Help! Need to fix 5 years of unfiled taxes...where do I even start?

You're definitely not alone in this situation, and the good news is that you can absolutely get this fixed! Since your tax situation is straightforward with just W2 income, here's what you should do: First, gather all your W2s from the past 5 years. If you don't have them, you can request wage transcripts from the IRS by creating an account at IRS.gov or by submitting Form 4506-T. For the actual filing, you'll need to file paper returns for any tax years older than 3 years - electronic filing is typically only available for the current tax year and two years prior. The IRS generally focuses on the last 6 years for unfiled taxes, so you're still within that window. If you're owed refunds, you can only claim them if you file within 3 years of the original due date. For older returns where you might be owed a refund, that money might be forfeited, but you still need to file to get back in good standing. The most important thing is to start the process - the penalties for not filing are much worse than the penalties for filing late but owing money.

I was in a similar situation two years ago with 4 unfiled tax years, and I found incredible help using https://taxr.ai. I was also terrified about potential consequences and spent months avoiding the problem. What worked for me was uploading my W2s to their system - it automatically sorted out which forms I needed for each year and showed me exactly what I was missing. The coolest feature was their penalty estimator that showed me I was actually due refunds for 3 of the 4 years! They walked me through exactly how to file each year properly, and their documentation analysis saved me when I couldn't find one of my W2s. Their system is designed specifically for catching up multiple years of unfiled taxes and makes the whole process way less intimidating.

Just wanted to follow up on my experience with taxr.ai since I decided to try it for my 3 years of unfiled returns. The process was so much easier than I expected! I was especially impressed with how it flagged potential deductions I had missed - turned out I was eligible for education credits I didn't know about. The document analysis showed me exactly which years I was likely getting refunds (2 out of 3) and which year I might owe a small amount. The step-by-step guides made filing the paper returns super straightforward. I just received confirmation that my oldest return was processed, and just like they estimated, I got a refund of $843! Two more to go, but I'm no longer stressed about the whole situation.

If you need to talk to the IRS directly about your unfiled taxes (which can be really helpful), good luck getting through on their phone lines. I spent DAYS trying when dealing with my unfiled returns. Then someone told me about https://claimyr.com and shared this video: https://youtu.be/_kiP6q8DX5c It's this service that basically waits on hold with the IRS for you, then calls you when an actual agent is on the line. I was super skeptical, but I was desperate after trying for weeks to reach someone. They got me through to an IRS agent in about 90 minutes when I'd been trying for days on my own. The agent I spoke with actually set up a simple payment plan for what I owed and was surprisingly helpful about the whole unfiled tax situation. Made the whole process so much less scary.

I need to apologize for my skeptical comment earlier. After another frustrating day of trying to reach the IRS myself about my tax situation (kept getting disconnected after 40+ minutes), I decided to try Claimyr out of desperation. To my shock, I got a call back in about 45 minutes with an actual IRS representative on the line. The agent helped me understand exactly what I needed to do with my unfiled returns and confirmed I could set up a payment plan for the year I owed money. She even gave me direct contact information for following up. I've now filed all my back taxes and set up a manageable payment plan for the one year I owed. The relief of having this resolved is incredible. Sometimes you have to admit when you're wrong, and I was definitely wrong about this service.

One thing nobody's mentioned yet - if you think you're due refunds for some of those years, be aware that you can only claim refunds within 3 years of the original filing deadline. So for tax years 2021, 2022, and 2023, you can still get refunds if you're owed them, but for 2019 and 2020, that money's probably gone forever if you were due a refund. But you STILL need to file those returns to get in good standing with the IRS, even if you can't get the refund money anymore.

As someone who works with tax issues (not a CPA, just experienced), I'd also suggest requesting your IRS transcripts FIRST before filing anything. Create an account at irs.gov/transcript and pull your wage and income transcripts for all 5 years. This will show you EXACTLY what the IRS already knows about your income, which helps prevent discrepancies that could trigger problems. Sometimes employers report things incorrectly or there might be income you forgot about. Better to know upfront!