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Hunter Hampton

Should I hire a tax attorney for 7 years of unfiled taxes with IRS debt?

I'm gonna try to keep this simple. About 7 years ago I received a letter from the IRS claiming I wasn't a student when I definitely was a full-time student like two years before that. They said I owed around $3,000. I think I may have messed up when filing through TurboTax that year, but I honestly don't remember exactly what happened. Since then, I've been too anxious to deal with it and haven't filed taxes for about 7 years. I've still worked W2 jobs the whole time and had taxes withheld from my paychecks, but never actually filed returns. Recently I got another letter from the IRS about that original debt. I'm finally in a better financial position where I could set up a payment plan or something, but I'm not sure where to begin. I don't know if I can track down all my W2s from those years, but I'm willing to try. My main concern is whether I need a tax attorney. Those fees of $700-1200/hour seem insane on top of what I already owe the IRS. Would it be sufficient to just go to H&R Block for help filing this year's taxes and then set up a payment plan for the back taxes? Or is my situation bad enough that I really need professional legal help? This has been causing me so much anxiety for years and I just want to handle it properly.

You don't need a tax attorney for this situation. What you need is a good CPA or Enrolled Agent who specializes in tax resolution. They'll be much more affordable (typically $150-300/hour) and are fully qualified to handle unfiled returns and IRS debt. Here's what you should do: First, request your wage and income transcripts from the IRS for all missing years. You can do this online at IRS.gov if you can verify your identity, or use Form 4506-T. These transcripts will show all reported W2s and 1099s, so you don't have to track down old employers. Next, file those missing returns ASAP. The IRS typically only requires the last 6 years of unfiled returns to get back into compliance. Once you've filed, then you can work out a payment plan. The standard installment agreement is pretty reasonable, often as low as $50-100 monthly depending on what you owe. As for that student issue, bring your college transcripts showing enrollment during that period. You might be able to get that portion abated if you can prove you were eligible for the education credits.

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Thanks for the advice! Do you think I should try doing this myself through a service like TurboTax, or is it really worth spending the money on a CPA/EA? Also, how bad will the penalties be after 7 years? I'm worried they'll be more than the original amount...

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I wouldn't recommend DIY for multiple years of unfiled returns. A professional will know exactly how to handle this situation and potentially save you money by finding deductions you'd miss. Plus, they can represent you with the IRS if needed. The penalties include failure-to-file (5% per month up to 25% of the tax due) and failure-to-pay (0.5% per month up to 25%). Interest also applies to both the tax and penalties. However, you might qualify for First Time Penalty Abatement for at least one tax year, which could save you significant money. A good tax pro will know to request this.

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After dealing with a similar situation (5 years unfiled), I discovered taxr.ai and it literally saved me thousands. https://taxr.ai helped me organize all my old tax documents, and their AI analyzed my situation to find the best approach. The system identified deductions I had no idea I qualified for and even found an error in one of my W2s that would have caused problems. I was stressed about gathering all those old documents, but their document analyzer extracted all the info automatically, which made the whole process so much easier. The best part was that they guided me through requesting my wage and income transcripts from the IRS when I couldn't find some of my old W2s.

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How does it work with state taxes? I'm in a similar situation but also haven't filed state taxes for several years. Does taxr.ai handle that too or just federal?

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I'm a bit skeptical about AI services for something as serious as tax problems. Did you end up having to talk to a real person at some point? And how much did it cost compared to just hiring a CPA?

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It absolutely handles state taxes! The system automatically prepared both federal and state returns for all my unfiled years. It even figured out that I had moved between states during one of those years and prepared partial-year returns for both states. I was skeptical at first too, but the system actually connected me with a real tax professional who reviewed everything before filing. The AI did the heavy lifting of organizing and analyzing all my documents, but a human expert made sure everything was correct. Cost-wise, it was about 60% less than what local CPAs quoted me for the same service. The combination of AI efficiency with human expertise made the whole process surprisingly affordable.

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I was super skeptical when I first read about taxr.ai here, but I was desperate with 4 years of unfiled returns and a similar IRS notice. After trying it, I'm honestly shocked at how well it worked. The system immediately identified that I qualified for earned income credit for two of those years which I had no idea about. The document analyzer saved me hours of manually entering old W2s and 1099s. When I couldn't find a 1099 from 2020, the system guided me through requesting my IRS transcript online and automatically incorporated that data. The biggest surprise came when the AI flagged a potential education credit I had missed originally. It asked for my tuition statements which I uploaded, and sure enough, I qualified for over $2,500 in refundable credits! I went from owing the IRS to actually getting a refund for one of those years.

