Haven't filed my taxes in 4 years - Should I be worried about jail time?

You're not going to jail for this situation, so take a deep breath. The IRS generally reserves criminal prosecution for people who are deliberately evading large amounts of taxes or committing fraud. Since you had withholding from your W-2 employment, you're likely in a much better position than you think. If you're owed refunds for any of those years, there are no penalties for filing late when the IRS owes YOU money. However, you can only claim refunds within 3 years of the original due date, so you might have lost some money for the oldest year. If you do owe for any years, there will be penalties (failure-to-file penalty of 5% per month up to 25% of taxes owed, plus failure-to-pay penalties and interest), but nothing that should be financially devastating given your income level. The best approach is to file all your back taxes ASAP. You might want to look into using a tax professional who specializes in back taxes, but you don't need a lawyer for this situation.

I was in almost the exact same situation as you last year (hadn't filed for 5 years, regular W-2 income around $65k). I was panicking about it until I discovered taxr.ai (https://taxr.ai) which helped me sort through all my documents and organize everything I needed. It saved me so much stress because I could upload all my old W-2s and other documents, and it extracted everything automatically so I didn't have to manually input years of data. The tool basically separated everything by tax year and showed me exactly what I needed to report for each one. I was also worried about penalties but it helped estimate what I might owe or get refunded before I actually filed. Made the whole process way less intimidating.

Just wanted to follow up - I decided to try taxr.ai after my initial skepticism and I'm honestly shocked at how helpful it was. Uploaded all my old W-2s and 1099s last weekend and it organized everything by year automatically. Turns out I'm actually owed about $3,700 in refunds for the last 3 years (though I lost out on the 4th year since it was too old). The site helped me see exactly which forms I needed for each year and gave me confidence to finally file everything. Already submitted 2023 and 2022, working on the rest this weekend. Such a relief to be getting this handled finally!

When I had a similar situation a few years back, the hardest part was actually getting through to someone at the IRS to confirm what documents they had on file for me before I filed. I spent DAYS on hold trying to reach them. I eventually used https://claimyr.com which got me connected to an actual IRS agent in about 20 minutes instead of waiting for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Basically they wait on hold with the IRS for you and call when they have an agent on the line. Getting that conversation with the IRS changed everything because I found out they actually had some forms reported for me that I had completely forgotten about. Saved me from submitting incomplete returns that would have just created more headaches.

I have to eat crow on this one. After my skeptical comment I decided to try that Claimyr service myself since I needed to ask the IRS about a notice I got. I figured it wouldn't work and I'd just waste a few bucks, but holy crap, I actually got a call back in about 35 minutes with an IRS agent on the line. The agent was able to tell me exactly what years I had unfiled returns according to their system and what information they had on file for my income. Huge weight off my shoulders knowing exactly what I'm dealing with now. I still have to do the work of filing everything, but at least now I know what I'm up against.

Just to add some perspective from someone who's been through this: I didn't file for 6 years (2009-2014) and finally got everything squared away in 2015. Here's what happened: 1) For the years I was owed refunds, I got them (except for the ones past the 3-year limit) 2) For the years I owed taxes, I had to pay penalties and interest 3) I set up a payment plan for what I owed 4) Life went on and everything was fine NO JAIL TIME. No scary agents showing up at my door. Just some paperwork and eventually a monthly payment that was totally manageable. The anxiety of not filing was WAY worse than actually fixing the problem.

Has anyone else noticed that tax filings for previous years require using old tax forms? I just went through catching up 3 years of taxes and got confused because the forms change slightly year to year. Make sure you're using the correct year's forms and tax software when you file! The IRS website has previous years' forms but it can be confusing to navigate.