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StarSailor}

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One thing nobody has mentioned yet - if your cousin is low income, they might qualify for help from a Low Income Taxpayer Clinic (LITC). These clinics provide free or low-cost help to people who make below a certain threshold (generally 250% of the federal poverty line). I volunteered at one during tax season and we helped tons of restaurant workers file multiple years of back taxes. In many cases, people actually got refunds they didn't know they were entitled to! Google "LITC near me" or check the IRS website for locations. They can help with the whole process from filing the returns to setting up payment plans or even negotiating settlements if needed.

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Thank you for mentioning this! Do you know if they help with tip income situations specifically? That's the part my cousin is most worried about.

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StarSailor}

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Yes, they absolutely help with tip income situations! In fact, that's one of the most common issues they deal with for restaurant workers. They can help your cousin figure out how to reconstruct reasonable tip records if they didn't keep detailed logs, and they understand the specific challenges facing tipped employees. The LITC volunteers typically include tax professionals who donate their time and have experience with these exact scenarios. They won't judge your cousin for not filing - their goal is just to help people get into compliance with the least financial pain possible.

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Miguel Silva

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Just to add my experience - I worked delivery for 3 years and didn't file. When I finally did, I ended up getting refunds for all 3 years! Don't assume your cousin will owe a ton. Between the standard deduction (which was around $12,950 for single filers last year) and tax credits they might qualify for, they could be in better shape than you think. Even if they do owe, the IRS is pretty reasonable with payment plans. I know someone who owed about $7,000 and got a plan for like $120/month. Not ideal, but definitely not the financial death sentence people fear.

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How far back can you claim refunds? My boyfriend hasn't filed in like 6 years but he's pretty sure he'd get refunds.

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Miguel Silva

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You can only claim refunds going back 3 years. So for the 2025 filing season, you can claim refunds for 2022, 2023, and 2024. Any potential refunds from years before that are unfortunately lost forever - that's why it's important to file ASAP if your boyfriend thinks he's due refunds! For the older years (beyond the 3-year window), he should still file the returns to get into compliance, but he won't be able to get any refunds from those years even if the calculations show he would have been entitled to them.

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Something else to consider - if you discover an excess contribution, you can actually remove it (plus any earnings on that excess amount) before your tax filing deadline to avoid the 6% penalty entirely. If you've already filed your 2020 return, you might still be able to fix this by filing an amended return. I made an excess contribution to my Roth last year and was able to call my brokerage and specifically request a "return of excess contribution" for the specific tax year. They calculated the earnings on that amount and distributed both back to me. Had to report the earnings as income for the year I received the distribution, but avoided the 6% penalty.

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Thanks for this tip! So if I understand correctly, I could still potentially avoid the penalty even now? My broker is Vanguard - would I just call them and ask for a "return of excess contribution" specifically for my 2020 contribution? Do you know if there's a time limit for doing this correction?

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Yes, you would call Vanguard and specifically request a "return of excess contribution" for tax year 2020. Be very clear about which tax year you're correcting. There is a time limit - ideally you want to do this before the tax filing deadline for that year (including extensions). Since we're well past the 2020 deadline, you'll still owe the 6% penalty for 2020, but removing the excess now stops you from owing the penalty for subsequent years too. The excess contribution continues to be penalized 6% every year until you either remove it or "absorb" it by using up part of a future year's contribution limit.

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Omar Fawaz

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Just to clarify what everyone is saying - yes, you will owe the 6% penalty. The "including 2020 contributions made in 2021" language specifically means the IRS wants you to pretend the money was there on Dec 31, 2020, even though it physically wasn't. I had the exact same situation last year and I used FreeTaxUSA to file. Their software actually has a pretty good walkthrough for Form 5329. Much better than TurboTax which kept giving me errors.

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I second FreeTaxUSA! TurboTax really struggles with Form 5329 and excess contributions. My tax preparer actually recommended I switch to FreeTaxUSA specifically for handling my IRA issues.

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Yara Abboud

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Guys I think there's an even easier solution to this. Most major brokerages provide a supplemental tax statement for RSUs that shows the correct cost basis info that might not be on the 1099-B. Check your documents section on your brokerage account! My company uses Fidelity and they give us a "Supplemental Information" PDF that lists all the RSU income already included on my W-2.

