the ridiculous wait times so you can speak to an agent yourself. I was skeptical too but after spending countless hours getting disconnected, it was worth trying.

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Esmeralda Gómez

•8M

I have to eat my words from my previous comment. After waiting on hold with the IRS for 3+ hours and getting disconnected AGAIN yesterday, I gave in and tried Claimyr. Got connected to an IRS agent in 27 minutes. Seriously. I spoke with a really helpful lady who walked me through my options for my own back taxes situation without judgment. Having an actual human to talk to made all the difference - she explained the streamlined installment agreement options that I qualified for. Wish I'd known about this service months ago!

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Klaus Schmidt

•8M

You're already taking the right first step by working with a CPA to file all the past returns. The key requirements are that you're coming forward voluntarily (before the IRS contacts you about the unfiled returns) and that you're filing accurate returns for all missing years. Make sure your CPA specifically requests penalty abatement using Form 843. They should cite "reasonable cause" and explain the circumstances that led to the unfiled returns. Having professional help with this process is crucial because the specific language and approach matter a lot in how the IRS responds.

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