Is that seriously true that both spouses have to choose the same deduction method?? I had no idea! We were planning to have my husband itemize since he has tons of deductible expenses while I'd take the standard deduction. Will this really not work?

Yes, it's absolutely true and it's one of the biggest "gotchas" with married filing separately. If one spouse itemizes, the other MUST also itemize - even if they have very few deductions. This often means the second spouse ends up with a very small itemized deduction amount that would have been much better served by taking the standard deduction. This requirement often wipes out much of the potential benefit of filing separately, which is why it's so important to run the numbers both ways. The tax code deliberately makes MFS less advantageous in most situations to encourage joint filing.

I've had similar experiences with TurboTax too. These programs often show "refund estimates" before they've calculated everything. Sometimes they don't include state taxes or certain penalties until the very end of the process.

Do you need any special documentation for mileage deductions? I'm worried about getting audited.

You should keep a log with the date, starting/ending mileage, destination, and business purpose. Most mileage tracking apps record this automatically. You don't have to submit this with your taxes, but you need to have it if you get audited. I personally use an app that automatically tracks when I'm driving and lets me categorize trips as business or personal. It generates reports I can give to my accountant or use if I ever get questioned by the IRS. The key is being consistent and only claiming legitimate business miles.

That's a really good point. I got hit with back sales taxes when my state found out about my Etsy shop. Do services like bathroom remodels have sales tax though? I thought it was just for products?

Just checked my pay stub and it does say "Single" for filing status, but there's nothing about multiple jobs. I do max out my 401k ($22,500/year) and have an HSA that I put about $3,000 into annually. Could those really affect my withholding that much? I thought those were smart financial moves.

Those are absolutely smart financial moves! The issue isn't that you're doing anything wrong - it's that the withholding system doesn't always account for them perfectly. When you contribute to 401k and HSA, your taxable income for each paycheck is lower, so the system withholds less tax. However, those contributions don't reduce your tax brackets - they just reduce your total taxable income. If you're near a bracket threshold, this can create a withholding gap. This explains the difference between you and your coworkers too. If they're not maxing retirement accounts, their withholding calculation is more straightforward. Your situation is actually financially better (huge retirement savings), but it requires manual adjustment to your withholding to avoid the surprise tax bill.

The IRS calculator isn't technically broken, but it's not great for complex situations. It works best for people with one job, standard income, and no special circumstances. The moment you add variables like education expenses, multiple income sources, or significant pre-tax deductions, it falls apart. I found the calculator on smartasset.com to be much more accurate for estimating actual withholding needs. It lets you input more details about your specific situation.

Thanks, I'll check out that other calculator. I was starting to think I was going crazy because I followed the IRS calculator recommendations exactly and still ended up owing over $2k. Good to know it's not just me!

That's actually a really smart idea I hadn't considered. I could probably scrape together about $3,000 by the deadline. Would I just make a partial payment through the IRS website and then pay the remainder later? Or do I need to indicate somewhere that it's a partial payment?

Just make the payment through the IRS Direct Pay or another official payment method for whatever amount you can afford. There's no need to mark it as "partial" - the IRS system automatically matches your payments to your tax liability and will show any remaining balance due. Then when you get the rest of the money, make another payment for the remaining balance. The penalties and interest will only apply to the unpaid portion. Both payments would be made exactly the same way - there's no special process for making multiple payments.

For a 4-day late payment of $5,650, the math works out to: Failure-to-pay penalty: 0.5% per month, prorated for 4 days = about 0.067% × $5,650 = $3.78 Interest: Currently about 7% annually, prorated for 4 days = about 0.077% × $5,650 = $4.35 So total damage would be roughly $8.13 if paid exactly 4 days late.

This is exactly right. Business losses from scams are still deductible as business expenses if they occurred in the normal course of business. It's only personal theft losses that got eliminated (except for federally declared disasters). OP, was this investment somehow connected to any business activities or was it purely personal? That makes a huge difference in deductibility.

You can also try contacting CFPB (Consumer Financial Protection Bureau) if a bank or financial institution was involved in any way with the transactions. They sometimes can put pressure on financial institutions that may have facilitated the scam.

Thanks for the suggestion! I did file a report with IC3 already but haven't heard anything back yet. It's been about 3 months since I filed the report. I'll check out the CFPB option too. My bank wasn't much help since I authorized the transfers myself (stupid, I know), but maybe CFPB could still do something.