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For those unfiled years, I recommend filing them in order from oldest to newest. We had to file 4 years of back taxes for my father-in-law who had health issues, and doing them chronologically made it much easier to track everything. Also, put each year in a separate envelope! We made the mistake of sending multiple years in one package and it caused confusion at the IRS processing center.
Thank you for that tip about separate envelopes! I definitely would have put them all in one package thinking I was being efficient. Did you receive any kind of confirmation when they received/processed the returns? I'm worried about them getting lost in the mail.
You should definitely send them certified mail with return receipt requested through USPS. That way you'll get confirmation they were delivered. As for processing, it took about 4-5 months before we saw any activity - they're very slow with paper returns. Eventually, we received notices for each return - either bills for what was owed (with penalties) or notices about refunds. If you're really concerned, you can check your husband's IRS transcript online about 6-8 weeks after sending them to see if they show as processed.
Just a heads up - for that 2016 return, if your husband was owed a refund, he's probably out of luck now. The deadline for claiming refunds is generally 3 years from the original due date. So for 2016, that would have been April 2020. But he should still file it! Even if he can't get the refund, having a complete tax history is important for things like mortgage applications, loan approvals, etc.
Yep, this is correct. I worked for a tax firm and we had clients who lost out on thousands in refunds because they waited too long. The 3-year rule for refunds is strict, but the IRS can come after you for taxes owed for much longer!
Something critical that hasn't been mentioned yet - you might need to file an FBAR (Report of Foreign Bank and Financial Accounts) if you have any financial interest in foreign accounts that exceed $10,000 at any point during the year. This includes accounts where you're considered to have signature authority. If you're considered to have an interest in your grandfather's business accounts (which sounds possible given your arrangement), you might need to file this form. The penalties for not filing can be really severe - like $10,000+ for non-willful violations.
Wait, this sounds serious. I don't have signature authority on any accounts in Ecuador, but since I'm sending money and receiving profits, could that count as having a "financial interest"? How would I know if I need to file this FBAR thing?
The definition of "financial interest" can be broad. If you have an arrangement where you're entitled to profits from the business, the IRS might consider you to have a financial interest in the accounts, even without signature authority. The safest approach would be to consult with a tax professional who specializes in international reporting. But generally, if you're investing in a business and receiving returns based on performance, you likely have a financial interest. If the total of all foreign accounts you have an interest in exceeds $10,000 at any point in the year, you'd need to file the FBAR. You might also need to look into Form 8938 (Statement of Specified Foreign Financial Assets) depending on the amounts involved. These are separate from your tax return and have different filing requirements and deadlines.
Curious if anyone knows - would it be better for the grandpa to just label all the money as "gifts" instead of business returns? Wouldn't that avoid all these tax issues?
That approach could create more problems than it solves. The IRS looks at the substance of transactions, not just what you call them. If there's a pattern of you investing money and then receiving returns that correlate with business performance, relabeling them as "gifts" could be seen as tax evasion. While non-US persons can give gifts to US citizens without triggering gift tax for the recipient, unusual patterns of large gifts might trigger extra scrutiny. If audited, you'd need to prove these were genuine gifts with no expectation of return, which contradicts the investment arrangement described.
I actually tried taking loans from my S-Corp last year and got hammered in an audit. Here's what I learned the hard way: If you don't document everything properly with actual loan agreements, repayment schedules, and market-rate interest, the IRS WILL reclassify it as a distribution or compensation. In my case, they treated it as a distribution which meant I had to pay taxes on it anyway, PLUS a penalty for not reporting it correctly. For S-Corps specifically, you also need to be careful about maintaining reasonable compensation before taking any distributions or loans. My mistake was trying to take a "loan" while not paying myself a market salary. Don't mess around with this - do it right or don't do it at all.
What about for a single-member LLC? Are the rules any different since it's a disregarded entity for tax purposes? Could I take loans from my business more easily?
For a single-member LLC that's a disregarded entity, the situation is actually quite different. Since a disregarded entity is treated as the same taxpayer as you for federal tax purposes, technically you can't loan money to yourself - it would be like taking money from one pocket and putting it in another. The business funds are already considered your funds from a tax perspective, so there's no tax advantage to structuring withdrawals as loans. You're already being taxed on the business profits regardless of whether you withdraw the money or not (via Schedule C on your personal return). That said, for proper bookkeeping and to maintain the liability protection of your LLC, you should still document any personal withdrawals properly. If you're mixing business and personal funds without documentation, you risk piercing the corporate veil in legal situations.
