One thing I learned the hard way - if most of your income is from a regular job with withholding, you can also just increase your withholding for the rest of the year instead of making separate estimated payments. Just update your W-4 with your employer to take out extra money from your remaining paychecks. The IRS treats withholding as if it occurred evenly throughout the year, even if you increase it late in the year. This can sometimes help avoid the penalties for quarterly underpayment since estimated payments are tied to specific quarters.

As someone who's been through this exact situation, I'd recommend acting quickly since we're getting close to the end of the year. With your $68k capital gain on top of your $135k salary, you're definitely in territory where estimated payments make sense. Here's what I'd suggest as your immediate action plan: 1. Calculate 110% of last year's federal tax (since your AGI will be over $150k this year) 2. Check how much has already been withheld from your paychecks this year 3. Pay the difference as an estimated payment for Q4 The good news is that even though you realized the gains recently, making one payment now for the current quarter should protect you from penalties as long as you meet the safe harbor rules. Also, don't forget to check if your state has similar estimated payment requirements - many do, and the penalties can add up if you miss those too. You can make the federal payment directly through the IRS website using their Direct Pay system. Just make sure to specify it's for the current tax year and the correct quarter.

Can someone explain how the 0%/15%/20% brackets work for qualified dividends? Is it the same income thresholds as regular tax brackets? I'm confused about when the rate jumps from 0% to 15%.

This is such a great question and one that trips up a lot of people! The key thing to remember is that ALL your income sources (wages, ordinary dividends, qualified dividends, interest, etc.) get added together to determine your total taxable income after deductions. That total taxable income number is what determines which tax bracket you fall into for BOTH your regular income tax rates AND your qualified dividend rates. So yes, if you have a bunch of ordinary dividends, they absolutely can push your qualified dividends into a higher tax bracket. Here's a simple example: Let's say you're single and after deductions your taxable income would be $40,000 from just wages. Your qualified dividends would be taxed at 0%. But if you also have $10,000 in ordinary dividends, now your total taxable income is $50,000, which pushes your qualified dividends into the 15% bracket. It's worth doing some planning around this, especially near year-end, to see if you can manage your income to stay in a lower qualified dividend bracket if possible!

Something no one has mentioned yet about QBI - there are income thresholds where the calculation gets MUCH more complicated. For 2025, if your taxable income exceeds $191,550 (single) or $383,100 (married filing jointly), the QBI deduction starts to phase out for certain businesses. If your business is a "specified service trade or business" (like health, law, accounting, consulting, financial services, etc.), you could lose some or all of your QBI deduction when you hit those thresholds. For other businesses, the calculation becomes based on W-2 wages paid and property owned. Since you're building a spreadsheet, you might want to include a "warning flag" if your income approaches these thresholds so you know when you need to consult a tax professional!

Great discussion here! As someone who struggled with these exact calculations when I started freelancing, I wanted to add a few practical tips for your spreadsheet: 1. **Create separate cells for each step** - don't try to do everything in one formula. Break it down like: - Cell A: Gross Revenue ($135,000) - Cell B: Business Expenses ($25,000) - Cell C: Net Earnings (A-B = $110,000) - Cell D: SE Tax (C * 0.9235 * 0.153 = $15,543) - Cell E: Half SE Tax (D/2 = $7,771.50) - Cell F: QBI (C - E = $102,228.50) - Cell G: QBI Deduction (F * 0.20 = $20,445.70) 2. **Add validation checks** - I include formulas that flag potential errors, like if my QBI calculation seems off compared to net earnings. 3. **Build in the income thresholds** that Jamal mentioned - have your spreadsheet automatically warn you if you're approaching the phase-out limits for QBI. The key insight that took me forever to understand: retirement contributions reduce your *taxable income* but not your *QBI*. They're calculated independently and both subtracted from your income. Once I got that straight, everything else fell into place!

Listen, the IRS site is notoriously glitchy on mobile. Been that way for yrs. Most ppl don't realize their system runs on ancient tech that barely works w/ modern browsers. Quick fixes that work for most: - Try incognito/private browsing mode - Desktop comp > phone ALWAYS - Clear cookies/cache before trying - Try diff browser (Firefox tends to work better) - Log in super early AM or late PM If none of that works, just call the transcript req line (800-908-9946). Takes 5-10 days but way less hassle than fighting w/ their garbage website. Trust me, I've been down this rabbit hole many times.

I've been dealing with this same frustrating issue! What worked for me was switching to a different network entirely - I was on my home WiFi when having problems, but when I tried using my phone's cellular data instead, it worked perfectly. Sometimes the issue isn't just the browser or device, but the network connection itself. The IRS authentication system can be really finicky about certain internet providers or network configurations. If you have access to a different WiFi network (maybe at a library, coffee shop, or friend's house), give that a try. Also, make sure your phone's date and time are set correctly - I know it sounds weird, but security certificates can fail if your device clock is off by more than a few minutes. This happened to me with a different government site last month. Hope this helps! The transcript system really shouldn't be this difficult to use in 2025.

Something everyone's missing - check if you even needed to file! If your income is only 4100 Swiss francs annually (roughly $4500 USD), that's below the filing threshold for most years. For 2022, the standard deduction was $12,950 for single filers, so if you earned less than that, you weren't even required to file a US return. For your retired mom, it depends on her income sources and amounts, but the thresholds are different for seniors. Don't waste money on expensive tax specialists until you determine if you even had a filing requirement based on your income level!

Just wanted to add some reassurance from someone who went through this exact situation! I'm a dual citizen (US/German) who hadn't filed US taxes in 8 years while living in Berlin. I was absolutely terrified about traveling to the US for my sister's wedding. Like everyone else has said, there's zero connection between IRS tax compliance and border control. I've traveled to the US multiple times while getting my tax situation sorted out, and it was never an issue. The border agents only care about your passport validity and standard security screening. I used the Streamlined Foreign Offshore Procedures to catch up on my filings. With your income level and the Foreign Earned Income Exclusion, you'll likely owe nothing. The process took about 6 weeks total, but I didn't wait to travel - I started the process after my trip. Your dad should be fine too. Retired expats are actually in a better position since pension income often has favorable tax treaty treatment. Just enjoy your Boston trip and deal with the tax compliance when you return. The anxiety is so much worse than the actual reality!