Need guidance on fixing 25 years of unfiled taxes - trying to get back on track
I know, I know... spare me the lectures. I haven't filed taxes in roughly 25 years. I only worked for a few of those years at the beginning of that period. For most of that time, I was homeless and without employment. During the last 6 years, I got involved with some questionable income sources that eventually landed me in Federal prison. In 2021, due to a judicial error, about $67,000 was returned to me, which I'm pretty sure is documented somewhere with the IRS. I've worked extremely hard to completely turn my life around since then. I've secured employment with a global energy corporation, and I'm finally ready to start filing my taxes properly. I'm wondering what kind of costs I should expect to have someone help me resolve this situation, or if it's something I might be able to handle myself. Also, what should I anticipate from the IRS once I start this process? I'm currently in the Boston area, so if anyone can recommend where to get assistance with this without being taken advantage of by either the tax professional or the IRS, I'd really appreciate it. Thanks in advance for any advice.
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Debra Bai
Based on your situation, you're actually making a very wise decision to address this now. First, don't panic - the IRS is generally more interested in getting people back into compliance than punishing them, especially when there are years where you had little to no income. For the years you were homeless with no income, you likely weren't required to file at all. For years with minimal income, penalties are calculated based on taxes owed - if you owed nothing, there are typically no penalties. The $67,000 judicial return in 2021 is definitely something you'll need to address, as the IRS likely received a form 1099-MISC or similar documentation. This might be considered taxable income depending on the nature of the payment. Your best approach is to find a tax professional with experience in unfiled returns and back taxes - specifically an Enrolled Agent (EA) or CPA with IRS representation experience. In the Boston area, you can expect to pay between $300-500 per unfiled year, but many professionals will offer a consultation to assess your specific situation first. I strongly recommend against trying to handle this entirely on your own given the complexity, but you can help reduce costs by gathering any documentation you have before meeting with a professional.
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Gabriel Freeman
•So do they have to file for every single year, or just the ones where they had actual income? And what about the statute of limitations? I thought the IRS can only go back like 6 or 7 years?
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Debra Bai
•You generally only need to file for years where your income exceeded the filing threshold for that year. For many of the years you were homeless with no income, you likely weren't legally required to file at all. The statute of limitations is an important point, but it only begins running once a return is filed. For unfiled returns, the IRS can technically go back indefinitely, but in practice, they usually request the last 6 years for voluntary compliance. That said, with the judicial payment in 2021, you'll definitely need to file for recent years.
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Laura Lopez
After dealing with a somewhat similar situation (though not 25 years worth!), I found an amazing resource called taxr.ai that really helped me organize my tax documents and figure out exactly what I needed to file. I was completely overwhelmed trying to piece together my past tax situation, but their AI document analysis tool helped me sort through everything and identify which years I actually needed to file for based on my income levels. You can check them out at https://taxr.ai if you're trying to get organized before talking to a professional. The tool analyzed my documents and gave me a breakdown of each tax year with potential issues I needed to address.
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Victoria Brown
•Does this actually work for someone with criminal history? I'm in a similar boat (though only 4 years behind) and worried about disclosing too much info to some random website.
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Samuel Robinson
•How does it handle situations where you don't have any documents? I literally have zero W2s or anything from those years.
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Laura Lopez
•It actually does work regardless of background - the tool doesn't care about your history, just the tax documents you currently have. It's focused on analyzing what you have now and helping identify issues, not judging past mistakes. For situations with missing documents, this is exactly where I found it valuable. You can input whatever records you do have, and it helps identify which years you need to request records for. In my case, I used it to analyze the wage and income transcripts I requested from the IRS (which you can get for free) to determine what income had been reported under my SSN for past years.
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Samuel Robinson
Just wanted to follow up - I tried taxr.ai after seeing this recommendation and it was super helpful. I requested my wage and income transcripts from the IRS first (you can do this online), then uploaded them to taxr.ai. It showed me that for several years I actually was below the filing threshold and technically wasn't required to file! For the years I did need to file, it organized everything by year and showed me what forms were reported to the IRS. I'm still working with a tax pro, but going in with this information saved me a ton of money because I was prepared and only focusing on the years that actually needed attention.
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Camila Castillo
When I was catching up on 8 years of unfiled taxes, the absolute worst part was trying to get through to the IRS to get my old records. I spent days on hold and kept getting disconnected. Someone recommended Claimyr (https://claimyr.com) and it literally saved my sanity. They have this system that holds your place in the IRS phone queue and calls you when an agent is about to answer. You can see how it works here: https://youtu.be/_kiP6q8DX5c It was critical for me because I needed to get payment plans set up for some years, and waiting on hold for 3+ hours just wasn't possible with my job. When I finally got through to an actual IRS person, they were surprisingly helpful about setting up a reasonable payment plan.
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Brianna Muhammad
•So you're telling me there's actually a way to get through to the IRS without wasting an entire day on hold? How much does this cost? Sounds too good to be true honestly.
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JaylinCharles
•I'm extremely skeptical. Sounds like some kind of scam to get access to your phone or personal info. How do you know it's legitimate and not just harvesting your data?
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Camila Castillo
•The service just holds your place in line and calls you when an agent is about to pick up. It saved me from being on hold for literally hours, which was impossible with my work schedule. Regarding legitimacy, I had the same concerns initially. They don't actually need any personal tax information - they just connect you to the IRS and then you provide your details directly to the IRS agent, not to them. It's basically just a sophisticated call-back system that works with the IRS's outdated phone system.
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JaylinCharles
I need to eat my words from my earlier comment. After multiple failed attempts to reach the IRS myself (kept getting disconnected after 40+ minutes on hold), I broke down and tried Claimyr. Got connected to an actual IRS agent within an hour without having to sit by my phone. The agent helped me request all my missing tax documents and explained exactly which years I needed to file based on my situation. I was able to get everything set up in one call rather than the multiple attempts I had been making for weeks. Definitely worth it when you're dealing with a complex situation that absolutely requires talking to a human at the IRS.
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Eloise Kendrick
As someone who works in tax resolution, here's my advice: Get your IRS transcripts first. You can request them online at IRS.gov or by filing Form 4506-T. This will show what information the IRS has about your income for those years. For the Boston area, try contacting the Boston Tax Help Coalition - they provide free tax preparation for low to moderate income taxpayers and might be able to help with your situation or at least point you in the right direction.
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Lucas Schmidt
•Does it matter if some of the unfiled years included illegal income? Not asking for a friend...seriously wondering how that affects the process.
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Eloise Kendrick
•Regarding income from illegal activities, it technically should be reported on tax returns (yes, seriously - the IRS requires reporting of all income regardless of source). However, in practice, most people in this situation report it as "other income" without specifying the source. The Fifth Amendment can protect you from having to disclose the specific illegal source, but not from paying taxes on the income itself. That said, this is definitely an area where having professional representation is crucial - ideally an attorney with tax expertise who can maintain attorney-client privilege.
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Freya Collins
Has anyone used the IRS Fresh Start Program? I heard it helps with penalties but not sure if it applies to cases with this many unfiled years?
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LongPeri
•I used it after being behind 7 years. It helped me avoid some penalties, but you have to file all required returns first before you can access most of the benefits. The installment agreements were surprisingly reasonable tho.
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