I haven't filed taxes in over a decade and want to catch up - what steps should I take?

Hey everyone, I'm in a bit of a tax mess and could use some guidance. I haven't filed federal or state taxes in probably 12-13 years and I'm trying to finally get this sorted out. In the past, both the IRS and my state tax agency have levied my bank accounts a few times (this was years ago when I was making better money). For context, during the first 3-4 years of this gap, I was earning a decent income - maybe $65-70k. But for the last 8-9 years, I've been making under $25k annually. I was working as an independent contractor for a tech company but didn't have anything formally registered as a business. I finally ended that relationship about 6 months ago and walked away with basically nothing. I've made some poor decisions along the way. Because I was worried about my tax situation, I never applied for any pandemic assistance programs that I probably qualified for. That opportunity is gone now. At this point, I should assume I don't have access to ANY tax documents from previous years. I'm in my late 40s and trying to rebuild my life. I struggle with anxiety and depression, which hasn't helped this situation. I'm currently job hunting and want to clean up this tax mess before starting fresh. What should my first steps be to address this? How bad is my situation likely to be? Any advice would be so appreciated - both to ease my mind and help me move forward with a plan.

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18 comments

Isabella Santos

•8M

First, take a deep breath. You're not alone in this situation, and the fact that you're taking steps to fix it is actually a big positive that the IRS will appreciate. Here's what I suggest as your next steps: Get your wage and income transcripts from the IRS. You can request these online through the IRS website by creating an account at IRS.gov. These will show what income was reported to the IRS under your SSN for each year. This gives you a starting point for what you earned. For the years where your income was under $25k, you may actually be below the filing threshold for some of those years, especially if you were single with no dependents. This could reduce how many returns you actually need to file. Focus on the last 6 years first. While technically all unfiled years should be addressed, the IRS generally focuses on the last 6 years for bringing non-filers into compliance. Get those years filed, and then you can work on older years if needed. Look into the IRS Fresh Start program. Given your financial situation and the length of time, you might qualify for an Offer in Compromise or a payment plan with reasonable terms. Don't try to tackle this alone - consider hiring a tax professional who specializes in back taxes and non-filer situations. Many offer free consultations where they can assess your specific situation.

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Isabella Santos

•8M

Yes, your wage and income transcripts will show any 1099 income that was reported to the IRS for your independent contractor work, along with any other income that was reported under your SSN. This gives you a good starting point, though it won't show income that wasn't properly reported. For the Offer in Compromise, that's exactly right - it's a program where the IRS agrees to settle your tax debt for less than the full amount you owe. They look at your ability to pay, income, expenses, and asset equity. Given your income history and current situation, you might be a good candidate, but they do require you to be current with all filings before applying.

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StarStrider

•8M

I was in a similar situation a few years back (not quite as many years but still pretty bad) and I discovered taxr.ai (https://taxr.ai) which was a lifesaver. I was missing a ton of documents and they helped me locate my past income records and create a reasonable estimate for years where I had gaps. It was WAY less stressful than trying to piece everything together myself or paying a tax pro thousands of dollars upfront. They basically analyze your available records and help reconstruct your tax situation for years where you're missing information. In my case, they found income sources I'd completely forgotten about and helped me understand which years I might actually be below filing thresholds.

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StarStrider

•8M

They don't have special access to IRS records, but they use a combination of document analysis and AI to help reconstruct your tax history. You'd need to request your transcripts from the IRS first (which is free), and then they analyze those along with any other documents you might have. For years with gaps, they help create reasonable estimates based on your work history and industry standards. They don't file the returns for you - they provide the reconstructed information and guidance that you can use to file yourself or give to a tax preparer. What I found helpful was that they provided a detailed explanation of each year's situation so I could understand exactly what I was dealing with, including potential penalties and whether I might qualify for relief programs.

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Freya Pedersen

•8M

Just wanted to give an update - I ended up trying taxr.ai after my skeptical comment above. I was impressed with how thorough they were. They analyzed my transcripts and found several years where I was actually under the filing threshold, which saved me from having to file for those years. For the years I did need to file, they helped me identify deductions I would have missed on my own. Still owe some money, but WAY less than I feared. The peace of mind alone was worth it after years of tax anxiety.

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Omar Hassan

•8M

One thing that really helped me when catching up on back taxes was using Claimyr (https://claimyr.com) to actually get through to an IRS agent. I had tried for WEEKS to get answers about my specific situation and kept hitting automated systems. After using their service, I got through to a real person at the IRS in about 20 minutes who walked me through exactly what I needed to do for my situation. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent I spoke with helped me understand which forms I needed for my specific situation and confirmed that I should focus on the most recent 6 years first. They also flagged that I might qualify for a streamlined procedure since my case wasn't fraudulent - just negligence and procrastination.

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Omar Hassan

•8M

It's actually pretty straightforward - they use a system that navigates the IRS phone tree and waits on hold for you. When they reach a human agent, you get a call connecting you directly. I was skeptical too but it works because they're essentially just handling the hold time for you. The IRS phone number is free, but the problem is the average wait time can be 2+ hours during busy periods, and often they disconnect calls when the queue gets too long. Claimyr just handles that frustrating part of the process so you don't have to keep your phone tied up for hours.

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Diego Vargas

•8M

I need to apologize and correct my previous comment. After my skeptical reply, I decided to try Claimyr as a last resort because I was getting nowhere with the IRS directly. It actually works exactly as described - they called the IRS, waited on hold for about 45 minutes, then connected me once they got a real person. The agent I spoke with was super helpful and explained that in my case, I qualified for a first-time penalty abatement which will save me thousands. Wish I'd known about this service years ago instead of avoiding the problem!

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CosmicCruiser

•8M

In my experience, state tax agencies can actually be easier to deal with than the IRS. The phone wait times are usually shorter, and you can often make an in-person appointment at a local office. Many states do have their own versions of settlement programs similar to the IRS Offer in Compromise, though they might call them different things. For example, California has an "Offer in Compromise" program that's similar to the IRS version, while New York calls theirs an "Offer in Settlement." The qualification requirements and terms can vary significantly by state, so definitely look into your specific state's options.

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