Just a heads up, filing an extension for 2016 might be tricky. There's usually a 3-year limit on claiming refunds or credits. You might want to check with a tax pro about that specific year.

Has anyone else noticed that the IRS seems to be even more backed up than usual lately? I've been waiting on a response for months now.

Filing taxes might still be beneficial for you even if you receive SSI and are experiencing homelessness. If you had any income besides SSI during the year (like part-time work), you might qualify for refundable tax credits like the Earned Income Tax Credit, which could result in a refund. SSI benefits themselves aren't taxable income, so you're not required to file if SSI was your only income. However, filing could still be worthwhile if you had any tax withheld from other income sources. As someone experiencing homelessness in Pinellas County, you can get free tax preparation help through VITA (Volunteer Income Tax Assistance) programs. The St. Petersburg Free Clinic and other local organizations offer these services. You don't need a permanent address to file - you can use a shelter address, general delivery at the post office, or even a trusted friend's address. Filing might connect you with benefits you didn't know you qualified for, so it's generally worth checking into, especially when free help is available.

Based on your cousin's situation, I'd definitely go with an Enrolled Agent who specializes in back tax filings and IRS representation. Here's why: 1) The unfiled returns need someone who knows the IRS procedures inside and out 2) The unreported real estate sale has potential capital gains implications 3) Missing W-2s/1099s requires someone familiar with IRS wage and income transcript requests When I was behind on taxes (not 10 years, but 3), I interviewed both a CPA and an EA. The CPA was more expensive and seemed less comfortable with the IRS negotiation part. The EA I ended up hiring had previously worked for the IRS for 15 years and knew exactly how to handle everything. The EA was able to get penalties reduced through a first-time abatement request and set up a reasonable payment plan. Make sure whoever your cousin hires has specific experience with tax resolution and IRS collections, not just routine tax preparation.

Just wanna add something important that nobody's mentioned yet. When your cousin starts filing those old returns, they should NOT use the current year's tax forms! Each year needs to be filed using that specific year's tax forms because tax laws change. I made this mistake when catching up on 3 years of unfiled taxes. I printed the most recent forms thinking they were all the same and had to redo everything. Each tax year has different rules, deductions, credits, and rates. An EA or CPA will know this, but if your cousin tries to DIY any of this, they need to use the correct year's forms which can be found on the IRS website's prior year forms section.

Everyone's talking about whether the IRS will notice, but nobody's mentioned the statute of limitations. The IRS generally has 3 years from the filing date to audit your return (with some exceptions like fraud). So technically, they could "reject" (audit) your return years later. But for a minor discrepancy like yours, they'd typically just send a CP2000 notice (automated underreporter notice) if they catch the mismatch between your reported student loan interest and what the lender reported. You'd owe the tax difference plus maybe some interest, but probably no penalties for something that small and unintentional.

Life pro tip: Always wait until the last minute to file your taxes so you have all your documents! I never file before April 1st to make sure I have all those corrected forms that companies love to send late. Too late for you this year but remember for next time. Student loan companies and investment firms are notorious for sending corrections.

I'm literally going through this exact situation right now. Hadn't filed since 2020 and just got everything submitted last month. Here's what happened: - No jail time (they save that for actual tax fraud not just being behind) - Had to pay about $1,200 in penalties and interest - But I also got back $3,400 in refunds from two of the years - Net positive of $2,200! Just GET IT DONE. The anxiety of not knowing is wayyy worse than the actual consequences. I used a CPA and it cost about $350 per year but worth every penny for the peace of mind.

Make sure you file all the missing years at the same time if possible. I made the mistake of filing one year at a time and the IRS systems got confused - they put a hold on my most recent return because they were still processing my prior years, which delayed everything by months. Also if you do end up owing, ask about a First Time Penalty Abatement. If you've had a clean record before this, they might waive some penalties (but not the interest).