How do I catch up on 5 years of unfiled taxes without getting in trouble?

15 You're in a stressful situation, but take a deep breath! The good news is that for people with straightforward W2 income, catching up on unfiled taxes is actually very manageable. First step: Gather all your tax documents (W2s) for those 5 years. 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. Second: Know that if you're OWED refunds, the IRS generally only allows you to claim them within 3 years of the original filing deadline. So for the oldest 2 years, any refunds may be forfeit - but you still need to file them. Third: If you DO owe taxes, yes, there will be penalties and interest - but the IRS offers payment plans for those who can't pay in full. The most important thing is to file now voluntarily. The IRS is much more lenient with people who come forward on their own versus those they have to chase down. And with just W2 income, you're likely not their primary target for enforcement. Free options: The IRS Free File program can help with current year, and for prior years, you can find fillable forms on the IRS website. Some tax prep services also handle prior year returns, though they may charge for each year.

7 I went through almost the exact same situation last year (6 years unfiled in my case) and was losing sleep over it. I finally found taxr.ai (https://taxr.ai) and it was a complete game-changer for getting through my backlog of unfiled returns. What I found most helpful was uploading all my old W2s and tax documents, and their system organized everything by year and showed me which years I was likely due a refund vs. which ones I might owe on. Saved me from the panic of not knowing what I was walking into. They guided me through filing all the back returns and even handled the communication with the IRS so I didn't have to figure out where to send everything. Best part was seeing that I was actually owed refunds for 3 of the 6 years!

12 Just wanted to update after using taxr.ai from the recommendation above. I finally tackled my 4 years of unfiled taxes last month and the relief is INCREDIBLE. Turns out I was actually owed refunds for 3 of the 4 years, and the system flagged that immediately after scanning my documents. They helped me file everything in the right order and even showed me which refunds I could still claim (the most recent 3 years) and which was too late (oldest year). For the one year I owed, they helped me set up a payment plan that was actually manageable. The whole process was way less scary than I imagined, and now I'm completely caught up. If you're putting this off like I was, seriously just get it done - the stress relief alone is worth it.

8 When I needed to contact the IRS about my unfiled tax situation, I spent DAYS trying to get through on their phone lines. Super frustrating until I found this service called Claimyr (https://claimyr.com). They basically hold your place in the IRS phone queue and call you when an actual human agent is on the line. I was skeptical at first, but you can see how it works in this video: https://youtu.be/_kiP6q8DX5c After trying unsuccessfully for a week to reach someone at the IRS, I used Claimyr and was talking to an IRS agent within about 45 minutes. The agent helped me understand exactly what I needed to submit for my unfiled returns and confirmed I could use the Free File Fillable Forms for my past returns since my situation was simple.

6 Had to come back and eat my words. After posting my skeptical comment above, I was desperate enough to try Claimyr anyway. No joke - I had been trying to reach the IRS for THREE WEEKS with no success. Used this service yesterday afternoon, and by evening I was actually speaking with an IRS representative who walked me through my specific situation with my unfiled returns. The agent confirmed I could still claim refunds for my 3 most recent unfiled years, and explained exactly which forms I needed to file first. They even noted on my account that I was actively working to resolve the unfiled returns so there wouldn't be any surprise enforcement actions. For anyone in a similar situation - the peace of mind from an actual conversation with the IRS is worth every penny. Can't believe I wasted weeks trying to call them directly.

11 Some additional advice from someone who went through this - if you owe money for any of those years, be sure to request an installment agreement right away when you file. The form is 9465 and you attach it to your return. This shows good faith and can help reduce some penalties. I ended up owing about $7,200 for my 4 unfiled years (including penalties) and got approved for a $120/month payment plan. Not ideal but manageable. Also, don't forget about state taxes! Each state has different rules about unfiled returns, so you'll need to handle those separately.

20 Just want to emphasize something important - if you're owed refunds for some years, file those ASAP! The deadline to claim refunds is only 3 years from the original due date. So for example, 2020 tax refunds (due April 2021) can only be claimed until April 2024. If you miss that window, the money is gone forever! Don't leave your own money on the table.