I've been through this exact situation! Missing a payment plan deadline isn't the end of the world, but definitely don't ignore it. Here's what I learned from my experience: First, call the IRS BEFORE your November deadline if possible. I made the mistake of waiting until after I missed mine, which made the process more stressful. When you call, ask specifically about a "payment plan modification" - they have different options depending on your situation. Since you've been making regular payments, you're in a much better position than someone who's been delinquent. The IRS generally views consistent payers favorably. They'll likely offer you a few options: 1. Extend your current plan with a new payoff date (February sounds reasonable) 2. Lower your monthly payments and extend the term further 3. Temporarily reduce payments if you can document the medical hardship The key is being proactive and honest about your situation. Medical expenses are considered legitimate hardship, so mention that specifically. Also, if you have any documentation (medical bills, insurance statements), having those ready can help your case. Yes, you'll continue to accrue the failure-to-pay penalty (0.5% per month) and interest until paid in full, but these are much more manageable than dealing with a defaulted agreement and potential collection actions. Don't panic - the IRS deals with payment plan modifications all the time, especially for people who've been making good faith efforts like you have.

I understand the anxiety you're feeling - I went through something very similar a couple years ago when I couldn't make my final payment due to unexpected car repairs. The stress was overwhelming, but it worked out much better than I expected. Here's what actually happened in my case: I called the IRS about 3 weeks before my deadline and explained my situation. The representative was surprisingly understanding and offered me a few options right on the phone. I ended up extending my payment plan by 4 months with just a $89 fee since I applied for the modification online afterward. The key things that helped my case were: 1) I had made every single monthly payment on time up until that point, 2) I was honest about the unexpected expense, and 3) I called BEFORE missing the deadline rather than after. One tip I wish someone had told me - when you call, ask specifically if you qualify for a "streamlined modification" since you've been compliant with payments. This is faster than a full financial review and often has lower fees. The penalties and interest do continue accruing, but at least for me, the peace of mind of having an approved extension was worth it. And honestly, the IRS representative I spoke with said they much prefer working with people who communicate proactively rather than just disappearing when they can't pay. You've got this - the fact that you're thinking ahead and asking for advice shows you're handling this responsibly!

Adding to the conversation - there's a simple way to remember the main exceptions to the "corporations are exempt from 1099s" rule. I use the acronym FLAMES: F - Fishing boat proceeds L - Lawyer/attorney payments A - Awards/prizes M - Medical/healthcare payments E - Excess golden parachute payments S - Settlements If your payment to a corporation falls into one of these categories, you still need to issue a 1099 even though they're a corporation. Since your CPA firm doesn't fit any of these categories (assuming they're incorporated), they would indeed be exempt.

Great question about CPA firm exemptions! Yes, your CPA firm is likely correct that they're exempt from 1099 reporting if they're incorporated as a corporation. This is one of the most common exemptions business owners encounter. Here's what you should do to stay compliant: Even though they're exempt, you should still request and keep a completed W-9 form from them. This serves as your documentation that they claimed exemption status, which protects you if the IRS ever questions why you didn't issue a 1099 to a vendor you paid over $600. The W-9 will show their business structure and tax classification. If they're a corporation (C-corp or S-corp), they'll be exempt from 1099-NEC reporting for services. The main exceptions where corporations DO need 1099s are payments to medical corporations, attorneys/law firms, and a few other specific categories. For future reference, always collect W-9s from all vendors regardless of whether you think they need a 1099. It's much easier to have the paperwork upfront than to chase it down later during tax season. This way, you'll have proper documentation of everyone's status and can easily determine who needs what forms.

Just to add another perspective here - I've been using Wise for about 3 years and went through this exact same confusion. The key thing I learned is that you need to look at WHERE each currency is actually held, not just that it's a "foreign" company. I contacted Wise support directly and they provided me with a detailed breakdown of which banks hold each currency. My USD was indeed held at a US bank (Community Federal Savings Bank), so that didn't count toward FBAR. But my EUR and GBP were held at European banks, so those did count. The tricky part is tracking the daily balances throughout the year to find your maximum. I ended up creating a simple spreadsheet to track this since Wise statements don't always make it obvious when you hit peak balances across multiple currencies. One more tip: if you're even remotely close to the $10k threshold, it's probably worth filing the FBAR anyway. The penalties for not filing when required are much worse than over-filing when not required. Better safe than sorry with FinCEN compliance.

