That's actually a really good point that I hadn't considered! My income is definitely below the Roth limits (about $95k for 2023), but maybe my advisor was assuming I'd be doing a backdoor Roth? I'll ask them specifically if that's what they were suggesting. If they were just mistaken about regular Roth contributions needing Form 8606, it might be time to find a new advisor...

Definitely worth a clarifying conversation with them. If your income is $95k, you're well within the limits for direct Roth contributions ($138,000 for single filers in 2023), so backdoor wouldn't be necessary. Some tax advisors who deal primarily with higher-income clients get so used to recommending backdoor Roth strategies that they sometimes default to that advice without checking if a direct contribution is possible. Or they might just be confusing the reporting requirements between traditional and Roth IRAs.

This happened to me too! Fidelity assumed my April contribution was for the current year not the previous year. Took forever to get fixed and they had to generate corrected tax forms.

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!

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.

That's a great point! He definitely had some expenses - mostly software subscriptions and a new laptop he had to buy specifically for this job. I wasn't sure if we could deduct the full cost of the laptop or if we needed to depreciate it.

For the laptop, it depends on when he purchased it and how much it cost. If it was under $2,500, you can potentially use Section 179 to deduct the full cost in one year, assuming it was used more than 50% for business. For the software subscriptions, those are generally fully deductible as business expenses in the year paid. Just make sure you keep receipts for everything. You might also want to look into home office deduction if he was working from home - you can either use the simplified method ($5 per square foot up to 300 square feet) or the regular method which calculates the actual expenses.

Is there any way to reduce the self-employment tax hit? That 15.3% is brutal when you're already paying regular income tax too.

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.