This is such a challenging situation, and I really appreciate everyone sharing their experiences and expertise here. As someone who's been following this discussion, I wanted to add a perspective that might be helpful. The most striking thing about your brother's case is that he actually kept all the physical cash for 35 years - that's almost unprecedented discipline in maintaining records, even if they weren't properly reported. This could actually work in his favor during any disclosure process because it shows he wasn't spending unreported income on lifestyle inflation or hiding assets in complex ways. What concerns me most is the time pressure element that several people have mentioned. Every day he delays increases the risk that some other event (like a banking relationship review, a routine audit, or even a burglary report if someone discovers he has that much cash at home) could trigger IRS attention before he can get ahead of it with voluntary disclosure. From reading all these responses, it seems like the consensus is clear: get a criminal tax defense attorney immediately, understand all available voluntary disclosure options, and create a comprehensive plan before making any deposits or IRS contact. The upfront cost of proper legal representation will likely be a fraction of what poor handling could cost him in penalties, interest, and potential criminal exposure. Has your brother started looking into attorneys yet? Given the complexity and stakes involved, I'd suggest consultations with multiple specialists to make sure he finds someone with specific experience in large voluntary disclosures like this.

This thread has been incredibly informative, and I wanted to share some thoughts as someone who works in banking and has seen similar situations from the financial institution side. When your brother eventually makes this deposit, the bank will absolutely file both a Currency Transaction Report (CTR) and likely a Suspicious Activity Report (SAR). What many people don't realize is that banks have sophisticated software that tracks customer behavior patterns, so even if he had been making smaller deposits over time, the sudden change from zero banking activity to regular cash deposits would have triggered alerts anyway. From the bank's perspective, we're required to ask about the source of large cash deposits. Having a clear, honest explanation prepared (ideally with supporting documentation from his attorney) will make this process much smoother than being evasive or unprepared. One practical consideration that hasn't been mentioned: he should probably open the account at a bank where he doesn't currently have a relationship. This keeps his existing banking separate from what will inevitably become a heavily documented transaction. Also, some banks are more experienced with handling large cash transactions than others - community banks that work with cash-heavy businesses might be more comfortable with the process. The most important thing is that by the time he walks into any bank, he should already have legal representation and a clear disclosure strategy in place. The banking transaction should be the final step in the process, not the first one.

This is all really helpful information! I'm dealing with a similar situation but have one additional question about quarterly estimated taxes. Since I'm treating my eBay selling as a business with Schedule C, do I need to be making quarterly estimated tax payments? My sales have been growing throughout 2024 and I'm worried I might owe a big chunk at tax time. I made about $15K in sales (probably around $8K profit after all expenses), but I haven't been setting aside money for taxes or making quarterly payments. Should I start making estimated payments for 2025, or is there a threshold where this becomes required? I don't want to get hit with penalties, but I also don't want to overpay if it's not necessary for my income level.

One thing I haven't seen mentioned yet is the importance of understanding how eBay's fee structure affects your Schedule C reporting. eBay charges final value fees, payment processing fees, and sometimes listing upgrade fees. All of these are deductible business expenses, but they need to be categorized correctly. The final value fees and payment processing fees would typically go on Line 27a (Other expenses) as "Platform fees" or "Merchant fees." If you use promoted listings or other advertising features, those would go on Line 8 (Advertising). Also, if you're selling in multiple categories on eBay, the fee percentages can vary significantly - electronics might be 12.9% while books could be 15%. This is why it's crucial to download your monthly eBay invoice statements rather than trying to estimate fees. These statements break down exactly what you paid for each type of fee, making your Schedule C much more accurate. I learned this the hard way my first year when I estimated my eBay fees and ended up under-reporting my deductions by almost $400!

Great point about Form 706! I just went through this with my aunt's estate and almost missed that requirement. The estate was just over the threshold at $13.2 million, and none of the consumer tax software I looked at could handle Form 706. One resource that really helped me was the IRS Publication 559 (Survivors, Executors, and Administrators). It's dry reading but explains the difference between estate income and beneficiary distributions pretty clearly. I wish I had read it before starting the 1041 process. Also want to echo the advice about gathering all documents first. I thought I had everything organized but kept finding additional estate expenses weeks later - attorney fees, appraisal costs, even storage fees for estate property. Having to amend a 1041 is not fun and can delay getting the final distributions to beneficiaries. If anyone is dealing with a relatively simple estate (under $100k in income, basic assets), the online software options mentioned here should work fine. But if there's any complexity at all, the peace of mind from using a CPA who specializes in estate returns is worth the extra cost.

