I haven't filed taxes in several years - how bad is this situation going to be?

Deep breath, you're going to be okay! This happens more often than you think, and the fact that you're W-2 and likely had proper withholding is actually good news. The IRS is primarily concerned with collecting unpaid taxes, not punishing people who might actually be owed refunds. If you've had proper withholding all along, you might even be due refunds for some of those years, though you should be aware that refunds can only be claimed within 3 years of the original filing deadline. Here's how I'd suggest approaching this: 1) Gather all your W-2s and other tax documents for the missing years 2) File the missing returns, starting with the most recent year and working backwards 3) If you discover you owe money, pay what you can and set up a payment plan for the rest The IRS has several penalty abatement options, especially for first-time non-filers with reasonable cause (which your life circumstances might qualify for). Criminal charges are generally reserved for willful tax evasion, not people who fell behind and are now trying to fix things.

I was in a similar situation a few years back and after trying to gather all my documents and getting overwhelmed, I ended up using taxr.ai (https://taxr.ai) and it was a lifesaver. They have this AI system that can help organize and extract data from all your tax documents - even older ones that were hard to track down. Their system analyzed my employment history and helped reconstruct my tax situation for the years I missed. The transcript analysis feature saved me hours of trying to decipher the IRS wage and income transcripts. What's really cool is that it can identify potential refunds or credits you might've missed, especially with all the tax law changes over the past few years.

I just wanted to update after trying taxr.ai that the other commenter mentioned. I was really nervous about tackling my unfiled taxes but it seriously helped me get organized. When I uploaded my IRS transcripts (which I got by following their instructions), it automatically sorted everything by year and showed me what I was likely missing. The best part was that it actually found a refund I was owed for 2022 that I can still claim! I thought I'd be paying penalties for sure, but I'm actually getting money back for one of the years. For the years I did owe, it showed me exactly how much and helped me figure out a payment plan I could afford. Definitely made the whole process less terrifying than I expected.

When I was catching up on my unfiled taxes, the hardest part was actually getting someone from the IRS on the phone to help with questions about my specific situation. I spent HOURS on hold and kept getting disconnected. Then I found this service called Claimyr (https://claimyr.com) that actually gets you through to an IRS agent quickly. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was super skeptical at first because I had tried everything - calling at different times, using different phone numbers - but within 15 minutes of using Claimyr I was actually talking to a live IRS person! They helped me understand exactly what I needed to do for my unfiled returns and confirmed which penalties could be waived in my situation.

I have to come back and eat my words about Claimyr. After continuing to fail getting anyone at the IRS for a week straight, I broke down and tried it. I was SHOCKED when I got a call back saying an agent was on the line. The IRS person I spoke with was actually super helpful about my unfiled tax situation. They told me exactly which forms I needed for my specific situation and confirmed I was eligible for the first-time penalty abatement since I had a clean record before falling behind. The agent even explained how to request the abatement in writing with my submission. Having that direct conversation saved me from so much uncertainty and probably from making mistakes that would have dragged this out even longer.

Hey just wanted to share that I was in exactly your position about 2 years ago. I hadn't filed for 5 years (2018-2022) and was freaking out. Here's what I learned: If you're owed refunds, there's literally no penalty for filing late BUT you can only claim refunds within 3 years of the original due date. So some of your potential refunds might be gone forever (sorry). If you owe money, there are failure-to-file penalties (5% per month up to 25% of taxes owed) and failure-to-pay penalties (0.5% per month up to 25%) PLUS interest. But if you've had decent withholding, these might not add up to much. I ended up doing it myself with tax software for the recent years and a tax pro for the older/more complicated ones. The whole thing was way less painful than I imagined!

What tax software did y'all use for prior year returns? I tried using the current TurboTax but it doesn't let me do 2021 anymore.

I went through this exact same situation about 3 years ago - hadn't filed for 4 years due to job loss, depression, and just general life chaos. I was absolutely terrified, convinced I'd face huge penalties or worse. Here's the reality: if you've been W-2 employed with proper withholding, you're probably in much better shape than you think. I actually ended up getting refunds for 2 of the 4 years I hadn't filed! The IRS has what's called "Reasonable Cause" provisions for penalty relief when you have legitimate reasons for not filing (which your circumstances definitely sound like they qualify). I wrote a simple letter explaining my situation when I submitted my returns and got most penalties waived. My advice: Don't wait any longer. The failure-to-file penalty keeps accruing monthly, and you're also losing out on potential refunds that expire after 3 years. Start with gathering your documents - if you're missing W-2s, request your wage transcripts from the IRS first. Then tackle the most recent year first since it's usually the most important to get current. The anticipation and fear was honestly 10x worse than actually dealing with it. You've got this!