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Ask the community...

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Javier Cruz

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For what it's worth, I'm an academic advisor at a university with lots of veteran students, and this confusion with education credits and GI Bill happens constantly. Two tips that might help: 1) Ask your school's Veterans Affairs office for a "Student Account Summary" that clearly separates GI Bill payments from your out-of-pocket expenses. This documentation is crucial if you ever get questioned. 2) The computer might qualify as an education expense, but you need to prove it was required for your specific program, not just convenient. Some programs explicitly require certain tech specs, which makes this easier to document. Most tax software struggles with the nuances of military education benefits. The default calculations often underestimate legitimate credits.

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Thanks for the tips! Do you know if my school's required materials list would be enough documentation for the computer purchase? My program handbook says students must have a laptop with certain minimum specifications.

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Javier Cruz

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Yes, a program handbook or syllabus that specifically states students must have a laptop with certain minimum specifications is excellent documentation. Save that documentation with your tax records. If your program has that kind of explicit requirement in writing, it significantly strengthens your case for counting the computer as a qualified education expense. Just make sure you're only claiming the portion of computer use dedicated to your education if you also use it for personal activities.

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Emma Wilson

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Just a heads up that education credits are one of the most commonly audited items on tax returns, especially when GI Bill or other education benefits are involved. The IRS system often flags returns where both education benefits AND education credits appear. Make sure you keep ALL documentation for at least 3 years: - Receipts for every qualified expense - Course requirements showing materials were required - Financial aid statements showing what was covered by GI Bill - Statements showing what you paid out of pocket TurboTax isn't necessarily wrong - it's calculating based on the info you provided - but it might not be asking all the right questions to maximize your legitimate deductions.

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Malik Thomas

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I learned this the hard way. Got audited in 2023 for my 2021 education credits while using Post-9/11. The IRS wanted documentation I didn't have anymore and I ended up having to pay back the credit plus interest. Now I scan and save EVERYTHING.

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Avery Davis

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Something nobody's mentioned yet - have you checked if your company has an accountable plan? Some employers have a formal process where they don't "reimburse" expenses but will pay you for them if you follow their documentation procedure. If they do, that might be your best option. Also, see if your manager will at least provide a letter stating that the laptop is required for your job but isn't provided by the company. While it won't make it deductible, it's good documentation to have if your tax situation changes or if you're ever questioned about the purchase.

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Dyllan Nantx

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Thanks for bringing this up - I've never heard of an accountable plan before. I'll check with HR to see if we have something like this in place. That's a really good idea about getting a letter from my manager. Even if I can't deduct it now, having that documentation could be useful later on. I appreciate the advice!

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Has anyone considered just making your employer pay for it? Instead of asking nicely, try framing it as "I need a laptop for the Johnson client visit next Tuesday." Then when they say there aren't enough, say "OK so you're telling me to cancel on the client?" Put it back on them to solve the problem they created.

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This is actually solid advice. I did something similar at my old job - forced management to deal with the consequences of their own policies. They magically found budget for new equipment when client relationships were at stake.

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Omar Zaki

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Make sure to check if the scholarship is covering MORE than just qualified expenses. My son's "full ride" included: - Tuition (not taxed) - Books (not taxed) - Meal plan (TAXED) - Housing stipend (TAXED) - Travel allowance (TAXED) The university just sent him a lump sum for the taxable portions, which got reported on a 1099-MISC. Caught us by surprise the first year when he suddenly owed taxes as a student with "no income"! The taxable portions count as income even though he never saw the money (it went straight to his student account).

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Does the student claim this income on their own return or do the parents claim it if the student is still a dependent?

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Omar Zaki

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The student reports the taxable scholarship income on their own tax return, even if they're still your dependent. It's considered the student's income because they're the recipient of the scholarship. This can create a situation where your dependent student suddenly needs to file their own tax return, even if they don't have a job. In our case, my son had to file his own return for the taxable portion of his scholarship, while we still claimed him as a dependent on our return since we provided more than half his support.

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One thing to check - are you sure the money is actually a scholarship and not a tuition reduction? Sometimes schools call it a "scholarship" but it's technically a reduction in tuition, which has different tax implications. Look at the 1098-T box 5 (scholarships/grants) vs. box 2 (amounts billed for qualified tuition). If it's truly a scholarship and is less than or equal to qualified expenses (tuition, required fees, books for required courses), then it's tax-free. If the scholarship exceeds qualified expenses, only the excess is taxable. My kid got a "presidential scholarship" that confused us at first - turned out it was actually a tuition discount, not true scholarship money changing hands, which affected how we reported it.

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Diego Flores

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Wait this is blowing my mind. My daughter's financial aid letter says "Dean's Scholarship" but now I'm wondering if it's actually a tuition discount. How can I tell the difference? Her 1098-T is confusing me.

