9 Is Form 8833 required for all treaty benefits? I thought there were some exceptions where you don't need to file it?

3 You're right that there are exceptions. You generally don't need Form 8833 for treaty-reduced withholding on dividends, interest, royalties, etc. Also, if you're claiming treaty benefits that provide exemptions from tax on certain types of income (like scholarships), you might not need it. But for most substantial treaty positions - especially anything related to your residency status determination, permanent establishment issues, or business profits - you absolutely need it. Better safe than sorry - if you're claiming any significant treaty benefit, I'd recommend filing the form.

10 For 401k, if your employer offers it and you're eligible based on their plan rules, you can generally contribute regardless of your tax status. However, your contribution limit would be based on your U.S. taxable compensation only.

6 How do you know if they're withholding at the right status? My W-4 says married but I'm not sure if they're actually doing it correctly.

10 You can check your paystub - it should indicate the withholding status they're using. Look for something like "Married" or "Single" near the federal tax withholding line. If it doesn't show, ask your payroll department to confirm what filing status they're using for your withholdings. If you want to be extra sure, you can also calculate what your withholding should be using the IRS withholding tables. Compare that to what's actually being withheld from your paycheck. Any significant difference might indicate they're using the wrong filing status.

15 Just a quick correction - the W-4 form no longer uses allowances as of 2020. The form was completely redesigned. Instead of claiming "0" allowances, you would now use Step 2(c) to withhold at the higher single rate, or specify an additional dollar amount on Line 4(c). While getting a refund feels nice, remember that it means you're giving the government an interest-free loan throughout the year. Ideally, you want your withholding to be as close as possible to your actual tax liability - not too much, not too little.

Thanks for bringing this up! Fortunately my wife's insurance is through her employer, not the Marketplace, so it sounds like I won't need to deal with Form 8962. I was worried I'd need to submit both 1095 forms or fill out some additional paperwork to show the transition, but it seems like as long as I can show continuous coverage throughout the year, I should be good.

Exactly, with employer coverage you won't need Form 8962. And just to clarify for everyone reading this thread - the 1095 forms are primarily informational and proof of coverage. You typically don't attach them to your return or enter detailed information from them. For most people with employer coverage, tax software will just ask if you had full-year health insurance coverage, and you'll check "yes." Keep the 1095 forms with your tax records in case there are questions later, but the process is pretty simple.

The individual mandate penalty (for not having coverage) was effectively eliminated starting in 2019 when the penalty amount was reduced to $0. So at the federal level, there's no penalty anymore. But some states like Massachusetts, New Jersey, California, DC, and Rhode Island have their own penalties if you don't have coverage.

Thanks for suggesting H&R Block. I actually tried their free version first before TurboTax, but they also wanted me to upgrade as soon as I entered my 1099-DIV information. Seems like most of the big companies use investments as a trigger for their premium versions.

That's frustrating! These companies are really aggressive with their upselling. Maybe try starting at the IRS Free File page (https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free) instead of going directly to the tax prep sites. Sometimes the versions you access through the IRS have fewer restrictions.

This is actually really good advice! I switched my small investments to a Roth IRA last year and it made my tax filing so much simpler this year. No more reporting tiny dividends and occasional stock sales.

This is EXACTLY what I needed! I found all these screens after following your steps. The key was answering NO to the qualified distribution question but then YES to the after-tax contributions question. FreeTaxUSA is now correctly showing the distribution as non-taxable on my draft 1040. I was stuck in a loop because I was looking in the wrong section entirely. Thank you so much for the detailed steps!

Glad to help! One more tip - save a copy of your Form 8606 each year as documentation of your contribution basis. The IRS can request proof of your contribution history if they ever question the tax-free status of your distributions. This happens more often than people realize with Roth accounts.

I switched from FreeTaxUSA to TurboTax specifically because of IRA distribution issues. TurboTax is more expensive but definitely handles the Roth contribution withdrawals more clearly. They explicitly ask about basis and walk you through the process step by step.