Do you know if this applies to people who were living abroad in 2019-2020? I was an expat during that time and I know we sometimes get different deadlines, but I'm not sure how the COVID extensions affected that.

For expatriates, the standard rule is that you automatically get an additional 2 months (until June 15) to file. However, during 2020, the COVID extension superseded this since July 15 was later than the expat June 15 date. The three-year statute of limitations would still be calculated from the COVID-extended date (July 15, 2020), making your deadline July 15, 2023 - the same as domestic filers for the 2019 tax year. The only exception might be if you requested an additional extension beyond July 15, 2020, which would have pushed your original filing deadline to October 15, 2020. In that case, your statute of limitations would run three years from when you actually filed.

If you're owed a refund, unfortunately after July 15, 2023, you've missed the window to claim it for 2019. The three-year statute of limitations has expired. However, if you OWE taxes, the IRS still wants their money! You should file as soon as possible to minimize the penalties and interest that have been accumulating. The IRS can technically collect unpaid taxes for up to 10 years, so you're nowhere near that deadline. Filing now will stop additional failure-to-file penalties from growing.

Thanks for mentioning this! My AGI for 2023 will be around $175,000, so I'd need to hit the 110% threshold. My concern is that I've had very little withholding for 2024 since most of my income this year is from self-employment, and I didn't make any quarterly payments yet. That's why I was hoping to use the overpayment strategy to catch up a bit.

Based on your situation with $175,000 AGI and mostly self-employment income, you're right to be concerned about catching up on those estimated payments. The 110% safe harbor would definitely apply to you. Since you've missed the first couple of quarterly payments for 2024, you will likely face some underpayment penalties for those specific quarters. However, overpaying on your 2023 return will help minimize additional penalties going forward. Make sure to make your remaining quarterly payments for 2024 on time (September 15 and January 15) to avoid further penalties.

Does anyone know exactly how much the underpayment penalty actually is? Is it worth stressing about? I'm in a similar situation and wondering if I should just pay it and move on rather than jumping through hoops.

What constitutes a "formal agenda"? Like do I need to print something out, or is an email to the team sufficient? And do we need to do some kind of actual business discussion during the event?

An email to the team outlining the agenda and business purpose would be sufficient documentation, just make sure to save it. You don't need anything fancy - just something that shows this wasn't purely recreational. Yes, you should definitely include some business discussion or activities that relate to your company goals during the event. For example, if you're doing an escape room, you might frame it as team problem-solving training and have a brief session before or after discussing how those skills apply to workplace challenges. The key is creating a paper trail showing it was primarily for business purposes, not just fun.

That's a great point! I've been lumping all refreshments together in my accounting. So just to clarify - the coffee/snacks in our employee break room are 100% deductible, but the identical items put out for customers in our waiting area would be 50% deductible?

Do you literally need to make 4 equal payments? My income is super inconsistent - I might make $5k one month and $500 the next. How do you handle that with quarterly payments?

You don't need to make exactly equal payments. The IRS allows you to use the "annualized income installment method" which means you can make payments based on what you actually earned during each period. This is perfect for creators with inconsistent income. You file Form 2210 with your tax return to show that your uneven payments match your uneven income. Honestly though, I just try to hit at least 90% of my estimated tax liability for the year through my quarterly payments to avoid any penalties. The dates to remember are April 15, June 15, September 15, and January 15 of the following year.

There's a deduction for half of your self-employment tax though right? I remember reading something about that.

14 Did you end up having to pay those tickets? That sounds like a nightmare situation.

7 I contested the tickets by providing proof of the donation date and a copy of the signed title transfer, but it was a huge hassle that took nearly two months to resolve. The charity eventually took responsibility, but only after multiple angry phone calls. The DMV confirmed that filing the release of liability form would have protected me regardless of what the charity did or didn't do with the title. Lesson learned the hard way!

23 I researched them before donating. They are a legitimate 501(c)(3), but only about 40% of the proceeds actually go to their programs. The rest goes to advertising (those annoying jingles!) and administrative costs. I ended up donating to my local homeless shelter instead - they had a vehicle donation program where 85% of proceeds went directly to services.