Based on what you've described, you likely don't need to file an FBAR for your Wise account this year since your maximum balance across all currencies was only around $800. The FBAR filing requirement only kicks in when the aggregate value of ALL your foreign financial accounts exceeds $10,000 at any point during the calendar year. However, there are a couple of important nuances to consider with Wise accounts: 1. **Location matters more than currency**: As others have mentioned, what determines if an account is "foreign" for FBAR purposes is where the financial institution holding your money is located, not the currency type. Your USD in Wise is likely held at a US bank and wouldn't count toward the threshold. 2. **Keep good records**: Even though you're well below the threshold now, I'd recommend tracking your balances more carefully going forward. If you start using the account more frequently for larger transfers, you could potentially hit the threshold without realizing it. 3. **Consider other accounts**: Make sure you're not forgetting any other foreign accounts - even small investment accounts, savings accounts in other countries, or accounts you have signature authority over (like business accounts) all count toward the aggregate total. Since you're nowhere near the $10k threshold with just this account, you should be fine for this year's filing. But definitely keep documentation of your maximum balances just in case!

One thing nobody has mentioned yet is that the rules for Roth IRAs were different when Thiel made his initial contributions back in the late 90s. The income limits were higher relative to top earners' incomes, and some of the current restrictions didn't exist. Plus, the IRS wasn't as focused on monitoring these strategies back then. It's kind of like how some tax loopholes get closed after people start exploiting them widely. The super-wealthy are often the first to identify and use these strategies before they become widely known and potentially restricted.

This is such a fascinating example of how timing and access to opportunities can create massive wealth advantages. What strikes me about the Thiel situation is that it wasn't just about knowing the backdoor Roth strategy - it was having access to pre-IPO shares that 99.9% of people could never get. I've been doing backdoor Roth conversions for a few years now (thanks to the income limits), but obviously I'm buying index funds, not PayPal shares at $0.001 each! It really highlights how the same tax-advantaged accounts can have wildly different outcomes based on what investment opportunities you have access to. The self-directed IRA route sounds interesting but also terrifying from a compliance standpoint. Between the prohibited transaction rules, valuation requirements, and increased IRS scrutiny, it seems like something where one small mistake could cost you way more than you'd save in taxes.

This is a really common issue with family farming operations, and your CPA's questions make perfect sense given the complexity of agricultural tax law. The key distinction here is whether this payment represents compensation, a gift, or some form of ownership distribution. Since you mentioned you've never been an official employee, don't have ownership documents, and this was characterized as a "thank you" from your parents, it most likely should be treated as a gift rather than taxable income. Gifts under $19,000 per person ($38,000 from both parents combined) aren't taxable to the recipient in 2025. However, I'd strongly recommend clarifying a few things with your parents: 1) How exactly they're treating this payment on their farm taxes (deductible expense vs. non-deductible gift), 2) Whether this was truly intended as a no-strings-attached thank you or if they viewed it as payment for your labor, and 3) If there's any pattern of you receiving proceeds from farm sales that might suggest an informal partnership. Your CPA was asking about basis because if you had an ownership stake in the cattle, you'd need to calculate capital gains based on the difference between sale price and your cost basis in the animals. Since you didn't purchase or own the cattle, basis doesn't apply to your situation.

I'm dealing with a similar family farm situation and found myself in the same confusion about gift vs. income classification. What really helped me was getting clarity on the IRS's "substance over form" principle - they look at the actual economic reality of the transaction, not just how the family labels it. A few questions that might help clarify your situation: Was there any expectation that you'd continue helping with farm work in exchange for future payments? Did your parents calculate the $4,300 based on a specific percentage of the sale or was it just a round number they felt was appropriate as thanks? And most importantly, as others mentioned, how are your parents treating this on their Schedule F - as a deductible labor expense or a non-deductible personal expense? If this was truly a one-time thank you with no strings attached and your parents aren't claiming it as a business deduction, then gift treatment makes the most sense. But if there's an ongoing pattern or business-like arrangement, even informal, you might need to consider it differently. The fact that your CPA is asking these questions suggests they want to make sure you're categorizing it correctly to avoid any issues down the road.