How to file multiple years of back taxes when you haven't filed in years

You're making a smart move by voluntarily filing your back taxes before the IRS contacts you! This shows good faith and can help minimize penalties. For filing multiple years of back taxes, here's what you should know: You'll need to file each year separately using the forms specific to that tax year. Start by gathering all your W-2s and other income documents for each year. 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 only requires you to file the last 6 years, but since you mentioned 9 years, you might want to file them all to be completely clean. Begin with the most recent three years (which are still eligible for refunds if you're owed any) and work backward. You'll need paper forms for previous years since e-filing is usually only available for the current and previous tax year. You can download prior year forms from the IRS website. When you mail them, send each year in separate envelopes and use certified mail so you have proof of filing.

After struggling with a similar situation (6 years unfiled), I found this amazing tool called taxr.ai (https://taxr.ai) that helped me organize all my documents. It uses AI to scan your tax docs and help you figure out exactly what you need for each year. My biggest challenge was finding all my old W-2s and figuring out which deductions I qualified for each year. The taxr.ai system helped extract all the relevant info from the jumbled mess of documents I had and organized everything by tax year. It was so much easier than trying to manually sort through everything myself! They also helped explain which years I should prioritize (the last 3 years where refunds are still possible) and which forms I needed for each specific tax year.

I was really skeptical about using taxr.ai when I first read about it here, but I was drowning in 4 years of unfiled taxes and desperate. I gave it a shot and it was actually super helpful! The system organized all my jumbled tax documents by year and extracted the key information I needed. It even flagged some deductions I would have missed on my own. The best part was that I could still file everything myself using the organized information, which saved me from having to pay a tax pro thousands of dollars. For multiple years of back taxes, having everything organized by year made the whole process way less overwhelming. I still had to do the work of filling out each year's forms, but at least I wasn't staring at a pile of unsorted W-2s and 1099s wondering where to even start.

After trying everything to reach a human at the IRS about my unfiled tax situation, I discovered Claimyr (https://claimyr.com). They got me connected to an actual IRS agent in about 15 minutes when I had been trying for WEEKS on my own. The IRS agent was able to tell me exactly which years I needed to file (turned out I only needed 6 of the 8 unfiled years), which saved me tons of work and stress. They also confirmed I qualified for a payment plan for the back taxes I owed. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was seriously impressed since I'd spent hours on hold before this and never reached anyone. Having that direct conversation with the IRS gave me the exact information for my specific situation.

I was the biggest skeptic about Claimyr and nearly didn't try it. After spending 3+ hours on hold with the IRS multiple times and getting disconnected, I was desperate enough to give it a shot. To my complete shock, they got me connected to an IRS representative in about 20 minutes. The rep pulled up my file and confirmed which specific years I needed to file (saved me from doing 2 unnecessary years) and walked me through the payment plan options for what I would owe. That single phone call saved me so much confusion and probably hundreds of dollars in unnecessary filing work. I'm actually mad I wasted so many hours trying to call myself before discovering this service.

Just wanted to add something important about unfiled taxes that nobody mentioned yet. If you're expecting refunds from any of those years, you only have 3 years from the original filing deadline to claim them. But if you OWE money, the IRS can come after you forever (well, technically there's a 10-year collection statute, but they can reset that in various ways). I'd suggest starting with the most recent 3 tax years to claim any potential refunds, then handle the older ones. You're actually lucky the IRS hasn't contacted you yet! When they caught up with me, they created substitute returns which gave me zero deductions and maximized what I owed. It was a nightmare to correct.

Hav you tried using the free fillable forms on the irs.gov site? For older years you'll need to print and mail them but at least filling them out electronically might be easier. Also dont worry about the penalties too much, the IRS has something called First Time Penalty Abatement that you might qualify for since you haven't had issues before! I did it and they waived about $2,000 in penalties for me.

I went through something very similar about 3 years ago - 7 years of unfiled returns due to some personal struggles. Here's what I learned that might help: First, don't panic about the 9 years. The IRS typically only requires the last 6 years to be filed to be considered "compliant," so you might not need to do all 9 unless you want to be extra thorough. One thing that really helped me was creating a simple spreadsheet to track each year - what documents I had, what I was missing, and the status of each return. It made the whole process feel less overwhelming. Also, since you mentioned money is tight, look into the Volunteer Income Tax Assistance (VITA) program. They offer free tax preparation for people who make under $60,000. Some locations can help with prior year returns too, which could save you hundreds compared to a paid preparer. The fact that you haven't received notices is actually not that unusual - the IRS is incredibly backlogged. But you're absolutely doing the right thing by getting ahead of it. Good luck!