How do I start filing taxes after not filing for multiple years?

First, congratulations on getting to a better place and deciding to address this issue. That's a huge step and deserves recognition. The good news is that if you had enough taxes withheld from your paychecks, you might actually be owed refunds for some years. The IRS generally has a 3-year deadline for claiming refunds, so while some earlier years might be lost, you may still be able to recover money from more recent years. For unfiled returns where you might owe money, there's no statute of limitations until you file, but the fact you haven't heard from the IRS suggests your withholding might have covered your tax liability. Since you worked W-2 jobs with withholding, they likely have records of your income even without your filed returns. Here's where to start: 1. Gather all your tax documents (W-2s, 1099s, etc.) for all unfiled years. If you don't have them, you can request wage transcripts from the IRS. 2. Consider using a tax professional - look for an Enrolled Agent (EA) or CPA with experience in unfiled returns. Most offer free consultations where they can give you a cost estimate. 3. You can also check if you qualify for the IRS Voluntary Disclosure Program, which can sometimes reduce penalties. The IRS is generally more interested in getting people back into compliance than punishing them, especially if you voluntarily come forward before they contact you.

I was in a similar situation a few years back (different reasons, but 4 years of unfiled taxes). After trying to gather all my documents and getting overwhelmed, I found this AI tax service called taxr.ai that really helped me organize everything. Their system analyzed all my messy tax docs and gave me a clear picture of what I needed to file for each year. The thing that helped most was their transcript analysis tool that showed exactly what the IRS already knew about my income each year. It helped me prioritize which years I needed to file first and which ones might actually result in a refund. I could see which years I'd likely owe money on and which I might get money back. Check them out at https://taxr.ai if you're struggling to organize everything. Their system helped me avoid missing any income that the IRS already knew about (which would have triggered bigger problems down the road).

Just wanted to follow up - I ended up trying taxr.ai after commenting here and wow, it actually delivered. I was surprised how much it simplified the process of figuring out what income the IRS already knew about. For my situation (5 years unfiled with work in multiple states), it showed me that two of the years I'd actually be getting refunds, which I didn't expect! I still hired a CPA to do the actual filing (as the service suggested), but having everything organized first saved me a ton of money. The CPA estimated it would have cost about 30% more if she had to sort through all my documents from scratch. The visualization of what income was reported each year and what I might owe vs. get back was super helpful for budgeting the whole catch-up process.

If you need to talk to the IRS directly about your situation (which might be necessary), be prepared to wait on hold FOREVER. After three attempts and waiting over 2 hours each time, I gave up and used Claimyr (https://claimyr.com) to hold my place in line. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was honestly shocked when they called me back with an actual IRS agent on the line. I was able to get a complete accounting of which returns they were expecting from me and whether they had already created substitute returns (which is what happens when you don't file). The agent was actually pretty helpful in explaining what I needed to do to get back in good standing. If you're serious about fixing your tax situation, you'll probably need to speak with the IRS at some point. This saved me from wasting an entire day on hold.

I owe everyone here an apology, especially the person who recommended Claimyr. I was so skeptical I decided to try it myself just to prove it was BS, and I'm eating my words now. After months of not getting through to the IRS, I had an agent on the line within 2.5 hours (without me having to actually be on hold). The IRS agent confirmed I had unfiled returns for 3 years, but surprisingly, they hadn't started collections yet because they calculated I'd be due refunds based on my withholding. The agent gave me direct instructions on which forms to file and in what order, plus noted on my account that I was voluntarily coming into compliance. For anyone else in a similar situation - don't be stubborn like me. Getting actual information directly from the IRS about your specific situation is invaluable, and waiting on hold for hours isn't necessary.

One thing nobody mentioned yet - make sure you're addressing both federal AND state taxes. Each state has different rules about how far back you need to file and penalties for late filing. I was in a similar situation (4 years unfiled) and got federal sorted out only to get blindsided by my state tax authority, which was actually much more aggressive than the IRS. Check if your state has a voluntary disclosure program too - many do.

I went through this after 7 years of not filing. Here's what surprised me: for most of those years, I was actually owed refunds! I ended up getting money back for 3 of the 7 years, even after penalties. Since you mentioned having maximum withholding, you might be in a similar situation. I used TurboTax for the more recent years and a CPA for the older, more complicated ones. Cost me about $1200 total for professional help with 4 years, which was worth it for the peace of mind. Don't panic about criminal charges - those are extremely rare and typically only happen in cases of deliberate fraud or extremely high dollar amounts. The IRS mainly wants compliance and their money.