You might also want to check if you need to make an estimated tax payment this quarter rather than waiting until tax time. If you're normally a W-2 employee who gets refunds, you're probably fine waiting. But if this pushes your tax due over $1k for the year beyond what's being withheld, you might need to make an estimated payment to avoid an underpayment penalty.

Congratulations on your win! You've gotten some great advice here already. Just to add a bit more clarity - yes, you absolutely need to report this as "Other Income" on your tax return regardless of whether you receive a W-2G form or not. One thing I'd suggest is opening a separate savings account and immediately putting aside 25-30% of your winnings ($1,200-$1,440) for taxes. This covers both federal and state obligations and gives you a small buffer. It's much easier to do this now while you have the full amount than to scramble for tax money next April. Also, start keeping a simple log of any gambling activities for the rest of the year - both wins and losses. Even if you just buy a few lottery tickets or play bingo, track it all. If you itemize deductions, those losses can offset your winnings dollar-for-dollar up to the amount you won. The IRS considers all gambling winnings taxable income from dollar one, so there's no minimum threshold for reporting requirements on your end, even though there are thresholds for when organizations must issue forms to you.

Just went through this exact situation last year! The shock to the paycheck is real - we weren't prepared for how much the taxes would increase beyond just the premium amount. One thing that really helped us was requesting a "benefits statement" from HR that breaks down both the employee and employer portions of the insurance costs. This gave us the exact dollar amount being added as imputed income, which made calculating the tax impact much clearer. Also, if your partner's company offers a cafeteria plan or FSA, you might be able to use pre-tax dollars for some medical expenses to offset some of the tax burden. It won't help with the imputed income piece, but every bit helps when you're dealing with the double taxation on domestic partner benefits. The silver lining is that this will all be much clearer when you get the W-2 next year - you'll see exactly how much was added as imputed income in Box 1 (wages) versus what would have been there without the domestic partner coverage.

Just wanted to add another perspective on tracking these costs - I found it helpful to create a simple spreadsheet comparing my partner's paychecks before and after adding domestic partner coverage. What really opened my eyes was looking at three key numbers: 1) The obvious premium deduction ($230 in your case), 2) The imputed income amount (which should show up somewhere on the paystub, even if it's coded weirdly), and 3) The actual tax increase on both the premium AND the imputed income. One thing I wish someone had told me upfront - the "catch-up" payments you mentioned for the first two months might also affect how much extra tax gets withheld. Your partner's payroll system might be calculating withholding as if she's going to earn that higher amount every paycheck for the full year, which could result in over-withholding that you'd get back as a refund. If the tax hit is really severe, you might also want to look into whether her company offers any domestic partner benefits that could help offset some of the cost, like dependent care assistance or commuter benefits. Every little bit helps when you're dealing with the federal tax penalty for not being legally married!

Check your state laws too! Some states have additional protections for employee reimbursements. In California, for example, Labor Code Section 2802 requires employers to reimburse employees for all necessary expenses incurred while performing their job duties. Your state might have something similar.

This is a frustrating but unfortunately common issue in the delivery industry. Your employer is definitely making a mistake that's costing everyone money. When mileage reimbursements are handled correctly under an "accountable plan," they should be completely tax-free for both you and your employer. The key requirements for an accountable plan are: 1) the reimbursement must be for legitimate business expenses, 2) employees must substantiate the expenses (like tracking miles), and 3) any excess reimbursements must be returned. Since you're getting paid below the federal mileage rate and presumably tracking your deliveries, this should easily qualify. I'd suggest documenting everything - your actual mileage, the reimbursement rate you're receiving, and how it's being reported on your paystubs. Then approach your employer with IRS Publication 463 which clearly explains how mileage reimbursements should work. Emphasize that fixing this will save THEM money too on payroll taxes. If that doesn't work, you might need to file amended tax returns for previous years to recover overpaid taxes, though that's more complicated. The main thing is getting it fixed going forward so you're not artificially inflating your taxable income with money that's just covering your car expenses.

One important thing no one has mentioned: if you go to a TAC office, you MUST call ahead for an appointment specifically for ITIN services. You can't just walk in for this service. Also, if your spouse entered the US on any kind of visa that allowed work (even if she's not working), she might actually qualify for an SSN instead of an ITIN. Worth checking that angle first since an SSN is way more useful long-term.

I went through this exact situation with my husband from Germany two years ago, and I completely understand your stress about the passport! Here's what we learned: The key is definitely using a Taxpayer Assistance Center (TAC) appointment. You can get an ITIN without any US income - we did it specifically for future joint filing benefits even though my husband wasn't working yet. A few practical tips from our experience: - Book your TAC appointment as early as possible (we had to wait 3 weeks in our area) - Bring your completed tax return, the W-7 form, passport, marriage certificate, and maybe a utility bill showing both names - The appointment took about 45 minutes total, and they made certified copies of everything right there - We got the ITIN about 6-7 weeks later One thing that really helped us was calling the IRS beforehand to confirm exactly what we needed to bring. The agent was super helpful and walked us through the process step by step. Don't stress too much - thousands of people go through this process successfully every year. The TAC route is definitely the safest way to handle original documents, and the agents there are experienced with ITIN applications for spouses.

Ugh, I made a HUGE mistake with this last year. I got a 1099-K from PayPal for about $8,500 in sports betting deposits and freaked out, so I just reported it all as "Other Income" without deducting my losses. Basically paid taxes on money that was just moving between accounts. Anyone know if I can still file an amended return for 2024? And what forms I would need to do that?

This is exactly why proper record-keeping is so crucial for online gambling! I went through a similar situation with BetRivers and Cash App transactions last year. The key thing to remember is that the 1099-K threshold dropped to $600 in 2022, so a lot more people are getting these forms now who never received them before. This is causing massive confusion because people think they owe taxes on the full amount shown. One thing I'd add to the great advice already given - if you're planning to continue sports betting, consider opening a dedicated bank account just for gambling transactions. This makes it much easier to track deposits, withdrawals, and actual net gains/losses for tax purposes. It also helps separate your gambling activity from your regular finances, which can be helpful if the IRS ever has questions. Also, don't panic about the 1099-K! The IRS is aware that these forms often show transaction volume rather than taxable income, especially for gambling and online sales. As long as you report your actual gambling winnings correctly and keep good documentation, you'll be fine.