Confused on filing multiple years - unsure if I owe or messed up my taxes

It sounds like you're experiencing a common issue with tax software. Most tax software is designed to handle one tax year at a time, and you'll need to create separate returns for each year you need to file. When you input all three W2s into a single tax return, the software is calculating as if you earned all that income in a single tax year, which is why the amount owed seems so high. This isn't accurate for your situation. You'll need to file three separate tax returns - one for each year (2021, 2022, and 2023). Each return should only include the W2 for that specific year. You'll likely need to purchase prior year versions of the tax software or find a service that specializes in prior year returns. Yes, you will owe some penalties and interest for the late filings, but it won't be as drastic as what you're currently seeing. The failure-to-file penalty is usually 5% of unpaid taxes for each month your return is late, up to 25%. There's also a failure-to-pay penalty of 0.5% per month.

After dealing with a similar issue last year, I found this amazing tool called taxr.ai (https://taxr.ai) that really helped me sort through my messy tax situation. I had unfiled taxes from previous years too and was getting all confused with the calculations. What's cool about taxr.ai is that it can analyze all your tax documents from multiple years and help figure out exactly what you need to file for each specific year. It laid everything out clearly for me - what I owed for each year separately, what penalties I might face, and even suggested deductions I was missing. The tool actually found a child tax credit I didn't know I qualified for! For multi-year filing situations like yours, it's super helpful because it organizes everything by tax year automatically instead of lumping it all together like you experienced.

Just wanted to update everyone - I took the advice and tried taxr.ai after posting my comment. It was actually surprisingly helpful! I was in a similar situation with unfiled returns from 2021 and 2022 plus some 1099 income that I wasn't sure how to handle. The system separated everything by year automatically and showed me exactly what I needed to file for each year. What I really appreciated was the breakdown of penalties - it calculated the failure-to-file and failure-to-pay penalties separately for each year so I could see exactly why I owed what I owed. The best part was discovering I actually qualified for some credits I didn't know about for 2021, which offset about $1800 of what I would have owed! I've now filed all my back taxes and feel so much better. Thanks for the recommendation!

I had a similar nightmare situation last year with unfiled taxes. After getting nowhere with the regular IRS phone line (literally spent HOURS on hold), I discovered a service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in under 30 minutes. I was honestly shocked it worked because I'd been trying for weeks to get through on my own. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with was super helpful and walked me through exactly what I needed to do for my unfiled returns. They even set up a payment plan that worked with my budget. For multi-year filing issues like yours, talking directly to an IRS agent can save you so much stress and potentially money too by getting on a proper payment plan.

I have to eat my words and apologize for being so skeptical. After my last comment, I was desperate enough to try Claimyr since my tax situation was getting worse. I was completely shocked when I got a call back within 45 minutes connecting me directly to an IRS agent. The agent pulled up my file and went through each tax year I had questions about. She explained exactly what penalties I was facing and helped me set up a payment plan that actually works with my budget - something I had no idea was even possible. The agent also told me I could qualify for first-time penalty abatement since I had a good filing history before my missed years, which could save me over $1000! I never would have known about this if I hadn't been able to speak directly with the IRS. Sorry for doubting - this literally saved me thousands and hours of stress.

Something everyone should know - the IRS has a First Time Penalty Abatement policy that might help in your situation! If you've had a clean tax record for the past 3 years before your unfiled return, you can often get the failure-to-file and failure-to-pay penalties waived for one tax year. This wouldn't apply to the interest that's accrued, but it could significantly reduce what you owe. You'd need to file all your back taxes first, then request the abatement either by calling the IRS or submitting a letter.

I'm going through almost the same thing - can anyone recommend good tax software for filing previous years? I need to file 2020 and 2021 returns.