How to determine the 6-year period when filing multiple years of back taxes

The 6-year rule isn't quite what you might think. The IRS generally requires you to file returns for the past 6 years if you're trying to get back into compliance after not filing for several years, but there are some important details to understand. First, the IRS can technically go back indefinitely for unfiled returns, but they typically focus on the most recent 6 years. This would mean 2023, 2022, 2021, 2020, 2019, and 2018 (since the 2023 return was due in April 2024). However, if you're hoping to claim refunds, you should know there's a 3-year statute of limitations on refunds. This means you can only get refunds for 2021, 2022, and 2023 at this point. Earlier years' potential refunds are forfeited. For penalty concerns - if you were owed refunds, you likely won't face failure-to-file penalties. Those typically only apply when you owe taxes. But if you did owe for any years, penalties and interest have been accumulating.

When I was catching up on multiple years of unfiled taxes, I found a tool called taxr.ai (https://taxr.ai) that was surprisingly helpful. I had a bunch of old documents and wasn't sure how to organize everything properly for all those back years. What made it useful for me was that it could analyze my old tax documents and help figure out which years I needed to prioritize filing for. It helped me understand which years I was likely due refunds (within that 3-year window mentioned above) and which ones I might owe on. Really saved me from the anxiety of trying to figure all this out manually.

Just wanted to follow up about taxr.ai that was mentioned above. I was skeptical so I decided to try it with my mess of tax documents from previous years. I'm actually impressed - it helped me sort through 7 years of jumbled W-2s, 1099s, and other tax forms I had stuffed in a drawer. The tool showed me that I was still within the window to claim refunds for 2021-2023, and gave me estimates of what I might be owed. I ended up filing those three years first, then worked on the older years to get compliant. Already received my 2021 refund which I thought was long gone! Definitely worth checking out if you're in a similar situation with years of unfiled taxes.

If you're trying to contact the IRS to discuss your specific situation with back taxes, good luck getting through on their phone lines. I spent WEEKS trying to reach someone when I was filing 6 years of back taxes. Then I found this service called Claimyr (https://claimyr.com) which got me connected to an IRS agent in about 20 minutes instead of waiting on hold for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c It made a huge difference because I needed specific guidance about my situation (self-employed for some years, W-2 for others). Getting personalized advice directly from the IRS helped me understand exactly which years I needed to file and the process for submitting multiple years of returns.

I need to eat my words about that Claimyr service mentioned above. After struggling with the IRS phone line for literal days (kept getting disconnected after 2+ hour waits), I decided to try it even though I was sure it wouldn't work. I was shocked when I got a call connecting me to an actual IRS agent after about 30 minutes. The agent confirmed exactly what years I needed to file (last 6 tax years - 2018 through 2023) and explained that for refunds I was only eligible for 2021-2023. They also told me how to submit multiple years of returns at once (don't staple them together, mail them separately but in the same envelope, etc.). Saved me tons of time and confusion. Sometimes it's worth admitting when you're wrong!

Don't forget that for some of those older years, tax software may not be available anymore. I found this out the hard way when trying to file 2018 returns last year. Many of the popular tax programs only keep about 3 years of previous software available. For older returns, you might need to fill out the forms manually or find a tax professional who can access older year software. The IRS website has all the forms available, but it's definitely more work to do them by hand.

Quick question about the mailing process - how do you actually submit 6 years worth of returns? Should I mail them all together or separately? I've heard mixed things.

Just to add another perspective on the 6-year requirement - while the IRS typically focuses on the last 6 years for compliance purposes, the specific years can depend on your situation. If you haven't filed any returns, they generally want 2018-2023 (counting back from when 2023 returns were due). However, if you filed some years but not others, they might focus on just the missing years. Also worth noting that if you had very low income (below the filing threshold) for certain years, you might not have been required to file at all - though you'd miss out on potential refunds like the Earned Income Tax Credit. Given that you mentioned mostly gig work around $25k annually, you were likely required to file (especially with self-employment income over $400), but you probably are due refunds for most years. I'd recommend starting with 2021-2023 since those are the only years you can still claim refunds for, then tackle the older years for compliance. Good luck with getting everything sorted before your mortgage application!