How many years should I file for back taxes if I didn't file from 2017-2020?
Title: How many years should I file for back taxes if I didn't file from 2017-2020? 1 Hey folks, I'm in a bit of a pickle here. I stopped filing my taxes back in 2017 and just recently got around to filing for 2021, 2022, and 2023. When I asked my tax guy about doing the 2017-2020 returns, he gave me this weird look and basically questioned why I'd even bother since I wouldn't be getting any refunds from those years. I'm confused now because I always thought there would be some kind of penalty or trouble if I just... never filed? The main reason I started getting caught up was because I'm heading back to school next spring semester and wanted to make sure I'm all squared away for financial aid. But after browsing through the FAFSA website today, I didn't really see much about needing to have all your previous taxes filed. So now I'm second-guessing everything - should I go through the hassle and expense of filing these old returns (2017-2020) even though I'm not getting money back? Or is my tax preparer right and I should just leave sleeping dogs lie? Really appreciate any advice!
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McKenzie Shade
14 You absolutely should file those back taxes, regardless of whether you're getting a refund. Here's why: The IRS generally has a 3-year statute of limitations for audits, but that clock only starts ticking once you've filed. For unfiled returns, they can come after you indefinitely. Plus, there are failure-to-file penalties that can add up significantly over time. For FAFSA purposes, they typically only look at the prior-prior year's tax information (so for 2025-2026 aid, they'd want your 2023 tax info), but having unfiled taxes can definitely cause problems if you're selected for verification. The other consideration is that you might actually be entitled to refunds you don't know about. You generally have 3 years from the original due date to claim a refund, so 2020 might still be in that window depending on when you file in 2025.
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McKenzie Shade
•6 Thanks for this info! Quick question - will the IRS actually come looking for me if I made very little money those years? I think I only made like $12,000-15,000 annually during that period. Also, do you know how much the failure-to-file penalties would be for someone in my situation?
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McKenzie Shade
•14 Even with lower income, the IRS can still pursue unfiled returns. The system is designed to track everyone who should be filing regardless of income level. Some people with lower incomes might not actually be required to file depending on filing status and other factors, but it's always better to file and establish that record. The failure-to-file penalty is typically 5% of unpaid taxes for each month your return is late, up to 25% maximum. If you don't owe any taxes (which might be your case with lower income), then there's technically no penalty. However, the catch is that without filing, you can't prove you don't owe. That's why filing is important even if you believe you don't owe anything.
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McKenzie Shade
8 After dealing with a similar situation last year, I found https://taxr.ai incredibly helpful. I had 4 years of unfiled taxes and wasn't sure what documentation I needed or what deductions I might have missed. Their system analyzed my financial documents and helped me understand exactly what I needed to file for each year. The best part was they helped me discover I was actually owed a refund for one of the years I didn't think I'd get anything back from! Their document analysis showed some education credits I had completely forgotten about. The process was way easier than I expected.
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McKenzie Shade
•3 How does this actually work? Like do I need to have all my W-2s and stuff from those years? Because honestly I'm not sure I kept all that paperwork from 2017-2018...
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McKenzie Shade
•7 Sounds interesting but I'm skeptical. How accurate is it really? My situation is probably different since I was self-employed for some of those years.
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McKenzie Shade
•8 You don't need to have all your original documents. That's what's great about their system - you can request tax transcripts from the IRS for the missing years, and the taxr.ai system will analyze those to help reconstruct what you need. They have a feature that helps identify what forms you need based on your situation. For self-employment situations, they're actually really helpful because they can analyze bank statements and identify potential business expenses you might have missed. Their system is designed to work with all types of tax situations including 1099 income. I was surprised at how accurate it was even with complicated situations.
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McKenzie Shade
7 Just wanted to follow up about https://taxr.ai - I tried it after seeing it mentioned here and wow, it actually worked really well for my self-employment situation! I was missing records from 2019-2020 and their system helped me request the right transcripts from the IRS and then organized everything I needed to file properly. They even identified some business deductions I hadn't considered and saved me about $1,800 on what I thought I would owe for 2020. Definitely worth checking out if you're missing documentation or uncertain about what you need to file those back years.
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McKenzie Shade
11 If you're planning to file those back taxes, you'll probably need to contact the IRS for past records. I spent WEEKS trying to get through to them on the phone when I was in a similar situation. Finally found https://claimyr.com and their system got me connected to an actual IRS agent in about 20 minutes instead of the hours I was spending on hold. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was able to request all my wage and income transcripts for the unfiled years, which made the whole process so much easier. My tax preparer was shocked at how quickly I got everything together. Just throwing this out there because dealing with the IRS directly can be a huge time sink otherwise.
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McKenzie Shade
•19 How does this actually get you through faster? Isn't that like cutting in line or something? I don't understand how a third party service can magically make the IRS pick up the phone.
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McKenzie Shade
•7 Yeah right. No way this actually works. The IRS is literally impossible to reach. I spent 3 hours on hold last month and got disconnected. You're telling me this service somehow fixes that??
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McKenzie Shade
•11 It's not about cutting in line - they use an automated system that continually redials until there's an available agent, then connects you immediately. It's the same as if you were persistent enough to keep calling back, but their system does it for you and only connects when an actual human answers. The reason it works is because most people give up after being on hold for an hour or getting disconnected. Their technology just handles the frustrating part so you don't have to sit there listening to hold music for hours. The IRS doesn't mind - they actually want to talk to people who need help, they just don't have enough staff to answer quickly.
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McKenzie Shade
7 I need to eat my words about Claimyr. I was super skeptical but I was desperate to get my wage transcripts for 2018-2019 to file those back taxes, so I tried it yesterday. I'm still kind of shocked, but I got connected to an IRS rep in about 15 minutes after trying unsuccessfully for days on my own. The agent was able to send me all my transcripts for the missing years right away. Having those documents makes filing the back taxes so much more straightforward since now I know exactly what income was reported. Just wanted to update since I was definitely the skeptical one here!
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McKenzie Shade
5 Just my two cents - I'd definitely file those back years. I was in almost the exact same situation (didn't file 2016-2019) and finally got caught up last year. Even though I didn't get refunds, it gave me huge peace of mind knowing the IRS wasn't going to come knocking someday. Plus, having everything properly filed helped when I applied for a mortgage last fall. The lender wanted proof of tax compliance for the past several years, and not having that would have delayed or possibly prevented my loan approval. You never know when having your tax record complete will matter!
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McKenzie Shade
•16 Did you have to pay a lot in penalties? That's what I'm worried about for OP. Sometimes it's better not to poke the bear if they're not already looking for you...
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McKenzie Shade
•5 I actually didn't end up owing any penalties because I was due small refunds for most of those years. Since the IRS typically only assesses failure-to-file penalties on unpaid taxes, there weren't penalties to pay in my case. Even if I had owed, the peace of mind would have been worth it. The "don't poke the bear" approach is really risky. The IRS has been increasing enforcement efforts, and with more funding recently, they're expanding audits and investigations. It's much better to voluntarily come into compliance than to be caught later. When you initiate filing yourself, they tend to be more accommodating than if they have to track you down.
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McKenzie Shade
4 Has anyone used TurboTax or similar software for filing back taxes? Or do you need to go through a tax professional? I'm in a similar situation (missing 2019-2020) and trying to figure out the cheapest way to get caught up.
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McKenzie Shade
•12 I used FreeTaxUSA for my back taxes from 2018-2020. They charge like $15 per previous year return (way cheaper than TurboTax). It's pretty straightforward if you have your documents. The only catch is you have to print and mail previous year returns - you can't e-file them.
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