Hmm that's a really good point. I did get a promotion in August that bumped me from about $52k to the $58k range, so that could definitely be affecting things. Do you know if there's a good way to calculate the prorated amounts when your income changes mid-year?

You'll need to separate your income and withholding into two periods: before and after the promotion. For each period, calculate the annual equivalent of that income level (what you would have made if you'd earned that same amount all year), figure the tax on that annual amount, then prorate it for the number of months at that rate. For example, if you made $4,333/month ($52k/12) for 7 months, then $4,833/month for 5 months, you'd calculate: (Annual tax on $52k × 7/12) + (Annual tax on $58k × 5/12) = Your actual tax liability. Then compare your actual withholdings to this amount.

The IRS2Go app is really more for checking refund status than doing calculations. I'd recommend using the official Tax Withholding Estimator on the IRS website or something like FreeTaxUSA which lets you run scenarios for free.

Yeah I used FreeTaxUSA last year for a move from Washington to Texas. It worked fine for me but both states don't have income tax so it was pretty simple. I think they do handle part-year state returns but not sure how good they are with the more complicated situations.

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!