I went through this exact same situation with my father's estate return two years ago. The IRS kept requesting Form 1310 even though I had already submitted it electronically. After three rounds of back-and-forth, I learned that the issue was actually with how the electronic filing system handles certified documents. Here's what worked for me: I called the IRS number on the letter and asked them to specify exactly what format they needed the court certificate in. Turns out they needed the actual raised seal to be visible, which obviously doesn't transmit well electronically. I ended up having to get a new certified copy from the probate court with clearer certification language and sent it via certified mail with a cover letter referencing the notice number. The whole process took about 10 weeks from start to finish, but once I sent the properly certified documents, they processed the refund without any further issues. Don't give up - it's just a matter of getting them the documentation in the exact format their system requires.

I'm dealing with a very similar situation right now with my late grandmother's return. The IRS sent me the same letter requesting Form 1310 and supporting documents that I know I included with the e-file. Reading through these responses has been incredibly helpful - I had no idea about the raised seal issue with certified documents. That explains why my electronically submitted court certificate might not have been accepted even though it looked fine to me. I think I'm going to follow the advice here and call the IRS number on my notice to ask specifically what format they need the documentation in before I resubmit anything. It sounds like getting clarity upfront about their exact requirements could save weeks of back-and-forth. Has anyone had success getting through to the IRS phone lines recently? I've been dreading making that call because of all the horror stories about wait times, but it seems like that might be the most direct path to resolution.

Has anyone used TurboTax for reporting these CD penalties? Does it handle this situation well or should I be looking at other tax software options?

Just went through this exact situation last month! I had to break my CD early in 2023 for emergency home repairs. Here's what I learned from my research and talking to my tax preparer: The penalty will definitely show up on your 2023 1099-INT (which you'll receive in January/February 2024), not on any amended 2022 form. The bank reports penalties in the year they actually charge them, not when the CD was originally opened. One thing that really helped me was keeping detailed records of the CD closure. I took screenshots of my online banking showing the penalty amount because I wanted to verify it against the 1099-INT when I receive it. The silver lining is that early withdrawal penalties are "above-the-line" deductions, meaning they reduce your adjusted gross income dollar-for-dollar. So if you paid a $500 penalty, that's $500 less in taxable income, which could save you $100+ in taxes depending on your tax bracket. Don't stress too much about it - this is a pretty common situation and the tax treatment is straightforward once you get that 2023 1099-INT!

I had almost the exact same situation happen to me last year! I was organizing a study group event and had to buy pizza and supplies last minute when our department funding got delayed. The university made me fill out a W9 for the $85 reimbursement too. Everyone here is absolutely right - it's just their standard accounting procedure. The W9 doesn't mean you'll owe taxes on it or anything. I was worried about the same thing, but when tax season came around, I didn't receive any 1099 forms for that reimbursement and my tax preparer confirmed it wasn't reportable income since I had all the receipts showing it was a legitimate expense for the university event. The most annoying part was honestly just waiting for the reimbursement to get processed through their system, but the W9 itself was no big deal. Just make sure you keep copies of everything - the receipts, the reimbursement approval, and even the W9 form itself. Universities can be slow with their paperwork sometimes!

I deal with university reimbursements all the time as a graduate student, and everyone here is spot on about the W9 being standard procedure. What I'd add is that you should also ask the university for a receipt or confirmation email once they process your reimbursement - not just for your records, but because it usually states clearly that this was an "expense reimbursement" rather than "payment for services." This documentation can be super helpful if you ever need to prove to the IRS (unlikely, but just in case) that this wasn't taxable income. I keep a folder with all my reimbursement confirmations, and my accountant always appreciates having that clear paper trail showing the difference between actual income and expense reimbursements. Also, don't be surprised if it takes 2-4 weeks for them to cut the check - university accounting departments move at their own pace, but the W9 requirement usually means they're taking it seriously and following proper procedures.

As a US citizen, you absolutely need to report this capital gain on your personal tax return. The fact that your corporation is in the Cayman Islands doesn't shield you from US tax obligations - US citizens are taxed on worldwide income regardless of where it's earned. Since you and your brother likely own more than 50% of this foreign corporation, you're dealing with Controlled Foreign Corporation (CFC) rules. This means you may have had ongoing reporting obligations (Form 5471) even before the sale. The capital gain from selling your shares is definitely taxable as a long-term capital gain since you held them over a year. A few critical things to consider: 1) You may owe taxes on undistributed earnings from prior years under Subpart F or GILTI rules, 2) Don't forget FBAR filing requirements if you had signature authority over company accounts exceeding $10k, and 3) You might also need Form 8938 depending on the value of your foreign assets. I'd strongly recommend getting a qualified international tax attorney or CPA who specializes in foreign corporations. The penalties for getting this wrong can be severe - I've seen cases where people owed more in penalties than the actual tax due. This is definitely not a DIY situation given the complexity of CFC rules and international reporting requirements.

This is exactly the kind of complex international tax situation where you need professional help ASAP. Based on what you've described, you're looking at multiple compliance issues beyond just the capital gains tax. First, yes - you absolutely owe US capital gains tax on the share sale. As US citizens, you're taxed on worldwide income regardless of where the corporation is located or does business. Since you held the shares for 3+ years, it would be long-term capital gains rates. But here's the bigger issue: if you and your brother each own 50% of this Cayman corporation, you've been subject to CFC rules since day one. This likely means you should have been filing Form 5471 annually and potentially paying current US tax on certain types of corporate income even before any distributions. The penalties for missing these filings can be $10,000+ per person per year. You also need to check if you had FBAR filing obligations if you had signature authority over corporate bank accounts exceeding $10k aggregate value at any point. My strong recommendation is to immediately consult with an international tax specialist who can review your entire situation from incorporation to present. You may want to consider the IRS voluntary disclosure programs to minimize penalties if you've missed required filings. This isn't something to handle without professional guidance - the compliance requirements for foreign corporations owned by US citizens are incredibly complex and the penalties severe.

Just to add some practical advice from my experience as a small business owner: Make sure you're keeping VERY detailed records of your business use for any vehicle you're claiming Section 179 on. The IRS looks closely at vehicle deductions. I recommend keeping a mileage log (there are good apps for this) and documentation of business activities conducted using the vehicle. This is especially important if you're using the vehicle for both business and personal purposes, as you'll need to calculate the percentage of business use. Also, if you're on the border with the 6,000 lb GVWR requirement, it might be worth looking for a slightly heavier vehicle just to be safe. My accountant advised me to avoid vehicles that are exactly at 6,000 since there's no wiggle room if the IRS questions it.

Just to throw a wrench in things - has anyone looked into the electric vehicle tax credits instead of Section 179? I was originally going for a heavy SUV for the Section 179 deduction but ended up with an EV truck because the tax credit structure was more beneficial for my situation. With some commercial EVs, you can get up to $7,500 tax credit as a business AND still take depreciation. Haven't seen this mentioned yet but might be worth considering alongside the GVWR discussion.