Is this something that employers automatically withhold or is it something you have to pay at tax time? I'm getting close to that range with all my overtime this year.

Employers are supposed to automatically withhold the Additional Medicare Tax once your wages exceed $200k for the year. However, there's a quirk: if you have multiple jobs or your spouse works and you file jointly, your combined income might exceed the threshold even if no single employer pays you over $200k. In that case, your employers won't withhold the extra 0.9%, and you'll need to either make estimated tax payments or be prepared to pay it when you file. You can also request additional withholding on your W-4 to cover it. It caught me by surprise because I had two jobs last year that together put me over the threshold.

This is really important. I live in California and the state brackets have even more dramatic jumps than federal. My overtime last year pushed me from 8% to 9.3% state tax bracket and it definitely took a bite out of those extra earnings.

Oh no, I didn't even think about reporting my Japanese bank accounts! I had about $15,000 in my account before I moved everything to the US. Is there a deadline for filing this FBAR form? Is it the same as the tax return deadline?

The FBAR deadline is April 15, but it automatically gets extended to October 15 if you miss the April deadline. You don't need to request the extension specifically for the FBAR. The form is filed electronically through the Financial Crimes Enforcement Network's BSA E-Filing System, not with your tax return. It's fairly straightforward - you just need to provide information about each account, including the maximum value during the year, account number, and the financial institution's information.

Adding to this - I had the same experience but also found that e-filing with the Foreign Tax Credit form went much smoother than paper filing. Paper filing with international forms seems to trigger more manual reviews and longer delays.

Does FreeTaxUSA handle multiple 1099s well? I have like 8 different clients who sent me 1099-NECs this year.

Absolutely! I had 12 different 1099-NECs last year and FreeTaxUSA handled them with no problem. You can enter them all individually or combine them on your Schedule C - it gives you both options. The software also lets you categorize different types of income if you have multiple business activities, which was really helpful for me since I do both consulting and some product sales.

I've actually tested three different options side by side the last two years (TurboTax, FreeTaxUSA, and TaxAct). The federal refund/amount owed was identical in all three when I entered everything correctly. But I noticed TurboTax was much better at prompting me for deductions I might have missed.

Is this actually legit though? Seems like you're just trying to find a loophole that would get flagged in an audit. Can you really just "decide" your commute is now your business?

It's not about "deciding" your commute is your business - it's about actually establishing a legitimate business purpose that happens to use your commute route. My brother-in-law's commute photography project generates actual income through print sales, and he has documentation showing the business purpose of each trip. You'd need to be able to show that your podcast is truly focused on your commute route specifically, with actual content about locations along that route, and that you're consistently creating content during those drives. You also need real income from it. The IRS looks at whether there's a profit motive and if the activity is carried out in a businesslike manner. It's not a loophole if it's actually a legitimate business activity.

One other thing to consider is that you'll need to fill out a Schedule C for your podcast income, which means you'll pay self-employment tax on that income (about 15.3%). So make sure your deductions are actually saving you more than you're paying in SE tax if this is a small side hustle.

Thanks so much for sharing your similar experience! So just to be crystal clear - even though my parents are paying for a lot of my sister's expenses directly (they write checks to her landlord and utility companies), she can still claim her daughter for the CTC/ACTC as long as her daughter lives with her? But for HOH status, it matters whether my parents give the money to my sister first or pay the bills directly?

Yes, your sister can claim her daughter for CTC/ACTC regardless of who pays the bills, as long as her daughter lives with her for more than half the year and meets the other qualifying child tests. For Head of Household, it does matter who physically pays the household expenses. If your parents pay bills directly, those amounts don't count toward your sister "maintaining the home." She would need to pay more than half the total costs of keeping up the home using her own money (which could include money your parents give directly to her). If your parents are paying most bills directly, she might not qualify for HOH status, but she could still file as Single and claim her daughter for the child tax credits.

Not a dumb question at all! For 2023 taxes, the standard deduction for Single is $13,850 while Head of Household is $20,800 - that's almost $7,000 difference! Plus HOH has more favorable tax brackets. With your sister's income at $18,500, this could mean several hundred dollars more in her refund. The CTC/ACTC amounts are the same either way, but the HOH filing status itself is valuable.