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Ask the community...

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I think everyone is missing an important point here - you could potentially reclassify this as paying for educational expenses directly! The IRS allows you to pay for qualified education expenses for someone else without it counting toward the gift tax limit if you pay the educational institution directly. Next time, maybe send the money straight to the college instead of the family?

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Amina Bah

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But I already sent the money to the family directly. Is there any way to reclassify it now? And does this educational expense exception work for schools in other countries too? The college is in Malaysia.

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Unfortunately, you can't reclassify it after the fact. The money has to be paid directly to the qualified educational institution at the time of payment to qualify for the educational expense exception. For foreign educational institutions, they generally do qualify for this exception as long as they're a legitimate educational organization. The school doesn't have to be in the US for the direct tuition payment exception to apply. But again, the key is that the payment must go straight from you to the school - not through the family first. Keep this in mind for any future assistance you might provide.

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Sorry to jump in late, but I work in tax preparation and wanted to add something important: even though you can't deduct this as a charitable contribution, make sure you're tracking all your actual eligible donations for the year! A lot of people don't realize they can only benefit from itemizing deductions if their total deductions exceed the standard deduction ($14,600 for single filers in 2025).

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Omar Hassan

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Which tax software do you recommend for keeping track of charitable donations throughout the year? I always scramble at tax time trying to find all my receipts.

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Frustrated: Can ANY tax software handle purchasing I-bonds with my refund via Form 8888?

I'm pulling my hair out trying to find a tax program that will let me use my refund to buy I-bonds using Form 8888. I've tried FOUR different services and none of them work for this! The IRS Free Fillable forms seemed promising until I discovered it won't even print the Form 8888, and according to their user guide, if it doesn't print, it won't be sent. Great. TaxSlayer wanted me to pay upfront before I could even see if it supported the forms I needed. Hard pass. TaxHawk seemed decent until I got to the refund section - it only lets you designate direct deposit accounts, nothing for savings bonds! Cash App Tax (formerly Credit Karma) was the worst experience. Had to jump through ridiculous hoops just to get started - downloading a mobile app, scanning QR codes, the works. They demanded excessive details for every 1099, way more than legally required. Then after all that - surprise! - they also only support direct deposit for refunds, no I-bonds. What infuriates me is how these companies advertise "all the forms you need" when they clearly don't. For simple things like Schedule B, all you legally need is the bank name and interest amount - not addresses, phone numbers, and federal IDs that these programs demand! Same with IRA distributions - you just need the total amount from all accounts, not individual breakdowns. I'm about ready to give up and mail in paper forms, but then my refund will take an extra six weeks. I intentionally arranged for a larger refund specifically to buy I-bonds with it, so that's six more weeks of lost interest. Can anyone recommend a free or reasonably priced tax software that DEFINITELY supports buying I-bonds with your refund through Form 8888? I need someone who has actually done this successfully, not just assumptions!

Dananyl Lear

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Another option nobody's mentioned yet is TaxAct. I've used it for the past three years to buy I-bonds with my refund and it works perfectly. Their Premium version is usually around $40-50 for federal (depending on when you file), which is way cheaper than TurboTax. The Form 8888 option appears in the "Refund" section after you've completed your return. You can specify exactly how much you want to allocate to I-bonds and how much to direct deposit. One tip: make sure the name on your tax return EXACTLY matches what you want on the bond. The IRS is super picky about this. If your name is "Robert" but you go by "Bob", use "Robert" on both your return and the bond section.

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Does TaxAct force you to enter all those extra details for interest and dividends that the OP was complaining about? I hate when tax software asks for info that isn't actually required on the real forms.

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Dananyl Lear

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TaxAct does ask for the payer names for interest and dividends, but it doesn't require all the excessive details like addresses and phone numbers. You can just enter the name and amount for each 1099-INT or 1099-DIV. For IRA distributions, you do need to enter each 1099-R separately, but that's actually correct since the distribution codes can be different. It's much less demanding than some of the other software I've tried.

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Ana Rusula

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This is exactly why I went back to using an accountant! I tried the DIY route for years and kept running into these exact limitations. Software companies design their products for the most common scenarios and anything slightly unusual gets overlooked. I know paying an accountant seems expensive compared to software, but mine charges $275 and handles everything - including splitting my refund between direct deposit and I-bonds. No frustration, no wasted weekends, and I actually end up with BIGGER refunds because he finds deductions I didn't know about.

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Fidel Carson

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Does your accountant e-file for you? I'm wondering if they have access to better tax software than what's available to regular consumers.

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Carmen Ruiz

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Check if your state has a cap on how much assessed value can increase year-over-year. In my state, there's a 3% cap for primary residences. If your assessed value jumped that much in one year, it might actually be illegal depending on your local laws. Also, make sure you're getting all the tax breaks you're entitled to. When we bought our house, we had to specifically apply for the homestead exemption - it wasn't automatic. That saved us about $800/year. And definitely file that appeal ASAP!