I'm currently dealing with my father's estate and this thread has been incredibly helpful! Based on everyone's experiences, I'm leaning toward trying TaxAct Premium first since several people mentioned good results with it. One question I haven't seen addressed - how do these software options handle estimated tax payments for the estate? The estate has been receiving rental income throughout the year, so I'm assuming we'll need to make quarterly payments. Does the software calculate these automatically or do you need to figure that out separately? Also, for those who used professional help, did your CPA handle the entire estate administration or just the tax filing portion? I'm wondering if it makes sense to get professional guidance upfront for the whole process rather than just scrambling at tax time.

Great question and you're being really smart to think through the tax implications upfront! Based on your situation, the gift option is definitely the way to go. Since the car is worth $13,500, you're well under the 2025 annual gift exclusion of $17,000, so no federal gift tax issues at all. You won't need to file any gift tax returns, and your partner won't owe income tax on receiving the car. The fact that she's been making all the payments to you really strengthens your position here - you're essentially just transferring legal title to match who's been the economic owner all along. From the IRS perspective, this isn't really you "giving away" something valuable since she paid for it through you. A few practical tips: - Write up a simple gift letter stating you're transferring the car as a gift with no expectation of payment - Keep records of her payments to you and your loan payments as documentation - Both of you should sign and date the letter For state-level requirements, definitely check with your specific state's DMV. Some states have lower transfer fees for gifts, while others (like California) might still impose use tax even on gifts to non-family members. But the federal tax side should be completely straightforward in your situation. You're handling this the right way by planning ahead!

I went through something very similar last year! The gift option is definitely your best choice here. Since your partner has been making all the payments and the car is worth $13,500 (well under the $17,000 annual gift exclusion), you won't have any federal gift tax issues. What really helped me was understanding that you're not actually "giving away" something of value - you're just transferring legal ownership to match who's been the real economic owner all along. Your partner paid for the car through you, so this is really just paperwork to reflect reality. A few things that made my transfer smooth: - I created a simple gift letter with both our names, car details (make/model/year/VIN), and a clear statement that I was gifting the vehicle with no expectation of payment - I kept copies of all payment records showing the transfers and loan payments as backup documentation - I checked my state's DMV website for any specific gift transfer requirements (some states have reduced fees for gifts) The whole process was much easier than I expected once I had the documentation in order. Just make sure to call your DMV ahead of time to confirm exactly what paperwork they need - it can vary by state. Good luck with the transfer!

Has anyone considered that OP might be confused about what "unearned income" means? Scholarships used for qualified expenses aren't taxable income at all. Only scholarships that exceed your education expenses or are used for room and board are taxable. It sounds like your scholarship was less than your tuition, so none of it should count as taxable unearned income. I think you're getting tripped up by the tax software.

I'm sorry you're dealing with this stressful situation, especially with the family complications involved. Based on what you've described, it sounds like you shouldn't need to file Form 8615 at all. You mentioned you're 20, worked full-time, and provided more than half of your own support. This is key - the "kiddie tax" that Form 8615 addresses doesn't apply to students who are financially independent. The fact that you paid your own rent, groceries, and utilities while working full-time clearly demonstrates you're supporting yourself. Additionally, since your $3,000 scholarship went entirely toward your $8,500 tuition (qualified education expenses), none of that scholarship money counts as taxable unearned income. The software is likely flagging this incorrectly. For your tax software issue, try these steps: 1. Double-check that you marked "Yes" when asked if you provided more than half of your own support 2. In the scholarship/education section, make sure you indicated the full $3,000 was used for qualified education expenses 3. Look for an override option - many tax programs have a way to skip forms that don't apply If the software still won't cooperate, you might need to contact their support or consider switching to a different tax program. You definitely shouldn't need your mother's SSN for this situation, and I'm sorry you're having to navigate tax issues while dealing with family estrangement.