Wouldn't amending returns from potentially years ago be super complicated though? And aren't there time limits on how far back you can amend?

You're right that there are time limits - generally 3 years from the original filing date or 2 years from when you paid the tax, whichever is later. So this approach only works if the inventory was purchased relatively recently. The complexity really depends on your specific situation. If most of the stolen inventory was purchased in the last couple of years, amending might actually be cleaner than trying to figure out the theft loss calculations. But if the inventory was accumulated over many years, then the theft loss approach on Form 4684 probably makes more sense despite the complications.

The IRS Disaster Resource Center is specifically for federally declared disasters, so it wouldn't apply directly to a robbery situation. However, you're right that some of their calculation methods could be helpful as a reference. For a robbery, you'd be better off looking at the specific IRS guidelines for theft losses in Publication 547. There's also some good information in Publication 584-B (Business Casualty, Disaster, and Theft Loss Workbook) that has worksheets for calculating and documenting business losses.

Does a Currently Not Collectible status affect the 10-year period? I got placed in CNC status for a couple years when I was unemployed, and I'm wondering if that changed my CSED.

Currently Not Collectible (CNC) status does NOT extend the 10-year statute of limitations. This is actually one of the better options if you're trying to reach the end of the collection period, because the IRS stops active collection efforts while the 10-year clock continues to run. The main advantage of CNC is that unlike an installment agreement or Offer in Compromise, requesting CNC status doesn't extend the CSED. Many people don't realize this and end up requesting payment plans that add time to their collection period when CNC might have been a better option.

Actually, that's not entirely correct. The 10-year period is extended while the IRS is considering your installment agreement request, plus an additional 30 days - not just when you file the form. Also, there are very specific rules about when extensions happen with OICs and appeals. It's more nuanced than just calling and asking.

Thank you for the specific calculation - that's really helpful! So if I'm understanding correctly, the issue is two-fold: my regular paychecks have too little withheld AND my bonuses should have 22% federal tax taken out but have zero instead? Would requesting the additional withholding on regular paychecks be enough to cover both problems?

Yes, your understanding is correct - you have two separate withholding problems happening simultaneously. Your regular paycheck withholding is likely calculated based only on your base salary, not accounting for the additional income from bonuses. And then your bonuses should have 22% federal withholding but have zero. The additional withholding I calculated would only cover the missing withholding from your bonuses going forward. You'll also need to address the underwithholding on your regular paychecks. I'd recommend talking to your payroll department first to get the bonus withholding fixed, then use the W-4 additional withholding to cover any remaining gap. You may also need to save some money to cover what's already been underwitheld so far this year.

This happened at my company too! When I brought it up to HR they got super defensive. I ended up comparing paystubs with colleagues and found out they were underwithholding for everyone. The company eventually had to send out an email explaining the "payroll configuration adjustment" but never admitted fault.

I never thought about it being deliberately misconfigured... that's concerning. I'll definitely ask around to see if my coworkers are experiencing the same thing. The company has been growing really fast so it could be an oversight, but either way I need to get it fixed. I appreciate everyone's advice - I'll update after talking to HR!

I've used Form 4852 twice when employers either sent incorrect W2s or I couldn't obtain them. Both times went smoothly - the IRS did not audit or question the returns. Just make sure your estimates are reasonable and as close as possible to the actual amounts. Using your final pay stub is the best approach since the YTD figures should be very close to the W2 amounts.

That's interesting! I've actually been thinking about doing some financial consulting on the side. How much of a side business do you need to have for this to be legitimate? And do you need to form an actual LLC, or could you just report the income on a Schedule C?

You don't necessarily need a formal LLC - that's just what I chose for liability protection. You can absolutely report side business income and expenses on Schedule C as a sole proprietor without forming any legal entity. As for how much business you need, there's no specific threshold, but the IRS does look for a profit motive. Generally, if you show a profit in 3 out of 5 years, they consider it a legitimate business rather than a hobby. Start tracking all business mileage from day one with a good app or logbook, noting the date, starting/ending mileage, purpose, and client. Just make sure you're only deducting the portion used specifically for your side business, not your main employment.

For leases, you can actually use either method (standard mileage or actual expenses), but there's a catch: if you choose standard mileage in the first year, you can switch between methods in later years. But if you use actual expenses in the first year, you're stuck with that method for the duration of the lease. Most people find the standard mileage rate (65.5 cents per mile for 2023) simpler since you just track miles rather than every expense. But actual expenses might be better for luxury vehicles or in high-cost areas. Do a calculation both ways for your first year to see which gives you the bigger deduction.