That's a smart idea. Do you know if there's any way to make an extra payment to the IRS before I file to make up for the shortage?

Yes, you can make what's called an "estimated tax payment" to the IRS before you file. Go to IRS.gov and search for Form 1040-ES, or you can pay directly through their online payment system. Just make sure you keep the confirmation for when you file your taxes so you can properly credit that payment. If your employer fixes the issue and reimburses you later, that payment you made won't go to waste - it'll either reduce what you owe next year or increase your refund when you file for 2025.

This is good advice about the additional withholding. You can also ask them to take out a specific extra amount from each check for the rest of the year to make up for the underwithholding earlier.

That makes a lot of sense actually. She always refused to adjust her W-4 forms when I suggested it. Is there any way to prove this was the cause of our big tax bill rather than my withholding being insufficient?

You can definitely prove this by having a tax professional create a withholding analysis. They would look at both of your W-2 forms, which show exactly how much was withheld from each paycheck throughout the year. The analysis would compare the actual withholding to what should have been withheld based on your total income and tax brackets. This will clearly show if her dual employment without proper withholding adjustment was the primary cause of the shortage. Most tax pros can prepare this kind of analysis in about an hour, and the documentation would be very useful for your divorce settlement negotiations.

Innocent spouse relief probably won't apply in this situation. That's typically for cases where one spouse did something fraudulent or didn't report income without the other spouse's knowledge. In this case, it sounds like everything was reported correctly, they just owe a lot. The IRS does offer something called "separation of liability relief" though, which might be helpful after the divorce is finalized. But you usually need to wait until after the divorce is done to apply for that.

This is super helpful! My program coordinator mentioned something about the practical hours counting toward credits but I didn't connect that to the tax implications. Does that mean I should include all my apprenticeship hours and not just the classroom time when figuring out if I meet half-time status?

Yes, absolutely include all hours that the college is counting toward your credits or certificate. Many apprenticeship programs are structured so that your on-the-job training hours translate to a certain number of credits in addition to your classroom time. For example, I had a client whose 4-week classroom portion only equated to 4 credits, which wouldn't meet the half-time requirement. But when we included the supervised work experience that was part of the program curriculum (which added another 4 credits), they qualified for AOC. The key is that these work hours must be formally recognized by the educational institution as part of your academic program.

Yes, online courses absolutely count toward your workload calculation for AOC purposes as long as they're part of your eligible program and offered by a qualifying educational institution. The IRS doesn't distinguish between delivery methods (online vs. in-person) when determining eligibility. What matters is the credit hours or equivalent as determined by your educational institution. For your situation with 3 weeks in-person plus 4 weeks online, you'd need to find out how many total credits/units that represents at your institution and whether it meets their half-time threshold.

That's a good point. Do you think a tax attorney would be better than a CPA for my situation? I'm worried about the additional cost since I'm already struggling with the tax debt itself.

For your specific situation with stock sales and cascading tax consequences, I'd recommend a tax attorney over a CPA. While CPAs are excellent for tax preparation and general advice, attorneys have specialized knowledge of tax relief programs and negotiation with the IRS that's particularly relevant to your case. They can also represent you in Tax Court if it ever comes to that. Regarding cost concerns, many tax attorneys will work on a flat fee basis for tax resolution cases rather than hourly billing. During a free consultation, ask about their fee structure and whether they can give you a fixed quote. Often the money saved through proper representation exceeds the cost of hiring them, especially with tax debts in the six-figure range you're facing.

I actually went through this process! Innocent spouse relief is legitimate but pretty specific in when it applies. You need to show that you didn't know and had no reason to know about the underreported income or incorrect deductions when you signed the return. If you were aware of the stock sales but just didn't understand the tax implications, that typically doesn't qualify.

This is helpful but you missed Code C which is for taxable cost of group-term life insurance over $50,000. That's the one I always get confused about because I have to pay taxes on that benefit even though I never saw the money!

You're absolutely right about Code C! That's an important one I should have included. For group-term life insurance over $50,000 provided by your employer, the cost of coverage over $50,000 is considered taxable income. The confusing part is that this amount is already included in your Box 1 wages, so you don't need to add it again when filing. It's basically showing you what portion of your taxable wages came from this benefit that you never actually received as cash.

What tax software did you use? I have 3 W-2s this year (worked multiple jobs) and I'm worried about messing something up with all these codes.