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As someone who works at a university financial aid office, definitely check if your college has a VITA (Volunteer Income Tax Assistance) program! Many schools offer free tax prep help for students, and they can often help with back taxes too. Our campus VITA program has accounting students supervised by professors who help with exactly these situations. Also, once you file your back taxes, look into an IRS payment plan. The basic installment plans let you pay as little as $25-50 per month depending on what you owe, which is WAY better than ignoring it and having them eventually garnish your wages or put liens on your property.
Thanks for mentioning VITA! I had no idea my school might offer that. Do they help with multiple years of back taxes though? And do you know if I need to make an appointment or can I just walk in during tax season?
Most VITA programs can help with back taxes, especially for relatively straightforward situations like yours. They typically handle the current tax year plus previous years. The IRS provides VITA volunteers with training for handling back tax returns. You'll definitely need to make an appointment, especially for multiple years of taxes. These services get extremely busy during tax season. I'd recommend calling your university's financial aid or student services office now to find out when their VITA program starts accepting appointments for the 2025 filing season. Some programs start booking as early as January, and slots fill up quickly!
Lucas Turner
If you do end up owing a significant amount, don't panic! The IRS has several payment options: 1) Short-term payment plan (120 days or less) with no setup fee 2) Long-term payment plan with affordable monthly payments 3) Offer in compromise if you can prove financial hardship I ended up on a payment plan paying $120/month for two years and it was totally manageable. Just make sure whatever you agree to is something you can consistently pay.
Kai Rivera
ā¢One thing to add - if the amount you owe is under $10,000 and you can pay it off within 3 years, the IRS generally automatically approves payment plans. You can set it up online without even having to talk to anyone.
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Just a heads up that if your HELOC was used for anything other than home improvements, you might not be able to deduct the interest at all. The Tax Cuts and Jobs Act changed the rules starting in 2018. I learned this the hard way after using mine for college expenses.
Owen Jenkins
ā¢Oh crap, I didn't even think about that. My HELOC was mainly used for kitchen and bathroom renovations, but I did use about $10k of it to consolidate some credit card debt. Does that mean I can only deduct part of the interest?
Yes, you would only be able to deduct the portion of interest that corresponds to the home improvement expenses. The IRS expects you to track this and allocate the interest accordingly. For example, if 80% of your HELOC was used for the renovations and 20% for credit card debt, you could only deduct 80% of the interest paid. You'll need to keep good records showing how the money was used in case of an audit.
Has anyone successfully e-filed an amended return? Last time I had to do this (back in 2020) I had to mail in a paper return and it took FOREVER to process.
Isaac Wright
ā¢Yes! I e-filed an amended return through TurboTax last year and it was processed in about 12 weeks. Way better than the 16+ months my paper amended return took during COVID. Most tax software supports e-filing 1040-X forms now.
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One tip from my experience with reasonable cause penalty relief - make sure you emphasize that you're normally compliant with tax obligations. When I called about my medical-related penalty, the agent specifically asked if I had a history of filing and paying on time. When I confirmed I'd never had issues before this, they seemed to consider that a strong point in my favor. Also, be ready to explain what steps you took to try to meet your obligations despite your circumstances. In my case, I mentioned that I attempted to file electronically but couldn't complete the process due to my condition, and tried to get help but couldn't find anyone available on short notice.
Should I mention that I actually did try to file through a relative but they messed it up? My situation was similar - I was hospitalized for 2 months and asked my brother to handle my taxes, but he completely forgot until after the deadline.
Yes, definitely mention that you took reasonable steps by asking your relative to help. That shows you recognized your tax obligation and actively tried to meet it despite your hospitalization. Explain that you delegated this responsibility while you were unable to handle it yourself, which demonstrates your intent to comply. Make sure to emphasize that you made what you believed was a reasonable arrangement given your medical situation, but circumstances beyond your control still prevented timely filing. The IRS is generally understanding when you can show you made good faith efforts to comply despite serious limitations.
