Need urgent help - haven't filed my taxes since 2018! SOS!

I'm in a bit of a panic right now. Just found out that the person who was supposed to be handling my taxes hasn't filed ANYTHING since 2018! 😳 I know this is totally on me for not checking and I take full responsibility for being negligent. I've decided it's time to stop relying on others and take control of this mess myself. Already requested and received my tax transcripts from the IRS, but now I'm completely lost about what to do next. Should I tackle each unfiled year separately, or is there some more efficient approach? Is there specific software that works best for filing multiple back years? I'm really overwhelmed but determined to fix this. I've thought about hiring a professional, but I actually want to learn how to do this myself so I can handle my taxes properly going forward and maybe even help friends and family who might be in similar situations. This whole disaster has actually sparked an interest in tax preparation for me - I'm even considering pursuing certification as an Enrolled Agent or maybe studying accounting. I figure turning this negative into something positive would be worthwhile. Any guidance, resources, or advice would be SO appreciated. I'm ready to dig in and fix this!

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18 comments

Emma Johnson

•8M

So you're in what's called a "back filing" situation. Don't panic! This is more common than you think, and the IRS actually appreciates when people come forward voluntarily to file past returns. Start by organizing your tax documents by year - W-2s, 1099s, etc. If you're missing anything, your tax transcripts will help, but you might need to contact previous employers for copies of W-2s. I recommend filing chronologically, starting with 2018 and working forward. For back taxes, you'll need to use the tax forms specific to each year - the tax laws change annually, so you can't use current year forms for past years. For software, many major tax programs like FreeTaxUSA offer prior year returns at reasonable prices. You'll need to mail in physical copies of these returns since e-filing typically closes after about 3 years. Be prepared for potential penalties and interest, but filing voluntarily is WAY better than waiting for the IRS to find you. If you owe a significant amount, you can look into payment plans once everything is filed.

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Emma Johnson

•8M

You might qualify for penalty abatement, especially if this is your first time having compliance issues. Look into the IRS First-Time Penalty Abatement policy - it's worth requesting once you've filed everything. The IRS can be surprisingly reasonable when you're proactively fixing the situation. Yes, you absolutely need to file state taxes for all those years too. Each state has its own procedures for back filing, so you'll need to check with your specific state's tax authority. Some states have more favorable penalty structures than the federal government.

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Astrid Bergström

•8M

I was in a similar situation last year with 4 unfiled years. What really helped me was using taxr.ai (https://taxr.ai) to analyze all my tax documents. I was completely overwhelmed with all the W-2s, 1099s, and old investment statements I had collected. The tool basically scanned everything, organized it by year, and helped me understand what I was missing. It even found some deductions I would have completely missed on my own! Felt like having a virtual tax assistant helping me sort through the chaos. After getting everything organized, filing the back years was actually not as horrible as I expected. Still took time, but at least I knew I wasn't missing anything important.

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Astrid Bergström

•8M

Yes, it definitely handles self-employment tax situations. It helps organize your 1099 income and categorizes business expenses properly for Schedule C. It was actually really good at identifying which expenses were deductible and which weren't based on IRS guidelines. It saved me from making some questionable deductions that might have triggered an audit. I understand the concern about pricing transparency. They actually offer different tiers based on how many documents you need analyzed and how many tax years you're dealing with. I don't remember the exact pricing, but I found it reasonable considering the alternative of paying a CPA hundreds per return for multiple years. You can start with a basic analysis and upgrade if needed.

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Omar Farouk

•8M

So I took the plunge and tried taxr.ai after seeing the recommendation here. It was seriously a game-changer for my back tax situation! I had tax documents scattered across email accounts, old laptops, and paper files. The system analyzed everything and organized it by tax year which saved me hours of sorting. What impressed me most was how it flagged potential deductions I would have completely missed - like some charitable donations I had forgotten about and some education expenses that were deductible. This actually reduced what I owed for a couple of years. I still had to file each return separately, but having all my information properly organized made it so much more manageable. Now I'm just waiting for my payment plan to be approved. Huge relief to have this weight off my shoulders!

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Chloe Martin

•8M

If you end up owing back taxes (which is likely with multiple unfiled years), prepare for the nightmare of trying to reach the IRS to set up a payment plan. I spent literally WEEKS trying to get through to a human being. Would call, wait on hold for 2+ hours, then get disconnected. I finally found this service called Claimyr (https://claimyr.com) that 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 After spending so much time dealing with automated systems and hold music, it was such a relief to finally talk to someone who could actually help set up my payment plan. Saved me countless hours of frustration.

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Chloe Martin

•8M

It's not about "skipping the line" - they use a technology that navigates the IRS phone tree and waits on hold for you. When they finally get through to a human agent, they call you and connect you directly. So instead of you personally waiting on hold for hours, their system does it. They don't have any special access to the IRS - they're just automating the painful hold process that most people don't have the patience for. I was skeptical too, but when you've been trying to reach the IRS for weeks with no success, it's worth considering alternatives.

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Anastasia Kuznetsov

•8M

Ok I need to apologize to whoever recommended Claimyr above. I thought it sounded like a total scam but I was desperate after trying to call the IRS for 3 days straight and never getting through. It actually worked exactly as described. Their system waited on hold (for over 2 hours!) and then called me when they got a human on the line. I was connected to an IRS agent who helped me set up a payment plan for my back taxes. Saved me from taking another day off work just to sit on hold. Sometimes I hate being wrong but in this case I'm glad I was! Now I have an installment agreement for the $7,800 I owed and can finally sleep at night.

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Sean Fitzgerald

•8M

One thing nobody's mentioned yet - you might actually be owed refunds for some of those years! The IRS only has 3 years to issue refunds, so anything before 2022 would be forfeit now, but still worth checking. I'd also recommend preparing for a potential CP2000 notice if you had income reported to the IRS that you haven't accounted for. Once you start filing, they'll match your reported income against what they have on file. Keep good records of EVERYTHING during this process. Every letter, every payment, every confirmation number. The IRS systems don't always talk to each other efficiently.

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Sean Fitzgerald

•8M

The IRS will generally apply any refunds to outstanding tax debts automatically. So yes, if you're due a refund for 2022 but owe for 2018, they'll typically apply that refund to reduce your 2018 balance. This happens automatically in most cases. A CP2000 is a notice of proposed adjustment to your tax return. It basically means "we think you didn't report all your income." It's not an audit, but it means the IRS identified a discrepancy between what you reported and what they have on record from W-2s, 1099s, etc. Not something to panic about, but you'll need to either agree with their assessment or provide documentation showing why they're incorrect.

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