Has anyone considered the alternative minimum tax (AMT) implications when selling RSUs? I got absolutely destroyed last year because I didn't factor this in when executing my strategy.

One thing I learned the hard way is to also consider your overall income timing when deciding which RSU lots to sell. If you're expecting a bonus or other large income event later this year, it might make sense to realize those capital losses now to offset the higher tax bracket you'll be in. Conversely, if you're between jobs or expecting lower income next year, you might want to hold off on selling the loss lots until you're in a lower bracket where the deduction is more valuable. The $3,000 annual limit on deducting capital losses against ordinary income means timing can really matter for maximizing the tax benefit.

I went through this exact situation last year and learned a few hard lessons that might help you avoid my mistakes. First, when you amend your return, make sure you also calculate and pay any penalties for late payment since the IRS considers fellowship income as earned throughout the year, not just when you file. For entering it in TurboTax, go to Federal > Income & Expenses > Less Common Income > Other Reportable Income. Look for "Other Income Types" and select "Other Income Not Already Reported." Enter your fellowship stipend amount and put "Fellowship" in the description field. One thing nobody mentioned yet - if your fellowship is over $600 and you didn't receive a 1099, you technically should file Form 1099-MISC for yourself (weird, I know). Not everyone does this, but it's technically required. Also, don't forget that you'll owe self-employment tax on the fellowship income since it's not subject to payroll taxes. The quarterly estimated payments you're planning are smart, but calculate them based on your total expected tax liability, not just the fellowship portion. Use Form 1040-ES and remember the safe harbor rule - if you pay 100% of last year's tax liability through quarterlies, you won't owe penalties even if you end up owing more.

I went through this exact same situation during my first year of grad school! You're definitely not alone in being confused - fellowship income is one of those weird tax situations that most software and support staff don't handle well. For TurboTax specifically, here's what worked for me: Go to Federal > Income & Expenses > Less Common Income, then look for "Other Income" or "Miscellaneous Income." There should be an option for scholarship/fellowship income that wasn't reported on a tax form. Enter just the stipend portion (living expenses) as taxable income - not the tuition or fees that went directly to the school. One tip that saved me a lot of headache: contact your graduate school's financial aid office and ask for a "fellowship tax allocation letter." They can break down exactly what portion went to qualified education expenses (tuition, fees, required books) versus your taxable stipend. Most schools can provide this even if they don't automatically issue tax forms. Also, you're absolutely right to plan quarterly payments for 2024! Fellowship recipients are technically considered self-employed for estimated tax purposes, so you'll want to use Form 1040-ES to calculate those payments. It's much easier than dealing with amendments later. The good news is that fellowship stipends are only subject to regular income tax, not self-employment tax, so at least you don't have to worry about that additional 15.3%!

I went through this exact same situation two years ago and can definitely relate to the stress of discovering you've been reporting the wrong basis for multiple years! The consensus here is correct - you really should file amended returns for all three years (2020, 2021, 2022) rather than just correcting it going forward. I know it seems like a hassle, but Form 8606 creates an official paper trail with the IRS for your nondeductible contributions, and having incorrect basis amounts on file will cause problems down the road when you take distributions. One thing I'd add is to make sure you understand WHY your basis calculations were wrong in the first place. Common mistakes include not properly tracking contributions that span tax years (like contributions made in early 2021 for tax year 2020), or incorrectly including rollover amounts in your basis calculations. When you file your 1040-X forms, be very clear in Part III about what you're correcting. Something like "Correcting basis amount reported on Form 8606 for nondeductible IRA contributions" helps the IRS processors understand exactly what they're looking at. The good news is that since you haven't taken any distributions yet, this is purely a record-keeping correction with no immediate tax impact. But getting it fixed now will save you major headaches (and potentially double taxation) in the future.

I went through a very similar situation about 18 months ago - discovered I had been calculating my Form 8606 basis incorrectly for three consecutive years. The stress of realizing the mistake was overwhelming at first, but I can confirm that filing amended returns was absolutely the right path forward. One thing I learned during this process is that the IRS actually appreciates when taxpayers proactively correct these types of errors, especially when no additional tax is owed. In my case, like yours, I hadn't taken any distributions yet, so there was no immediate tax impact. The amendment process itself was more straightforward than I expected. For each year, I filed Form 1040-X with a corrected Form 8606 attached. In Part III of the 1040-X, I wrote something like "Correcting nondeductible IRA contribution basis reported on Form 8606 - see attached corrected form." The IRS processed all three amendments without any issues or follow-up questions. What really helped me was creating a detailed worksheet showing my correct basis calculations for each year, including how the errors carried forward from year to year. This became invaluable reference material when preparing the amendments and will be helpful for future tax filings. Don't beat yourself up too much about the mistake - Form 8606 can be tricky, and basis tracking errors are more common than you might think. The important thing is that you caught it before taking distributions and are taking steps to fix it properly.

Honestly this tax preparer pricing makes me so mad! They're just putting numbers into glorified TurboTax! I used to pay $350+ but switched to doing them myself. Takes an afternoon but saves hundreds.

I'm a tax preparer and wanted to give some insight on the pricing you're seeing. Those quotes ($375-525) are actually very reasonable for your situation. Here's what goes into that cost beyond just "entering numbers": 1. **Business income analysis** - We review all your business expenses, categorize them properly, calculate home office deductions if applicable, and ensure you're taking all legitimate deductions while staying audit-compliant. 2. **Investment transaction complexity** - Long-term stock holdings often involve basis adjustments, dividend reinvestments, or corporate actions that affect your tax liability. Getting this wrong can be costly. 3. **First-time homeowner benefits** - There are several deductions and credits you might qualify for that software doesn't always catch. 4. **Professional liability** - Most preparers carry E&O insurance and will represent you if there are issues with your return. That said, if you're detail-oriented and have time to research, tax software has gotten quite good. Just make sure you understand the implications of each decision, especially around business deductions. A mistake there can trigger an audit or cost you thousands in missed savings.

Don't forget that once you move to Japan you'll need to file Form 2555 for the Foreign Earned Income Exclusion! This is huge - it lets you exclude up to $128,750 (for 2025) of foreign earned income from US taxation if you meet either the physical presence test or bona fide residence test.

I went through this exact situation when I married my Korean spouse! A few additional things to consider that I learned the hard way: If you decide to get your wife an ITIN and file jointly, be prepared for the timeline - it can take 7-11 weeks to get the ITIN, and you might need to file for an extension if you're doing this during tax season. Also, make sure to get certified copies of her passport from the Japanese consulate or use an IRS-authorized Certifying Acceptance Agent in Japan rather than trying to mail original documents. One thing I wish someone had told me: if your wife has any financial accounts in Japan with your name on them (even just as a beneficiary), you might need to report those on Form 8938 (FATCA) in addition to FBAR, depending on the account values. The thresholds are different for overseas residents. Also, since you're planning to move to Japan, start keeping detailed records of your time outside the US now. You'll need this for the Foreign Earned Income Exclusion physical presence test. I use a simple spreadsheet tracking entry/exit dates - it's saved me so much headache come tax time! Good luck with everything, and congratulations on your marriage!