Help! I haven't filed taxes in 6 years - where do I even start?

Ok, first of all, take a deep breath! This is fixable. Many people fall behind on filing for years, and there are clear steps to get back on track. Start by gathering all your tax documents for those years - W-2s, 1099s, unemployment statements, etc. If you don't have them, you can request wage transcripts from the IRS by creating an account at IRS.gov or using Form 4506-T. The IRS generally focuses on the last 6 years for unfiled returns, so you'll need to file for all those years. You're right that you can only paper file for older returns. You'll need to download the correct year's forms from the IRS website since each year has different tax laws and rates. The Fresh Start program can help with payment plans once you've filed. And yes, if you had withholding in years you would have received refunds, those can potentially offset years where you owe. This is called "offsetting," but you need to file all returns first so the IRS can make this calculation. I'd recommend starting with the most recent year (2023) and working backward. Don't try to do all 6 years at once - that's overwhelming. Just tackle one return at a time.

After falling behind on 5 years of taxes (mostly self-employed income), I was completely stuck like you. I finally used https://taxr.ai to help organize all my documents and figure out what I needed for each year. Their AI analyzed everything I had and identified what was missing. It even helped reconstruct some missing income records by analyzing my bank statements. The hardest part was getting started, but their system walked me through each year separately and explained what forms I needed for each situation (W-2 employment, 1099 work, unemployment benefits, etc). They even helped me understand which deductions I could still claim for those old returns.

Just wanted to follow up - I finally tried https://taxr.ai after putting it off for weeks because of anxiety. What a relief! I had 4 years of unfiled returns and was missing half my documents. The AI helped me figure out exactly what I had, what I was missing, and how to get replacement documents for each year. It was super helpful for my unemployment year since I had lost that 1099-G form. The system helped me calculate what I likely received based on my state's benefit formulas and some bank deposits I had. Turns out I was actually owed refunds for 3 of the 4 years! Just mailed in all my paper returns last week and already feeling so much better about the whole situation.

After trying to get through to the IRS for weeks about my unfiled returns, I finally tried https://claimyr.com and got through to an actual IRS agent in about 15 minutes! You can see how it works here: https://youtu.be/_kiP6q8DX5c I was skeptical at first, but I was desperate after calling the IRS dozens of times and never getting through. The IRS agent was able to tell me exactly which years I needed to file, confirmed which years they already had records for, and helped me set up a payment plan for what I owed once I got everything filed. They also told me about the Failure to File penalty (which increases the longer you wait) and how to request penalty abatement through a First Time Penalty Abatement if you've had a clean compliance history before this.

I need to apologize for my skeptical comment. After waiting on hold with the IRS for 2+ hours yesterday and getting disconnected AGAIN, I broke down and tried the Claimyr service. I honestly can't believe it, but I got connected to an IRS representative in about 45 minutes. The agent helped me understand exactly which years I need to file (they only required the last 6 years even though I was behind by 8), and explained how I could request abatement of some penalties since I had a legitimate hardship during part of that time. They also confirmed that my withholding from more recent years could potentially offset some of my older tax debts once everything is processed. I feel like I have a clear path forward now after YEARS of anxiety about this. Sometimes it's worth paying a little to save your sanity.

Free advice from someone who went through this: DO NOT just start filing the most recent year without a plan! I made that mistake and it triggered automated notices for all the missing years at once. Instead, gather ALL your documents first, then prepare ALL the returns, then mail them in TOGETHER with a brief explanation letter. That way the IRS processes everything as one case rather than flagging you multiple times. Also, don't forget your state tax returns! Each state has different rules for back filing, and some have more aggressive collection practices than the IRS.

Has anyone here actually used the "Fresh Start" program? My tax preparer mentioned it but then wanted to charge me $3000 to help with my unfiled returns. Seems like a lot when I'm already struggling financially.