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Zara Malik

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I had no idea about these caps! I'll definitely look into that for our state. Do you know if these exemptions are something we can apply for retroactively? We bought in 2022 but never filed for any exemptions because we didn't know about them.

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Carmen Ruiz

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In most places, you can apply for exemptions like homestead retroactively, but usually only for the current tax year and maybe the previous year. It varies by location though. When you call your assessor's office, specifically ask about retroactive applications for exemptions. Also, if this is your primary residence and you've lived there since you purchased in 2022, make sure the county knows that. Sometimes they assess at a higher rate if they think it's a rental or second home. Just having the property correctly classified can make a big difference in your tax bill.

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one thing nobody mentioned yet - check if the previous owners had any special exemptions that fell off when you purchased. my parents had a senior exemption that saved them about $900/yr, so when i bought their house my taxes went up by that amount even though the assessed value stayed the same. its worth asking the county if thats what happened in your case.

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Good point. When I bought my house, the previous owner was a veteran with a disability exemption. My taxes were way higher than what they had been paying, but there was nothing wrong with the assessment itself. Just the exemptions changing.

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Zara Malik

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That's really interesting and something I hadn't considered. The previous owners were an older couple who had lived there for about 15 years, so they might have had some exemptions we don't qualify for. I'll definitely ask about this when I contact the assessor's office!

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One thing nobody has mentioned yet is that you need to check your 1099-B from your broker carefully! Often they don't include the correct cost basis for RSUs and you'll need to make an adjustment on your tax return. Most brokers will show a cost basis of $0 for RSUs or an incorrect amount, which means you'll need to manually adjust this on Form 8949 by checking box "B" and entering code "B" in column (f) to indicate that you're correcting the cost basis. Then you enter your actual cost basis (FMV at vesting). This is a super common issue that trips up a lot of people with RSUs.

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That's really helpful - I just checked my 1099-B and you're right, the cost basis shown is way off! So I need to use Form 8949 and check box "B" to make this correction? Do I need to include any supporting documentation with my return to explain the adjustment?

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You don't need to include any additional documentation with your return to explain the adjustment. The IRS is familiar with this situation for RSUs. Just make sure you keep records of your RSU grant documents, vesting schedules, and the fair market value on vesting dates in case you're ever audited. When completing Form 8949, you'll enter the information from your 1099-B in columns a through e, then in column f enter code "B" (for basis adjustment), and in column g enter the difference between your correct basis and what's reported on the 1099-B. This effectively adjusts the basis to the correct amount for calculating your gain or loss.

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NebulaNinja

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I made a horrible mistake with my RSUs last year that cost me thousands. I didn't realize the 1099-B was wrong and just entered everything as-is in my tax software. I basically paid tax twice on the same income - once when it vested (on my W2) and again when I sold the shares because the cost basis was wrong. If anyone else has already filed with this mistake, you can file an amended return (Form 1040-X) to fix it and get a refund. I did this and got back about $2,300 in taxes I shouldn't have paid.

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Javier Gomez

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How far back can you amend returns for this kind of mistake? I think I might have done the same thing for the past 3 years 😬

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Mei Zhang

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For calculating self-employment taxes, don't forget about the Qualified Business Income deduction (Section 199A)! As a self-employed person, you might qualify for up to a 20% deduction on your qualified business income. This is separate from your regular business expense deductions on Schedule C. Also, if you didn't make estimated tax payments last year, look into the "safe harbor" provisions when you file. If your previous year's tax liability was covered through withholding (from your job before getting laid off), you might qualify for reduced penalties or even avoid them altogether depending on your situation.

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Can you explain more about the QBI deduction? I thought that was only for certain types of businesses. Does it apply to all self-employed people regardless of what service they provide?

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Mei Zhang

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The QBI deduction applies to most self-employed individuals, sole proprietors, partnerships, and S corporations. There are some limitations if you're in certain "specified service trades or businesses" like health, law, accounting, etc., and if your income is above certain thresholds (around $170,500 for single filers in 2022). For most freelancers making under that threshold, including graphic designers, you'll likely qualify for the full 20% deduction on your business profits. The calculation gets more complex at higher income levels or for certain professions, but tax software usually handles this automatically. It's basically free money that reduces your taxable income (though it doesn't reduce self-employment tax), so definitely don't miss out on it!

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has anyone used quickbooks self employed? im in same boat freelancing first time and behind on everything. was told it tracks mileage and expenses automatically + helps w quarterly estimated payments going forward?? not sure if worth $15/mo or whatevr they charge

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I've used QuickBooks Self-Employed for 2 years and it's pretty good for the basics. The mileage tracker works well if you remember to use it. The quarterly tax estimator is helpful but sometimes feels a bit off. The expense categorization is decent but you still need to review everything.

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