How many years should I file for back taxes to avoid IRS issues?

You should absolutely file those back years, even if you won't get a refund. Here's why: The IRS generally has a 3-year window for you to claim refunds, but they have up to 6 years to audit you (and potentially unlimited time if they suspect fraud or if you never filed). While the 2018 tax year refund window has closed, there are still good reasons to file. For FAFSA purposes, they typically only look at the most recent tax year information, which is probably why you didn't see much about back taxes on their site. However, having unfiled tax returns can trigger other issues: 1. If you ever owed taxes for those years, penalties and interest continue to accrue 2. Unfiled tax returns can complicate mortgage applications, loan approvals, and other financial matters 3. The IRS can eventually file a substitute return for you (which rarely works in your favor) 4. It gives you peace of mind and closure on your tax obligations Your tax preparer probably meant that since the refund window has closed for 2018-2019, there's no financial incentive for you. But compliance with tax law isn't just about getting refunds.

I had a similar situation a few years back and discovered taxr.ai (https://taxr.ai) which was incredibly helpful for catching up on back taxes. Their document analysis tool saved me tons of time trying to track down old W-2s and 1099s from previous years - something my regular accountant was charging extra for. The system actually helped identify some deductions I would have missed for those older tax years, which made filing worth it even though I was outside the refund window for some years. Their tax specialist actually explained that while you might not get refunds after 3 years, filing still protects you from worse penalties and potential IRS actions.

Just wanted to follow up about taxr.ai that I was skeptical about before. I decided to try it for my unfiled 2019 and 2020 returns, and it was actually really helpful. The document analyzer found a business expense deduction pattern across both years that my previous accountant missed. Even though I was outside the refund window for 2019, filing properly reduced what I would have owed if the IRS had created a substitute return. For 2020, I was still within the window and actually got a small refund! The whole process was much less stressful than I expected, and now I don't have to worry about those unfiled years anymore.

If you're trying to reach the IRS to get transcripts or figure out your filing status for those old years, good luck with that! I spent WEEKS trying to get through to a real person. Eventually found Claimyr (https://claimyr.com) and they got me connected to an actual IRS agent in about 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was hesitant at first because it seemed too good to be true, but it saved me hours of redial hell. The IRS agent I spoke with confirmed I needed to file those back years even without refunds since I had some 1099 income they were tracking. They also told me exactly what forms I needed for the specific years, which was super helpful.

Well, I have to eat my words about Claimyr. After my skeptical comment, I decided to try it anyway since I was desperate to talk to someone at the IRS about my unfiled 2018 return. Got connected to an agent in about 20 minutes (which is honestly miraculous compared to my previous attempts). The agent confirmed that even though I couldn't get a refund for 2018 anymore, I still needed to file because I had 1099 income that year. They explained that the IRS computer system had already flagged my account for unfiled returns, and it was just a matter of time before they'd send me a formal notice. By filing voluntarily before that happens, I avoid some of the more aggressive collection procedures. So to the original poster - yes, file those back years! The IRS definitely knows you haven't filed, and it's better to address it proactively.

Something nobody's mentioned yet - if you had very low income during those unfiled years, you might not have been required to file at all. The filing thresholds change yearly, but for example, a single person under 65 in 2018 only needed to file if they made more than $12,000. If you were a dependent during any of those years (like if your parents claimed you), the threshold is even lower. Just something to consider before paying someone to prepare returns that might not be legally required.

Has anyone mentioned the Failure to File penalty yet? It's 5% of unpaid taxes for each month your return is late, up to 25%. If you're more than 60 days late, minimum penalty is either $435 (for returns due after 1/1/2020) or 100% of the tax owed, whichever is less. Since you mentioned 1099 income in your reply, you definitely have unpaid taxes, which means these penalties are already applied to your account in the IRS system. The sooner you file, the sooner you can work on resolving this!