This isn't just unemployment fraud, it's also tax fraud. When filing your taxes next year, the timing of your unemployment benefits will align perfectly with your new dependent. IRS systems are designed to catch inconsistencies like this. I worked in payroll for 10 years and saw an employee attempt something similar. They ended up having to repay all unemployment benefits plus a 30% penalty, and their employer faced significant fines for encouraging the fraud. If your employer wants to help you, there are legitimate options like offering a paid leave policy, allowing remote work, or setting up a temporary part-time arrangement. If they truly value you, they should be willing to find a legal solution rather than putting you at risk.

As someone who processes unemployment claims, I can tell you we ABSOLUTELY look for this pattern and it's an automatic flag in our system. When someone files for unemployment then returns to the same employer shortly after having a baby, it triggers a mandatory review. Your employer is asking you to commit a federal offense that could result in: - Repaying all benefits with penalties - Being barred from receiving legitimate unemployment in the future - Potential criminal charges in severe cases - Tax complications with the IRS Plus, your employer could face significant fines for instructing you to commit fraud. If they're willing to do this, I'd be concerned about what other corners they're cutting that might affect you.

For the 1099-NEC specifically, I file one every year for my side gig. It's really not as scary as it seems! Schedule C is basically just telling the IRS "here's what I made and here's what I spent to make it." Even if you have zero expenses, you still file it but just put $0 for all the expense categories. One thing to note: you said you don't need Schedule SE because it's under $400, which is mostly right, but you still need to include the self-employment income on your total income for the year. That flows through from your Schedule C to Schedule 1 and then to your 1040. For tax software, many have free options that include Schedule C now! Try the IRS Free File options before paying for TurboTax.

Just a heads up for the scholarship reporting - I was in the exact same situation last year and most tax software actually has a dedicated section for entering scholarship income. When you enter your 1098-T, it'll ask about the amounts and whether they were used for qualified education expenses. The software then automatically handles the "SCH" notation so you don't have to worry about the "to the left" instructions. For the 1099-NEC tutoring income, I also had a small amount last year from a teaching assistant position. The Schedule C looks intimidating but it's actually super simple for straightforward situations like tutoring. You'll just enter the income, any expenses (even if zero), and the software calculates the rest.

Don't forget to check if your husband's company provided a Form 3922 for the ESPP purchases. This form provides the information needed to calculate your basis and holding periods. For the matched shares, some companies treat them as RSUs rather than part of the ESPP program, which might explain why they're handled differently. In my experience, the key is determining if tax was already withheld when the matched shares were granted. Check his paystubs from around the grant dates - sometimes the income and withholding for stock compensation appears there but is aggregated differently on the W-2.

One thing nobody has mentioned yet - check if your husband's company offers a "Section 83(b) election" for the matched shares. This would allow you to pay tax on the shares at the grant date (based on FMV then) rather than at vesting, which could be advantageous if the shares are expected to appreciate significantly. The deadline for this election is 30 days after receiving the shares though, so it may be too late if he's already had them for a while. Just something to keep in mind for future grants!

Something nobody's mentioned yet - if your partner gets any per diem or allowance from the union for these travel expenses, that changes things. My union provides a travel stipend for jobs beyond a certain distance, and that needs to be reported differently on taxes. If they're getting any kind of travel allowance or per diem that isn't included on their W-2, that needs to be handled carefully. Also worth checking if your partner's collective bargaining agreement has any provisions about travel reimbursement they might not be taking advantage of.

I'm an electrician with similar situation. One important thing - if your partner gets a W-2 (rather than 1099), these deductions got much harder after the 2018 tax law changes. Employee business expenses used to be deductible on Schedule A, but now they're basically eliminated for W-2 workers until 2025 when the law changes again. If they're truly an employee (W-2), they might be out of luck unless their employer is willing to set up an accountable plan to reimburse these expenses tax-free. If they're considered self-employed (getting 1099-NEC), then they can deduct these business expenses on Schedule C.

I think the Forbes article might have been technically correct but just explained it poorly. The 15.3% is Social Security (12.4%) + Medicare (2.9%). The Social Security part only applies up to the wage base (which changes yearly). The Medicare 2.9% applies to all SE income. The ADDITIONAL 0.9% Medicare tax (which brings it to 3.8% total) kicks in at higher income levels ($200k/$250k). The article maybe just didn't mention this additional tax? Either way, I agree that tax info is confusing. I always double check the IRS website and cross-reference with Publication 15 and Publication 334.

Has anyone else noticed that the wage base for Social Security taxes increases every year? In 2023 it was $160,200, up from $147,000 in 2022. For 2025 it's expected to be around $168,600. This is why old articles can be misleading - tax numbers change annually but articles rarely get updated!