Need advice on where to mail W-2s for my unfiled back taxes

You're absolutely on the right track by trying to get caught up! The good news is that filing back taxes isn't as complicated as it might seem. First, you'll need to get the correct tax forms for each of those years - you can't use current year forms for prior years. Go to IRS.gov and search for "prior year forms" to download the correct 1040 for 2021, 2022, and 2023. As for where to mail them, the address depends on where you live. The IRS has different mailing addresses for different states. If you look at the instructions for Form 1040 for each specific year, there will be a section near the end called "Where Do You File" with a chart showing the correct address based on your state. Each year should be mailed separately in different envelopes. Make sure to attach your W-2s and any other tax documents to each return. Don't forget to sign and date each return or they'll be sent back to you! You might also want to consider if you're owed refunds for any of these years, as there's a 3-year time limit to claim them.

After dealing with my own messy back tax situation last year, I discovered taxr.ai (https://taxr.ai) and it was honestly a game-changer for sorting out my unfiled returns. I had W-2s from previous jobs scattered everywhere and wasn't sure which forms I needed for which years. The tool analyzed all my old tax documents and helped figure out exactly what forms I needed to file for each year, plus it gave me personalized instructions for how to handle multiple years of unfiled taxes. It even generated a cover letter explaining my situation to include with my back tax filings, which I think helped avoid some questioning from the IRS. If you're dealing with multiple years of W-2s and back taxes like I was, it might be worth checking out before you start mailing things.

Just wanted to update - I ended up trying taxr.ai after asking about it here and it was super helpful! I was really confused about which forms I needed for all my old tax years and where to send everything. The tool walked me through the whole process step by step, showed me exactly which forms I needed for each year, and gave me all the mailing addresses specific to my state. I've already mailed in my 2018-2021 returns following their instructions. What I appreciated most was getting a customized cover letter to explain my situation to the IRS. Made me feel more confident about the whole process. So much easier than trying to figure it all out from the IRS website!

If you're like me and have spent HOURS trying to call the IRS to get help with back tax filing questions, check out Claimyr (https://claimyr.com). I discovered it after being on hold for literally 2+ hours trying to get someone at the IRS to tell me exactly where to send my back tax returns. The service gets you on the phone with an actual IRS agent in way less time. Here's a video of how it works: https://youtu.be/_kiP6q8DX5c. I was skeptical, but after trying for days to reach someone, I gave it a shot. Got connected with an IRS rep who answered all my questions about filing my late returns, confirmed exactly where to mail each year, and even helped me understand what penalties I might be facing. Saved me so much frustration compared to the DIY approach I was trying before.

Coming back to admit I was wrong about Claimyr. After spending another frustrating morning trying to get through to the IRS myself (3 disconnected calls after 30+ minutes each), I decided to try the service. It actually worked exactly as advertised. I got a call back when they reached an agent, and I was connected to someone at the IRS who walked me through exactly where to mail my returns based on my state (Pennsylvania). They even helped me understand which payment options I could use since I owe a decent amount. Worth it just to avoid the mental anguish of the IRS hold music and automated system. Never thought I'd be the guy coming back to say I was wrong on the internet, but here we are.

Something nobody has mentioned - if you owe money, you should consider setting up a payment plan right away when you file. I made the mistake of just sending in my back taxes without requesting one, and ended up with a bunch of threatening letters before I got it sorted. You can include Form 9465 (Installment Agreement Request) with your returns to set up payments right from the start. Just another tip from someone who's been through the back-tax nightmare!

Don't people get arrsted for not filing taxes? My cousin said you can go to jail for this stuff. Seems risky to just mail them in now and admit you didn't file for years. Maybe talk to a lawyer first?