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PixelPioneer

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I checked my E*TRADE account and couldn't find anything like that. Is this something I need to specifically request from them or from my employer?

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Yara Abboud

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E*TRADE should have something similar, but it might be called something different like "Cost Basis Statement" or "Equity Awards Tax Information." Try looking in the Tax Documents section specifically. If you can't find it there, you might need to contact your company's stock admin team rather than E*TRADE directly. Sometimes the employer has to authorize the broker to provide that supplemental information. For anyone who can't find this document, an alternative is to look at your last December paystub or your W-2, find the total RSU income reported there, and match it to your vesting statements to calculate the proper basis yourself.

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I just want to add that this cost basis issue is super important to fix correctly. I messed this up two years ago by not adjusting the $0 basis on my 1099-B and ended up paying tax TWICE on about $8,000 of RSU income - once as income and again as capital gains. Had to file an amended return to get my money back!

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Paolo Rizzo

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Did you have to pay penalties when you filed the amended return? I'm in the same boat and just realized I messed up last year's taxes.

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7 Don't forget you can also file an extension! Form 4868 gives you until October 15 to file, though you still need to PAY what you estimate you owe by April 18. I'm a freelancer too and I often file extensions because I'm waiting on K-1 forms from investments. It gives me time to find the right tax pro rather than rushing with whoever has availability.

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22 How do you estimate what you owe if you don't have time to do the calculations? That's the part that confuses me about extensions.

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7 You make an educated guess based on last year's return and your current situation. The simplest method is to look at what you paid last year, then adjust up or down based on whether you earned more or less this year. You want to pay enough to avoid underpayment penalties. Another approach is to do a rough calculation using your 1099s and W-2s, estimating major deductions but not worrying about getting everything perfect. It's better to slightly overpay and get a refund later than underpay and face penalties. Just make sure to submit the payment with your extension form by April 18th.

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11 I was in your EXACT situation 2 years ago and I just walked into H&R Block with no appointment. They assigned me someone on the spot and I filed that day. It was more expensive than I wanted ($380) but the peace of mind was worth it. Just bring ALL your docs and they'll handle it.

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19 Did they actually save you money compared to TurboTax though? I've heard mixed things about H&R Block for anything complicated.

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Something important nobody has mentioned yet: even if you don't owe any federal taxes, you might want to file anyway because you could be eligible for the Earned Income Tax Credit (EITC) depending on your exact income and situation. This is a refundable credit meaning you can get money back even if you didn't have taxes withheld. The threshold for singles without children is lower, but still worth checking. There are also education credits if you're in school part-time. Don't just assume you shouldn't file because your income is low - sometimes that's exactly when you SHOULD file to claim refundable credits!

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I actually am taking some community college classes! Would that qualify me for education credits even though my income is low? Also, what's the income range for that Earned Income Tax Credit thing you mentioned? This makes me think I definitely should file even though the tax place told me not to.

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Yes, education expenses could qualify you for the American Opportunity Credit or the Lifetime Learning Credit! The American Opportunity Credit is partially refundable, meaning you could get up to $1,000 back even if you don't owe taxes. You need Form 1098-T from your school which shows your tuition payments. For the Earned Income Tax Credit, a single person with no qualifying children needs to earn less than about $17,640 in 2025, and be at least 25 years old (with some exceptions). Since you're 19, you might not qualify for EITC yet unless you meet one of the exceptions, but the education credits are definitely worth looking into. This is exactly why general advice like "don't bother filing" can sometimes cause people to miss out on money they deserve!

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I'm a payroll specialist and just want to mention - this isn't technically an I-9 issue. The I-9 is for employment eligibility verification (citizenship/work authorization). What you're describing is a W-4 issue. The W-4 is the form that tells your employer how much federal tax to withhold. But yes, like others said, if you're making under the standard deduction ($13,850 for 2025), you won't owe federal income tax anyway. Just make sure to submit a new W-4 so they start withholding correctly going forward!

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Sayid Hassan

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Oh that makes sense why they were confused when I mentioned the I-9! I just knew it was some form with a letter and number lol. Is there a way I can check if my W-4 is filled out correctly before submitting a new one? I don't wanna mess it up again.

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