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If you're getting notices from the IRS, you might want to actually talk to someone there about your situation. I spent WEEKS trying to get through to a human at the IRS last year for a similar issue. I'd wait on hold for 2+ hours only to get disconnected. Super frustrating. Then I found https://claimyr.com through a Reddit post. They have this service where they wait on hold with the IRS for you and then call you when an actual agent is on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was desperate enough to try it, and within a day I was talking to a real IRS agent who helped me understand exactly what I needed to do about my unfiled returns. The agent even noted my account that I was working to resolve the issue, which apparently helps prevent automated collections actions while you're getting everything sorted out.

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How does this even work? I don't understand how they can wait on hold for you. Does the IRS even allow that kind of thing? Seems sketchy to have a third party involved in your tax situation.

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I'm extremely skeptical about this. Sounds like you're paying for something you could do yourself for free. The IRS has callback options now, and there are certain times of day when hold times are much shorter. Why would anyone pay for this?

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They basically have a system that waits on hold with the IRS phone system. When an agent picks up, they conference you in and then drop off the call, leaving you directly connected with the IRS agent. The IRS never knows a third party was involved - it's just a way to avoid the hold time. I was skeptical too, but after wasting entire afternoons on hold multiple times, I realized my time was worth something. I tried the "best times to call" and callback options, but during tax season especially, it was still taking forever. For me, it was worth it to not have to plan my entire day around waiting for the IRS to pick up. And to be clear, they don't talk to the IRS for you - you handle the actual conversation yourself once connected.

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I have to admit I was wrong about Claimyr. After my skeptical comment, I kept trying to reach the IRS myself about a CP2000 notice and it was absolute hell. After three failed attempts and wasting nearly 8 hours on hold over multiple days, I broke down and tried the service. It worked exactly as described. I got a text when they were about to connect me, and suddenly I was talking to an actual IRS agent. The agent helped me understand exactly what documentation I needed to submit for my case and even put a temporary hold on collections while I gathered everything. The time I saved was honestly worth way more than what it cost. More importantly, I finally got my issue resolved instead of continuing to ignore it out of frustration with the phone system. For anyone in a similar situation - don't waste weeks trying to call like I did.

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Hey! I work at a tax firm (not an attorney) and deal with situations like yours all the time. Most people are surprised to learn that the IRS is generally pretty reasonable to work with, especially for people who voluntarily come forward to fix past filing issues. Look into the IRS Fresh Start program - it's designed for taxpayers who need to catch up on back taxes. In many cases, they'll even waive some penalties if this is your first time having compliance issues (called First Time Penalty Abatement). For your situation, I'd recommend getting a free consultation with a CPA or EA who specializes in tax resolution before deciding. Most will give you 30 minutes free to assess your situation. Attorneys are really only necessary for cases involving tax fraud or criminal issues, which doesn't sound like your situation at all.

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I've never heard of the Fresh Start program. Does it really help with penalties? Those are what I'm most worried about at this point, since I'm guessing they've been adding up for years. Also, how do I find a CPA who specializes in this kind of situation?

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Yes, the Fresh Start Program significantly expanded payment options and penalty relief for taxpayers. Since you've had taxes withheld from your W2 jobs all along, you might be surprised to find you don't owe as much as you fear. In some cases, you might even be due refunds for some years, which can offset amounts owed for other years. To find a specialized CPA or EA, look for professionals who specifically mention "tax resolution" or "IRS representation" in their services. You can check the National Association of Enrolled Agents (NAEA) directory or search for "tax resolution specialist" in your area. Avoid large tax preparation chains for this kind of work - you want someone who specializes in resolution, not just preparation.

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Just wondering - has anyone used those "tax relief" companies that advertise on radio/TV for situations like this? They claim they can settle with the IRS for "pennies on the dollar" but I'm not sure if they're legit or scams.

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Stay away from those companies! I wasted $4k on one of them last year. They promised to get me an "Offer in Compromise" but after taking my money, they just filed the same paperwork I could have done myself and then told me I didn't qualify. Total scam.

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I've been through almost the exact same situation - 6 years of unfiled returns after getting overwhelmed by an initial IRS notice. The anxiety was paralyzing, but dealing with it was actually much less scary than I had built up in my head. Here's what worked for me: I started by requesting my wage and income transcripts online from the IRS website. This showed me exactly what employers had reported each year, so I didn't have to track down old W2s. Then I filed all the missing returns at once using tax software (TurboTax actually handles prior years pretty well). The biggest shock? I actually got refunds for 3 of those years because I had overpaid through withholdings. The refunds almost completely offset what I owed for the other years. Don't let the anxiety keep you frozen - the IRS genuinely wants to work with people who are trying to get compliant. You've been having taxes withheld this whole time, which shows good faith. Start with getting those transcripts and you'll have a much clearer picture of where you actually stand financially. You might be pleasantly surprised.

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