I called about a first-time penalty abatement last year when I had surgery complications that prevented me from filing. The whole call took maybe 15 minutes. The agent just asked when my surgery was, how it affected me, and if I had filed late before (I hadn't). She approved it right on the spot! Has anyone used any tax software that makes this process even easier?
TurboTax has a feature that helps identify if you qualify for penalty abatement and gives you guidance on requesting it. I used it last year after missing a deadline due to a family emergency, and it made the process pretty straightforward.
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Amara Okafor
Another option is to check if your brokerage offers any summary reports. Robinhood specifically has a "tax summary" section in their tax documents that gives you consolidated numbers you can use. For crypto, they should provide a summary of proceeds and cost basis for all transactions. If you're reporting everything on FreeTaxUSA, you can often just enter the summary totals rather than each individual transaction. Look for the line items on your 1099-B that show total proceeds and total cost basis for short-term and long-term transactions separately.
AstroAce
ā¢I found the summary page on my Robinhood statement but I'm still confused about one thing. Some of my trades are marked as "covered" and others as "uncovered" - do I need to separate these when entering them into FreeTaxUSA?
Amara Okafor
ā¢Yes, you should separate covered and uncovered transactions when entering them into FreeTaxUSA. "Covered" means your broker is reporting the cost basis to the IRS, while "uncovered" means they're not (usually for older securities or ones transferred from another broker). FreeTaxUSA will have separate entry sections for covered vs. uncovered transactions. The tax calculation is the same, but the IRS wants them reported separately because they can verify the covered transactions against what your broker reported, while uncovered transactions are based solely on your records.
If you have a lot of trades, don't try to enter them one by one! I made that mistake last year with about 40 trades and wasted hours. Three options that worked for me: 1. Use the summary totals from your 1099-B (usually on the last page) 2. Use FreeTaxUSA's bulk entry option where you can enter multiple similar transactions at once 3. If your brokerage offers a CSV or Excel download of your transactions, you might be able to use that to organize things before entering
Do you know if FreeTaxUSA allows you to import a CSV file directly? That would save so much time compared to manual entry.
GalaxyGlider
Has anyone successfully used the "summary method" instead of transaction-by-transaction reporting for wash sales in TurboTax? My broker provides a summary with total proceeds, cost basis, and wash sale adjustments that matches their 1099-B totals.
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Malik Robinson
ā¢I tried that last year and it worked great! Just go to the investment income section, choose "Enter on my own" instead of import, and select the summary option. As long as your 1099-B has the summary totals clearly stated (Box 5 on most forms), this satisfies IRS requirements.
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GalaxyGlider
ā¢Thanks! That sounds much easier than trying to reconcile hundreds of individual transactions. My broker's 1099-B does have clear summary totals in Box 5, so I'll try this approach. Would be so much simpler than spending hours trying to figure out why specific wash sale calculations don't match.
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Isabella Silva
Don't forget to check if you have any wash sales that happened in December 2024 where you repurchased in January 2025! These span tax years and are especially tricky. TurboTax sometimes handles these correctly while your broker might not include them on this year's 1099-B.
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Connor O'Brien
ā¢Omg this might be exactly what's happening! I did sell some losers in late December and then bought back some positions in January when I got my bonus. So TurboTax might actually be correct and my broker's 1099-B could be missing these cross-year wash sales?
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Isabella Silva
ā¢Exactly! This is a common situation that causes these exact discrepancies. The IRS wash sale rule definitely applies across tax years, but brokers can only report transactions that occurred within the calendar year on your 1099-B. So if you sold at a loss on December 28, 2024, and repurchased on January 5, 2025, that's 100% a wash sale according to IRS rules. Your broker might not flag it on your 2024 1099-B because the repurchase happens in the next reporting year. TurboTax, however, is correctly looking at your full transaction history across the year boundary and applying the wash sale rule properly. In this case, TurboTax's calculation would be the correct one to use on your tax return!
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