How to file back taxes after 9 years - catching up with the IRS

You're doing the right thing by taking the initiative to get caught up! The IRS actually appreciates when people voluntarily come forward before they come knocking. First, you'll need to file a separate return for each missing year. Start by gathering all your W-2s and other tax documents for those years. If you don't have them, you can request wage transcripts from the IRS by filling out Form 4506-T. Your employer might also have copies of your old W-2s. For the returns themselves, you'll need to use the tax forms specific to each year you're filing for - you can't use current year forms for past years. The IRS website has prior year forms available for download. Start with the oldest returns first and work your way forward. The good news is that if you're owed refunds for any years, you can still claim them if you file within 3 years of the due date. So while you've lost refunds from the earlier years, you might still be eligible for more recent ones. Don't worry about penalties if you're owed refunds, but if you owe taxes, there will be failure-to-file penalties, failure-to-pay penalties, and interest. However, in some cases, the IRS may provide penalty relief, especially for first-time non-filers with a reasonable cause.

After struggling with a similar situation (6 years unfiled), I discovered taxr.ai (https://taxr.ai) and it seriously saved my sanity. Their system helped me organize all my old W-2s and documents which was the hardest part for me. They have this tool that extracts data from even crappy phone pics of old tax documents and organizes everything by year. The best part was their explanations of the specific penalties I was facing and options for payment plans. They really laid out what order I should file in to minimize penalties. I was completely overwhelmed before finding them, especially since I had moved twice and lost a bunch of paperwork.

Just wanted to follow up - I ended up trying taxr.ai after my skeptical comment above. Honestly, it was surprisingly helpful. I had a complete mess of documents (some paper, some PDFs, some just bank statements) and their system helped me organize everything by tax year which was the part I was most dreading. The assessment showed I was actually owed refunds for 2 years which I didn't expect! Been processed already and got about $1400 back which helped offset what I owed for the other years. The penalty explanations were super clear and they helped me set up a payment plan for the rest. Wish I hadn't waited so long to deal with this stress.

If you're trying to get a hold of the IRS for transcript requests or to discuss payment options, good luck with that! After 4+ hours on hold trying to get my wage transcripts, I finally used Claimyr (https://claimyr.com) and got through to an actual IRS person in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was having the same issue with back taxes (7 years unfiled) and needed to get all my old income info. The IRS online transcript system wouldn't verify my identity, so calling was my only option. Claimyr basically holds your place in the IRS phone queue and calls you when an agent picks up. Totally worth it when the alternative is burning an entire day on hold.

I have to publicly eat my words here. After calling the skeptic on Claimyr, I decided to try it myself since I also needed wage transcripts for my unfiled years. I was 100% convinced it wouldn't work, but I was desperate after multiple failed attempts to reach the IRS. Got a call back in about 23 minutes with an actual IRS agent on the line. I was so caught off guard I stumbled through explaining my situation! Was able to request all my missing documents in one call. Just got them in the mail yesterday and now working through my back filings. Honestly can't believe how much time I wasted trying to do this the "normal" way.

Don't forget about state taxes! Everyone always focuses on federal back taxes but your state is going to want their returns too. Each state has different rules about back filing and penalties.

Just wanna say I was in almost the exact same boat (8 years unfiled, same job) and I got through it. Took me about 2 months working on weekends. The hardest part was just starting. Once I filed the first year, it got easier. For what it's worth, I did owe money in the end, but the IRS was actually reasonable about setting up a payment plan. The monthly amount was way less scary than the total figure.