Wait I'm confused. So what about these "buy, borrow, die" strategies that billionaires use? Is that completely different from taking money from your business?
Completely different. The billionaire strategy works because they're borrowing from a third party (bank or broker) using assets as collateral. They're not taking money directly from their companies without taxation. When Musk or Bezos get liquidity, they either: 1) Take loans from banks using their stock as collateral (legitimate third-party loans), 2) Sell shares and pay capital gains tax, or 3) Receive salaries/compensation that are taxed as income. The "loan" from your own business isn't actually a loan in the IRS's eyes unless it meets very specific criteria that most small business owners don't satisfy. Otherwise it's just income/distribution with extra steps.
Just a reminder that if you're going to amend your 2020 return, make sure the business expenses you're adding are legitimately deductible. The IRS has been increasing scrutiny on Schedule C deductions lately, especially for tax years 2019-2021 because of all the COVID relief programs. Things like home office deductions, vehicle expenses, and meals/entertainment are particular audit triggers if they seem disproportionate to your business income. Not saying don't claim what you're entitled to - just make sure you have good documentation to back it up!
That's a good point! All of these expenses are legitimate photography equipment (new lenses, lighting, a laptop used only for editing) and documented travel to shooting locations. My business income that year was around $36,000 so the $7,800 in additional expenses isn't out of proportion. Do you think that's going to raise any red flags?
Those expenses sound reasonable given your business type and income level. Photography equipment is clearly a necessary business expense, and as long as your travel was primarily for business purposes and you have documentation (like client contracts showing shoots on those dates), you should be fine. The $7,800 compared to $36,000 in income is a perfectly reasonable ratio for a photography business, which typically has higher equipment costs. Just make sure to categorize everything correctly on your Schedule C - put the equipment under "Equipment" not "Supplies" if it's over $2,500 per item and will last more than a year (might need to be depreciated rather than fully expensed, depending on whether you took Section 179 or bonus depreciation).
Has anyone here experienced an adjustment to their refund amount when amending? I filed an amended return for 2020 because I forgot some 1099 income (opposite problem from OP) and the IRS ended up changing the amount I calculated. Just wondering if this is common.
Giovanni Conti
Here's what my tax accountant told me about this exact situation - you have to separate the academic period from the payment date. The IRS only cares about when money left your hands, not what semester it was for. If you paid in January 2025, that's a 2025 tax year expense, period. Doesn't matter if it was for Fall 2024. Think of it like buying anything else - if you buy something on January 2nd, that's a purchase in that new year, even if you ordered it in December. One thing to watch for next year: if you pre-pay Spring 2026 tuition in December 2025, you CAN claim that on your 2025 taxes! So sometimes you can time payments to maximize credits in a specific year if that helps your tax situation.
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Yuki Yamamoto
β’Thank you for this clear explanation! That makes sense about separating the academic period from when I actually paid. I guess I'll have to wait until next year to claim that big payment. Do you know if there's any limit to how much tuition I can claim next year? Since I'll have both semesters' worth of payments potentially in the same tax year?
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Giovanni Conti
β’You're welcome! For education credits, there are annual limits regardless of how many semesters you're paying for. The American Opportunity Credit has a maximum of $2,500 per eligible student per year, based on the first $4,000 of qualified expenses. The Lifetime Learning Credit maxes out at $2,000, based on 20% of up to $10,000 in qualified expenses. So even with multiple semesters' payments falling in the same tax year, you'll still be subject to these annual limits. What's important is maximizing your eligible expenses up to these limits each tax year. If you have flexibility in when you make payments around December/January, you can sometimes time them to optimize your credits.
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Fatima Al-Hashimi
Don't forget that if your parents claim you as a dependent, THEY would get the education credit based on your expenses, not you! This tripped me up big time last year. If they paid any of your tuition, or if they claim you, make sure you coordinate with them on who's claiming what.
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NeonNova
β’This is such an important point! My parents and I double-claimed education expenses one year and it was a huge headache to fix. You also need to make sure you're not claiming the expenses if someone else paid them.
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