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Lara Woods

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Another option nobody mentioned is to check your IRS online account. They've been improving the online services and sometimes have documents available there that aren't in the transcript. Go to irs.gov/account and sign in. Also, if it was interest on your federal tax refund, you can often find this info in your state tax portal too (at least in my state) since they share data about federal refund interest.

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This is half right, half wrong. The IRS account portal is different from the transcript service, but in my experience the Account section actually shows LESS document info than what's in the transcript, not more. The transcript will typically show all information returns including 1099-INT forms. The state tax portal advice is completely incorrect though. States don't have access to federal interest payment information in most cases. This is federal data that isn't typically shared with states in real time.

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Lara Woods

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You're right that there's some overlap between the Account section and transcripts, but they actually do show different information in some cases. For certain years, I've seen information in one but not the other. Regarding the state portal, I should have been more specific - this only applies in certain states that have information sharing agreements with the IRS, and even then it's not universal. In my state (California), I was able to see my federal refund interest payment through the state portal last year, but this was probably because I had to report it on my state return as well. Definitely not a universal solution, but worth checking if other options don't work out.

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Are we overlooking the simplest solution? Can't you just call the IRS and ask them how much the interest was? Even if you don't get the actual form, getting the dollar amount is what you really need, right? I had this issue last year (though not with a 1099-INT) and I just estimated based on my refund amount and how long the delay was. IRS refund interest is like 3% annual rate (adjusted quarterly), so you can ballpark it.

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You're right that the amount is the most important thing. Calling the IRS is definitely an option, but as others have mentioned, the wait times can be really long this time of year. I did take your suggestion to estimate the amount though! Based on my refund (around $4,500) and the delay (about 4 months), I calculated roughly $45 in interest. I'll still try to get the official form or amount, but at least now I have a reasonable estimate if I can't get the actual document before the filing deadline. Thanks for the practical suggestion!

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How to calculate adjusted basis for non-qualified ESPP with 20% stock match - tax implications?

My husband participates in a non-qualified ESPP plan through his employer, and they provide a 20% stock match when he purchases shares (at the same price per share). I'm trying to figure out how to properly handle the tax implications, especially regarding the cost basis. The Settlement Information document shows the cost basis for both the purchased shares and the matched shares. From what I understand, we only pay tax on the matched shares (not the ones he actually purchased), but I'm confused about how to properly adjust the cost basis. I believe the adjusted basis should be the compensation income plus the acquisition cost. For the matched shares, I think the compensation income is the value when they were gifted to him, but what exactly counts as the "acquisition cost" since he didn't directly purchase these matched shares? Should I just use the Fair Market Value at the time he received them? When calculating gains/losses, would I just subtract this FMV from the proceeds? There aren't any fees listed for these transactions. There's also a Supplemental Form showing a cost basis slightly higher than the purchase price, with some gains/losses reported (both short-term and long-term losses). Since these were losses, I'm guessing there wasn't any taxation, but do I still need to adjust the basis as described above? And if there were gains instead of losses, how would I handle the adjusted basis calculation then? Nothing about these shares appears on his W-2. Any help would be greatly appreciated!

Justin Evans

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I've been an investment advisor for years and see this confusion about ESPPs all the time. Another point to consider that nobody's mentioned yet: if you're dealing with losses on these matched shares, make sure you're considering the wash sale rules if you're regularly acquiring new shares through the same ESPP. I've seen clients accidentally trigger wash sales because they sold shares at a loss while continuing to acquire new shares through their regular ESPP contributions. The IRS can be quite strict about this.

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That's a good point I hadn't considered! My husband makes ESPP purchases quarterly. If we sold some of the matched shares at a loss, would the next quarter's acquisition potentially trigger wash sale rules? Does it matter that some are directly purchased and some are matched shares, or does the IRS consider them all the same type of security?

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Justin Evans

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Yes, the next quarter's acquisition could potentially trigger the wash sale rules if it happens within 30 days before or after selling at a loss. The IRS generally considers them the same security regardless of how they were acquired (purchased directly or received as matched shares). What makes this especially tricky with ESPPs is that the acquisition date for new shares is often predetermined by the plan structure, so you can't easily avoid the 30-day window like you might with discretionary investments. Some financial advisors recommend scheduling any loss-harvesting sales carefully around your ESPP purchase calendar to avoid this issue.

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Emily Parker

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Has anyone used TurboTax to handle their ESPP reporting? I'm trying to figure out if it correctly calculates the adjusted basis for matched shares automatically or if I need to override what's on my 1099-B.

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Ezra Collins

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I used TurboTax last year and it didn't handle my ESPP correctly. The software just used whatever basis was reported on the 1099-B, which was wrong for my matched shares. I had to manually override it using the "Adjusted Basis" field and enter my own calculation. It was kind of a pain but worked once I figured it out.

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