Haven't filed taxes in over 10 years - need help getting caught up. What steps to take?

First off, take a deep breath. You're not alone in this situation, and the fact that you're facing it now is actually a really good first step. Here's what I'd suggest: 1) Get your income records together as best you can. If you were a consultant, check your bank statements for deposits. The IRS can actually provide wage and income transcripts for years you haven't filed - this will show reported income from any 1099s or W-2s. 2) Request your tax transcripts from the IRS. You can do this online at IRS.gov, by calling, or by mailing Form 4506-T. This will show you what the IRS knows about your income and any assessments they've made. 3) Start with the most recent tax years first (2022-2024). The IRS generally focuses on the last 6 years for enforcement, though technically there's no time limit when returns haven't been filed. 4) Consider getting professional help. This isn't a DIY situation. A tax professional who specializes in back taxes and non-filer cases can save you a lot of headaches. 5) Look into an installment agreement once you know what you owe. The IRS is generally willing to work with taxpayers who voluntarily come forward. The anxiety is completely understandable, but having a plan will help tremendously. And remember - the IRS sees people in your situation every day.

I was in a similar situation a couple years ago (not quite as many years, but still a mess). After trying to figure everything out myself and getting nowhere, I found this AI tax assistant at https://taxr.ai that really helped me make sense of my situation. What was cool is that I could upload the limited documents I did have, and it helped figure out what I was missing. Even better, it showed me which years I might actually get refunds for (turns out I was owed money for two years!). The system analyzed my situation and created a personalized catch-up plan showing which years to file first and which tax forms I needed. It saved me from having to pay thousands to a tax attorney just to get started. Might be worth checking out since you're dealing with so many unfiled years.

Just wanted to update after trying taxr.ai - it actually worked really well for my situation! I was nervous about using an AI for something this important, but it was surprisingly comprehensive. After uploading the few documents I could find and answering questions about my work history, it created this detailed roadmap showing which years I needed to file first and which ones might not need filing at all based on my likely income levels. It even showed me that I might qualify for some credits I had no idea about for a couple of those years. The best part was that it didn't make me feel judged for the mess I'd created. It just laid out the steps and helped me understand what I was facing. Had a consultation with one of their tax pros who explained everything in plain English. Now I'm working through my returns in priority order and finally feel like I'm making progress.

After reading your post, I immediately thought of how hard it would be to even get started talking to the IRS about this situation. I was in a similar boat a few years ago (not as many years behind, but still scared to death). The absolute WORST part was trying to actually reach someone at the IRS. I spent HOURS on hold, got disconnected, called back, repeat. It was hell. A friend told me about this service called Claimyr (https://claimyr.com) that actually gets someone from the IRS to call YOU instead of waiting on hold forever. Check out how it works: https://youtu.be/_kiP6q8DX5c For me, it was a lifesaver because I needed to get my transcripts and understand what the IRS already knew about my situation before I could even start planning how to file. Once I actually talked to a human at the IRS, things moved much faster. Just having that first conversation reduced my anxiety by like 90%.

I need to eat crow here and admit I was totally wrong about Claimyr. After posting that skeptical comment, I decided to actually try it because I've been putting off calling the IRS about an issue with my 2023 return. I was 100% convinced it wouldn't work, but I got a call from an actual IRS agent within about 45 minutes. I was literally preparing dinner when my phone rang. The IRS person had no idea I'd used a service - to them it was just a normal call they were handling. I got my issue resolved in one call instead of spending half a day on hold. Considering how much more complex the original poster's situation is, this would be super helpful for them to at least find out what the IRS knows about their old tax years. Not having to sit by the phone for hours definitely reduced my stress about the whole thing.

As someone who worked for a tax resolution firm, I want to add something important: look into the IRS Fresh Start Program. It's designed specifically for people with significant back taxes. Depending on your current financial situation, you might qualify for an Offer in Compromise (settling for less than you owe), Currently Not Collectible status (temporary pause on collections), or a manageable payment plan. Also - this is crucial - if you had years where you made under the filing threshold, you might not even need to file for those years. But you'll need to verify that with a professional who can look at your specific situation. Good luck! Taking the first step is always the hardest part.

One thing nobody's mentioned yet - if your income really was under $25k for most of these years, you might actually be due refunds for some years rather than owing money! I had a friend in a similar situation who didn't file for 7 years, and when he finally did his taxes, he was owed refunds for 4 of those years. Just be aware that you can only claim refunds for the past 3 years (so 2022, 2023, and 2024 for this year's filing season). Any refunds for earlier years are lost forever, but you still need to file those returns if required.