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Miguel Alvarez

Haven't filed taxes in over 10 years - what steps should I take to fix this now?

So I haven't filed or paid my taxes in over a decade (possibly closer to 15 years honestly). I know, I really messed up. The IRS and state tax authorities did levy my bank accounts several times years back when I was earning more. During the first 3-4 years of this period, my income was fairly good. After that, it dropped to under $26k annually. I was working as an independent contractor for a tech company but didn't get much out of it financially and left a few months ago with basically nothing. For most of this time, I didn't even have a properly registered business. I realize I've made some serious mistakes. Because I was worried about my tax situation, I never applied for any COVID relief programs (federal or state). I'm sure that opportunity is gone now. If I ever received any tax documents over these years, they're long gone. I don't have anything. I'm older now and trying to restart my life. I struggle with anxiety and depression, which hasn't helped this situation. Currently job hunting and really want to fix this tax mess. I'm hoping someone can give me advice that will both help ease my anxiety about this whole thing and guide me on practical next steps. What should I do to address this situation? Any advice would be deeply appreciated.

First, take a deep breath. You're not alone in this situation, and it's actually pretty common for people to go years without filing. The good news is that you're taking steps to fix it now, which is what matters. Start by requesting your wage and income transcripts from the IRS. You can do this online through the IRS website by creating an account, or by filling out Form 4506-T. These transcripts will show income reported to the IRS from employers, banks, etc. for the past 10 years. This gives you a starting point for what the IRS already knows about your income. For most individuals, the IRS generally only goes back 6 years for non-filed returns (unless they suspect fraud). So you might not need to file all 15 years. Focus on the most recent 6 years first. Since your income was under $26k for much of this time, you might actually be due refunds for some years rather than owing money. There's a 3-year limit on claiming refunds, but it's still worth filing to get into compliance. Consider getting help from a tax professional who specializes in back taxes and non-filer situations - specifically an Enrolled Agent or CPA with experience in this area. Many offer free initial consultations.

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Do you think it's better to use a tax pro for this or could someone reasonably figure this out on their own? Like if I use tax software and have those transcripts, would that work? I'm in a somewhat similar situation (about 7 years unfiled) and money is really tight.

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For someone with 7 unfiled years, it really depends on your comfort level with tax matters and how complicated your situation is. If you've only had W-2 income and standard deductions, tax software combined with your transcripts might be sufficient. If you had self-employment income, multiple income sources, or complex deductions, a professional would be worth the investment. Many tax pros who specialize in back taxes offer payment plans, and the peace of mind/protection from mistakes can be worth it. At minimum, consider getting a consultation to understand what you're facing before deciding to DIY.

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After dealing with a similar nightmare (8 years unfiled), I finally found help through https://taxr.ai - it seriously saved me so much stress. They specialize in helping people who haven't filed in years and need to get caught up. I uploaded what few documents I had, and they were able to help me figure out what I needed to file, what years were most important to focus on, and gave me a clear action plan. Their system can analyze your tax situation, determine which years you actually need to file for (sometimes you don't need to file all past years), and help you understand what you're actually dealing with. The whole process was much less scary than I expected. I was convinced I'd owe tens of thousands, but after getting everything sorted out, it was much more manageable than I feared.

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How exactly does it work? Do they file the returns for you or just tell you what to do? I've got about 5 years unfiled and honestly I'm terrified to even look at my situation.

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I'm skeptical about online services for something this serious. Did you end up having to talk to the IRS directly or did they handle everything? My situation is pretty messy with some 1099 work and some W2 jobs I only worked briefly.

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They don't file the returns for you, but they analyze your situation and give you a complete plan of action. They help you understand which years you actually need to file, what documents to gather, and estimate what you might owe. It takes the guesswork out of the process. I did end up talking to the IRS myself for a couple of things, but I felt prepared because I knew exactly what I was dealing with. For your situation with mixed 1099 and W2 income, that's actually perfect for their system since it can help sort through complicated income situations and make sure you're claiming all possible deductions for your 1099 work.

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Just wanted to update after trying taxr.ai that the previous commenter recommended. It was actually really helpful for my situation. I was absolutely dreading dealing with my unfiled taxes, but their system made it much clearer what I needed to do. The transcript analysis feature was especially useful - showed me exactly what income the IRS already knew about for each year. Turns out for 2 of my unfiled years, I was actually due refunds! The other 3 years I owe, but the amounts were way less than the nightmare scenarios I had built up in my head. The step-by-step plan they created made the whole process feel manageable. Just filed my first two years last week, and working on the rest now. Wish I hadn't waited so long to address this!

