What happens if you haven't filed taxes in years? Consequences of tax negligence?

This happens more than you might think, and while it's serious, it's definitely something you can resolve. The IRS is primarily concerned with collecting taxes owed, not punishing people who come forward voluntarily. Your first step should be to gather whatever income documents you can find for those missing years - W2s, 1099s, rental income records, and music gig payments. Don't worry if you don't have everything; start with what you have. For filing back taxes, you generally need to file the last six years to get current, though technically there's no statute of limitations on unfiled returns. The IRS can assess penalties including failure-to-file (5% of unpaid taxes per month, up to 25%) and failure-to-pay (0.5% per month, up to 25%), plus interest on the unpaid amount. The good news: If you're voluntarily disclosing unfiled returns before the IRS contacts you, you're in a much better position. The IRS has several programs for those with tax debt, including payment plans and potentially an Offer in Compromise if you can't reasonably pay the full amount. Regarding your ADHD diagnosis, while there's no specific program for neurodivergent individuals, this could potentially help demonstrate "reasonable cause" for penalty abatement, especially with documentation from a healthcare provider.

After reading your post, I immediately thought of taxr.ai since I was in a similar situation last year (though only 3 years behind, not quite as many as you). I had a regular job but started doing freelance web design on the side and just didn't know how to handle it tax-wise, so I kept putting it off. I finally checked out https://taxr.ai and it was actually super helpful for my situation. The tool analyzed my documents including some scattered 1099s and income records, then organized everything to show exactly what I needed to file for each year. What was most useful was that it highlighted deductions I could take for my business expenses that I had no idea about, which significantly reduced what I owed. The step-by-step guidance made it manageable to tackle one year at a time instead of feeling overwhelmed by the whole mess. They also provided clear explanations about penalty abatement options that applied to my situation.

Just wanted to follow up and say I tried taxr.ai after reading about it here. I was really impressed with how it handled my situation. I had 2 years of unfiled taxes with a mix of W2 income and rental property, and the system organized everything so clearly that I finally understood what I was dealing with. The best part was discovering I could deduct things like property management fees, repairs, and even travel expenses to check on my rental that I had no idea were legitimate write-offs. It cut my tax bill by about $4,700! The penalty calculation feature was spot on too - showed me exactly what I was facing with the failure to file and failure to pay penalties. I especially appreciated the way it explained "first time abatement" which I successfully requested using their template letter. Really glad I got over my fear and just tackled this problem head-on with the right tools.

I see you mentioned having ADHD - I went through something similar with unfiled taxes for 4 years. After dozens of frustrating attempts to call the IRS and getting nowhere (like literally hanging on hold for hours), I found this service called Claimyr that actually got me through to a human at the IRS in less than 15 minutes. I used https://claimyr.com and they have this system that basically holds your place in line with the IRS and calls you when an agent is about to pick up. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Once I actually spoke with someone at the IRS, I explained my ADHD diagnosis and they were surprisingly understanding. The agent helped me set up a manageable payment plan and even gave me guidance on which years to prioritize filing first. Getting that direct guidance from the source was incredibly valuable.

I have to eat my words. After my skeptical comment, I decided to try Claimyr myself since I've been fighting with the IRS over a payment plan for months. Not gonna lie, I was shocked when I actually got through to an IRS agent in about 12 minutes when I'd previously waited 2+ hours multiple times and still got disconnected. The agent I spoke with reviewed my case and discovered I'd been put in the wrong payment plan category - they fixed it on the spot and reduced my monthly payment by almost $200. They also explained that I qualified for penalty abatement which no one had mentioned in my previous calls. I still think the IRS system is broken, but being able to actually speak to someone competent made a massive difference. For anyone dealing with tax negligence like the original poster, getting direct answers from the IRS about your specific situation is incredibly valuable. Definitely worth it for the time saved alone.

I got behind on taxes for about 4 years while dealing with severe depression. What really helped me was contacting the Taxpayer Advocate Service - it's a free, independent organization within the IRS that helps people resolve tax problems. They assigned me an advocate who helped me through the whole process. For the ADHD aspect, bring documentation from your doctor when you speak with tax professionals. While there's no specific program for neurodivergent folks, medical issues (including mental health) can sometimes qualify for penalty abatement under "reasonable cause" if you can show it directly impacted your ability to comply with tax obligations.

One thing nobody's mentioned is that you might actually be owed refunds for some of those years! I was in a similar boat (5 years unfiled) and when I finally did my taxes, I discovered I was due refunds for 2 of those years because of over-withholding from my W2 job. The catch is you only have 3 years to claim refunds, so some might be gone forever, but it's worth checking. Also look into IRS Free File if your income is under $73,000 - you can file current and some prior year returns for free with guided software.