Has anyone used TurboTax for AMT calculations with stock options? I heard it doesn't handle the AMT credit carryforwards correctly and I'm worried I'll mess something up. Would I be better off with H&R Block or going to a CPA?

I went through a similar situation last year with ISOs and AMT, and I wish I had understood the mechanics better beforehand. Let me try to fill in some gaps that might help you. The key thing to understand about your $143,000 ISO exercise is that the "bargain element" (difference between what you paid and fair market value) gets added back as an AMT preference item. So if you exercised options with a strike price of $10 and the shares were worth $20, that $10 difference per share becomes AMT income even though it's not regular taxable income until you sell. With your $187,000 salary plus the ISO adjustment, you're definitely going to be in AMT territory. The good news is that your mortgage interest is still mostly deductible under AMT (unlike state taxes), and your charitable deductions will help both calculations. One thing that helped me was using the AMT Assistant worksheet from IRS Publication 909 to do a rough calculation before year-end. It's not perfect, but it gave me a ballpark figure. The key is understanding that you'll likely owe AMT this year, but you'll generate AMT credits that can be recovered in future years when your regular tax exceeds AMT. For planning purposes, if you still have unvested options, consider the timing of future exercises more carefully. Spreading them across multiple years can help minimize the AMT impact compared to doing large exercises all at once.

The residency test is indeed a major hurdle that many people overlook. Since your parents are in Thailand, you're unfortunately correct that you likely can't claim them as dependents due to the residency requirement. However, don't give up entirely on tax relief. As Mateo mentioned, you might still be able to deduct medical expenses if you pay providers directly. This means instead of sending money to your parents who then pay the doctors, you would need to pay the Thai medical facilities directly from your US bank account. Keep detailed records of these direct payments. Another option to explore is whether any of the medical care qualifies as qualified medical expenses that you could pay with a Health Savings Account (HSA) if you have one. While the dependency rules are strict, HSA rules for medical expenses can sometimes be more flexible. I'd strongly recommend consulting with a tax professional who specializes in international tax situations before your next filing. The rules around foreign medical expenses and dependencies are complex and change frequently, so getting expert guidance could save you from costly mistakes.

I've been following this discussion and wanted to share some additional considerations for your situation. Given that Thailand doesn't meet the residency test for claiming dependents, you might want to explore whether restructuring how you provide support could help. One approach is setting up direct payment arrangements with the medical providers and caregiving services in Thailand. This creates a clearer paper trail and potentially stronger documentation for any deductions you might be able to claim. You could also consider whether any portion of the expenses might qualify under other tax provisions - for instance, if you're providing financial support that could be characterized differently. Another angle to consider: if your parents have any US-sourced income or if there are ways to establish a stronger connection to US tax obligations, this might open up different options. Some taxpayers in similar situations have found success by having their parents file US tax returns even when not strictly required, which can sometimes help establish the relationship needed for dependency claims. The key is comprehensive documentation regardless of which approach you take. Keep records of all transfers, medical bills, provider contracts, and any correspondence with medical facilities. Even if current tax law doesn't provide the relief you're hoping for, tax regulations do change, and having thorough documentation will position you well for any future opportunities.

The Kill-A-Watt meter approach mentioned by @GalacticGladiator is brilliant and probably the most cost-effective solution! I'm definitely going to try this. One thing I'm still wondering about though - for those tracking business vs personal miles, what's the best way to handle trips that are mixed purpose? Like if I drive to a client meeting but also stop at the grocery store on the way back, how do you allocate that? Do you just count the miles to/from the client and ignore the grocery store detour, or is there a more precise way to handle it? Also, @Mateo Rodriguez, your point about being locked into actual expenses vs standard mileage is really important. I hadn't realized that choice in the first year was permanent. Given that my EV is relatively new and expensive, I'm thinking actual expenses might be better initially, but I should probably run the numbers with my accountant to be sure.

This has been such a helpful discussion! I'm dealing with the same situation and the Kill-A-Watt meter solution seems perfect for my needs. Just ordered one on Amazon. One additional consideration I haven't seen mentioned - make sure to check if your state offers any EV tax incentives that might affect your deduction calculations. Some states have rebates or tax credits for EV purchases or charging equipment that could impact how you handle the business expense portion. Also, for anyone using apps to track mileage, I've found that setting up automatic triggers (like when you arrive at certain business locations) makes it much easier to maintain consistent records without having to remember to log every trip manually. The point about being locked into actual expenses vs standard mileage in the first year is crucial - definitely something to discuss with your tax preparer before making that decision!

One thing nobody has mentioned yet is that the Tax Cuts and Jobs Act changed some rules that might affect your 1256 contract loss carryback. If your losses include any from after December 31, 2017, there could be transition rule complications. The TCJA didn't eliminate the 1256 contract loss carryback period, but some of the interaction with other tax provisions changed. Double check if your 2018 losses were from transactions before or after the cutoff date.

I went through something very similar with my 1256 contract losses from futures trading in 2018. The IRS initially rejected my carryback attempt, and it turned out I had made two critical errors: First, I didn't properly complete Part IV of Form 6781 for the carryback year. You need to show the carryback amount in line 11 and make sure the math flows correctly through to Schedule D. Second, and this was the big one - I failed to include a clear election statement with my amended return. The IRS wants to see explicit language stating that you're electing to carry back the 1256 contract losses under Section 1212(c). I had to write something like "Taxpayer elects to carry back $[amount] of net capital losses from Section 1256 contracts from tax year 2018 to tax year 2017." After I resubmitted with these corrections plus all the supporting documentation everyone else mentioned (both years' Form 6781, detailed calculation statement, etc.), it went through without any issues. The whole process took about 8 months from start to finish, but I eventually got my refund. Check your rejection letter carefully - they usually give you at least a hint about what specific item they couldn't locate or verify in your filing.

Had my appointment last month and honestly it wasn't as scary as I thought! The agent was actually pretty nice and walked me through everything. Main things they asked: confirm SSN, previous addresses from last 3 years, and details about my 2023 tax return. Whole thing was done in 45 mins including wait time. Pro tip: bring a bank statement too - they asked for it to verify my direct deposit info for the refund.

Been through this twice now and it's really not that bad! First time I was super nervous but the IRS staff were actually helpful. Make sure to bring originals of everything - they need to see the actual documents, not copies. Also arrive 15 mins early because they're pretty strict about appointment times. The questions are mostly just confirming info from your tax return and previous addresses. Good luck @Mateo - you've got this!