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Another thing that really helped me when I was in a similar situation was using Claimyr (https://claimyr.com) to actually get through to the IRS. I spent WEEKS trying to call them directly and would either get disconnected or be on hold for hours. Claimyr got me connected to an actual IRS agent in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I was skeptical at first, but when I finally got to speak to someone at the IRS, they were actually quite helpful about my unfiled returns. The agent walked me through exactly what I needed to do and even put some notes on my account about my case. Having that direct conversation with the IRS gave me peace of mind that I was on the right track instead of just guessing what I needed to do. They confirmed which years I needed to focus on and explained the process clearly.

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How does this even work? The IRS phone system is notoriously impossible to get through. What's the catch? I've been trying to reach them for months about my own situation.

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Sounds like a scam to me. I don't believe anyone can magically get through the IRS phone queue when millions of people are trying. And even if you do get through, why would the agents be helpful rather than just trying to collect?

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It uses a legitimate system that businesses use to navigate phone trees and stay on hold, so there's no "magic" to it. They basically wait on hold for you and call you when an agent picks up. The reason IRS agents were helpful rather than just trying to collect is because contrary to popular belief, many IRS employees genuinely want to help taxpayers get into compliance. When you're proactively trying to fix your situation, they often work with you. They explained my options, including payment plans and in some cases, the Fresh Start program for those who qualify. It's in their interest to help people file properly rather than stay in the shadows.

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I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I was desperate enough to try it because I needed answers about my unfiled returns. It actually worked exactly as described - got a call back in about 45 minutes and was connected to an IRS representative who was surprisingly patient with my situation. The agent explained that for my case, I only needed to file the last 6 years to get back into compliance, not all 10 years I was worried about. They also outlined the penalty abatement options I might qualify for once I file. It was such a relief to have real information instead of just anxiety-inducing guesswork. If you're in a similar situation, having an actual conversation with the IRS is incredibly clarifying.

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One important thing to consider - if you had very low income during some of those years, you might not have been required to file at all. For 2023, for example, if you're single and under 65, you don't need to file if your income was less than $13,850. But even if you weren't required to file, it might be beneficial to do so if you had any federal tax withheld from paychecks or are eligible for refundable credits like the Earned Income Credit. Also, don't forget to check your state's filing requirements which are often different from federal requirements. Some states have much lower thresholds for mandatory filing.

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If someone was 1099 though, wouldn't they have to file regardless of income level? I thought there was like a $400 self-employment threshold where you have to file even if your income is super low?

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You're absolutely right about self-employment income. If you had net self-employment income of $400 or more, you must file a return regardless of your total income level. This is because you'd need to pay self-employment tax (Social Security and Medicare). This is a common misunderstanding that gets people in trouble - many think the standard filing thresholds apply to all income types, but self-employment has that much lower $400 threshold. Since the original poster mentioned working as an independent consultant, they likely needed to file even during their lower income years.

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I went through this last year. Let me tell you what worked for me: Get on a payment plan as soon as possible after filing. IRS Fresh Start program was a lifesaver. They let me pay a small amount monthly based on my actual ability to pay. Also, after you file all required returns, you can request penalty abatement through Form 843. I was able to get first-time penalty abatement which eliminated a ton of the failure-to-file penalties for my earliest unfiled year. Didn't help with interest, but still saved thousands. Don't forget about state taxes! Each state has different requirements and lookback periods. Some states (like CA where I am) can be even more aggressive than the IRS about collection.

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Thx for the penalty abatement tip! Did they give you any trouble about approving it? How long did the whole process take from when you first filed your back taxes to getting the payment plan and abatement?

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I really appreciate everyone sharing their experiences here. As someone dealing with anxiety and depression like you mentioned, I want to emphasize that taking action - even small steps - really does help reduce the overwhelming feeling about this situation. One thing that helped me personally was breaking it down into very manageable chunks. Week 1: just request transcripts. Week 2: organize what I found. Week 3: tackle one year at a time. The mountain becomes much more climbable when you're not trying to solve everything at once. Also, don't beat yourself up about the COVID relief programs you missed. Focus on what you can control moving forward. The IRS genuinely wants people to get back into compliance, and there are more options available than most people realize. Consider reaching out to a Low Income Taxpayer Clinic (LITC) in your area if money is tight. They provide free or low-cost representation and can help navigate the process. You can find one through the IRS website or by calling the Taxpayer Advocate Service at 1-877-777-4778. You're taking the right steps by addressing this now. It's never too late to get back on track.

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