Haven't filed any taxes since 2021 - what do I need to know for the 2025 filing season?

You're actually in a better position than you might think! Since you've been receiving W-2s and likely had taxes withheld, you might even be due refunds for those years. Here's what you need to know: For past years (2021, 2022, 2023, 2024), you'll need to file the tax forms specific to those years. You can't use current year forms for prior years. You'll need to locate the correct forms for each specific tax year. If you're owed refunds, there's generally no penalty for filing late. However, you can only claim refunds for up to three years from the original due date. So for 2021 taxes (due April 2022), you have until April 2025 to claim any refund. If you owe taxes, then yes, there will be penalties and interest accruing. The failure-to-file penalty is usually 5% of unpaid taxes per month, capped at 25%, plus interest. Filing sooner rather than later will minimize these costs.

After ignoring my taxes for a couple years, I tried taxr.ai (https://taxr.ai) and it made catching up SO much easier. You upload your tax documents like W-2s and 1099s, and their AI system extracts all the information and helps organize everything by tax year. It helped me figure out which forms I needed for each year and made sure I wasn't missing anything important. The best part was it helped me identify some deductions I would have completely missed on my old returns. Since you have all your W-2s saved, it would be perfect for your situation.

Just wanted to follow up - I tried taxr.ai last weekend after seeing it mentioned here, and it was exactly what I needed! I had tax documents scattered across 3 different email accounts and some paper copies in a folder somewhere. The system pulled everything together by year, showed me what I was missing, and even found a 1099 from a side gig I completely forgot about from 2022. Saved me from what would have been an audit nightmare! Definitely recommend for anyone catching up on multiple years.

If you end up owing money to the IRS, you should look into Claimyr (https://claimyr.com). I was in a similar situation last year with 3 years of unfiled taxes and ended up owing a significant amount. I needed to set up a payment plan, but couldn't get through to the IRS after trying for DAYS. Claimyr got me connected to an actual IRS agent in about 15 minutes when I'd been trying for weeks on my own. You can see how it works in their demo video here: https://youtu.be/_kiP6q8DX5c. The agent I spoke with helped me set up a reasonable payment plan that worked with my budget, and the whole process was way less painful than I expected.

I need to apologize for calling Claimyr a scam. I was totally wrong. After struggling to get through to the IRS for almost three weeks (kept getting disconnected after waiting 2+ hours), I was desperate enough to try it. Within 20 minutes, I was talking to an actual IRS representative who helped me set up a payment plan for my unfiled tax years. The amount of stress this removed from my life was incredible. I should have tried it sooner instead of wasting so many hours on hold just to get disconnected. Lesson learned.

Don't panic! I was in your exact situation last year (hadn't filed for even longer - 4 years). Start with the most recent year and work backwards. For all my unfiled years, I ended up getting refunds, so no penalties applied. One important tip: if you have any 1099 income or did any gig work during those years, make sure you track that down too. Those were the hardest documents for me to find.

Quick PSA for anyone in this situation: don't forget about state taxes! When I caught up on my federal returns, I completely spaced on filing the state ones too. Had to go back and do those separately. Each state has their own rules about penalties and interest too.