Just wanted to add that there's a specific order of operations for claiming the self-employed health insurance deduction. It goes on line 16 of Schedule 1, not as a business expense on Schedule C. The amount can't exceed your husband's net earnings from self-employment. Also, if either of you were eligible for employer-sponsored coverage during any month, you can't claim the deduction for those months, even if you didn't enroll in that coverage.

I'm in a very similar situation - my wife retired last year and gets health insurance through her former employer's retiree plan, with premiums deducted after-tax from her pension. I was initially confused about whether I could claim these on my self-employment return. After researching this extensively and consulting with a tax professional, I can confirm what others have said: yes, you can deduct these premiums as long as they're paid after-tax and you file jointly. The key things to remember: 1. The deduction is limited to your husband's net self-employment income 2. You can't claim it for any months where either of you were eligible for subsidized employer coverage elsewhere 3. Keep good records showing the premiums were paid with after-tax dollars One practical tip: I set up a separate checking account that my business uses to reimburse my wife for her health insurance premiums each month. This creates a clear paper trail showing the business is paying for the coverage, which makes the deduction cleaner if you ever get audited. The fact that it's retiree coverage through your former employer doesn't disqualify it - what matters is that you're paying for it with after-tax money and your husband has the self-employment income to support the deduction.

One thing I haven't seen mentioned yet is the potential for estimated tax payments. With $115K in W2G winnings hitting your AGI, you might owe significant taxes that weren't withheld, which could trigger underpayment penalties if you don't handle it properly. Even though you have offsetting losses, the IRS calculates penalties based on your tax liability throughout the year, not just what you owe at filing. Your CPA should be able to help you determine if you need to make an estimated payment for Q1 2025 to avoid penalties, or if you qualify for any safe harbor provisions. Also, keep in mind that if your gambling was spread across multiple tax years (like if some of those W2Gs are from late 2024 transactions), you'll need to match your wins and losses to the correct tax year for each session. Online casinos sometimes issue W2Gs in January for December activity, which can complicate things. The documentation tools others mentioned like taxr.ai could be really helpful for organizing this by tax year and ensuring everything matches up correctly. Good luck with your CPA appointment!

I went through something very similar last year with about $85K in W2Gs but an overall net loss. A few key things that helped me navigate this mess: First, don't panic about the estimated payment penalties. There are safe harbor rules - if you paid at least 100% of last year's tax liability through withholding and estimated payments (110% if your prior year AGI was over $150K), you won't owe penalties regardless of what you owe this year. Since you mentioned usually getting refunds, you might already be covered. Second, definitely get those casino statements ASAP. I found that FanDuel and BetMGM were pretty good about providing detailed win/loss statements, but it took a few weeks to get them. Don't just rely on your downloaded transaction history - the official statements carry more weight. Third, regarding your benefits concerns - yes, the increased AGI will likely affect your healthcare subsidies and your son's FAFSA. However, there might be some flexibility depending on when you file and when those determinations are made. Your CPA might suggest strategies around timing or amended returns if needed. The session method documentation is crucial, but make sure your CPA is experienced with gambling taxes. Not all CPAs are comfortable with this area, and you want someone who knows the ins and outs of AM-2008-011. It made a huge difference having someone who understood the nuances rather than someone just winging it. Hang in there - it's stressful but definitely manageable with proper documentation and the right professional help!

Does your parenting plan specifically state who claims which child each year? Or does it just say you "split" them? This could make a difference.

I understand your frustration completely. The disconnect between family court orders and actual IRS rules creates these impossible situations for parents. Based on what you've described, you likely had your son for significantly more than 183 nights this year (the IRS threshold for custodial parent status), especially with that 4-month absence. Under IRS rules, the custodial parent has the primary right to claim the child as a dependent. However, you're caught between two systems: the IRS rules that would likely support your claim, and a court order that could hold you in contempt if violated. My suggestion would be to document everything - every night each child stayed with you versus your ex, all expenses you covered during the absence period, any communication about the missed parenting time. Then consider going back to court specifically requesting a one-year modification to the tax arrangement based on the actual custody time this year, not a permanent change to the parenting plan. You might also want to speak directly with an IRS agent about your specific situation. They can clarify whether your actual custody time this year would qualify you as the custodial parent under their rules, which could strengthen your position if you need to return to family court.

Just to clarify something that hasn't been mentioned yet - the routing number for Cash App is actually the routing number for Sutton Bank or Lincoln Savings Bank (depending on when you opened your account). I remember back in 2022 when I first used Cash App for taxes, I was confused about this. Make sure you're using the routing and account numbers shown specifically in the Cash App direct deposit section, not just your Cash App $cashtag. The IRS doesn't recognize $cashtags, only proper bank routing and account numbers.

I've been using Cash App for tax refunds for the past three years and wanted to share my experience. My DDDs were typically in late February, and I consistently received my refunds 1-2 days early each time. What I really appreciate is the instant notification when the deposit hits - no more obsessively checking my account balance! One tip I'd add to what others have mentioned: make sure your Cash App account is fully verified before tax season. I learned this the hard way my first year when there was a brief delay because my identity verification wasn't complete. Also, keep screenshots of your routing and account numbers from the app when you file, just in case you need them for reference later. Overall, I've had a very positive experience and would recommend it, especially if you like getting your money a bit earlier than expected!

I've been a domestic missionary for 7 years now and I handle my taxes by setting up as a sole proprietor with a Schedule C. I track all income from churches as "Professional Services" and keep careful records of my ministry-related expenses. One thing thats often confusing is when churches give "love offerings" vs regular support. My CPA says that if theres an expectation of service (like regular monthly support) its taxable self-employment income, but true "gifts" with no expectation of service might not be taxable.

One important aspect that hasn't been fully covered is quarterly estimated tax payments. As a missionary receiving support from multiple sources, you'll likely need to make quarterly estimated tax payments to avoid underpayment penalties, especially since churches typically don't withhold taxes from their support payments. The IRS generally requires you to pay at least 90% of the current year's tax liability or 100% of last year's (110% if your prior year AGI was over $150,000) through withholding and estimated payments. Since missionary income can be irregular, I recommend setting aside 25-30% of each support payment for taxes and making quarterly payments using Form 1040ES. Also, don't forget about the potential for state tax implications. Some states have different rules for religious workers, and if you're traveling between states for ministry work, you might have multi-state tax filing requirements depending on where your supporting churches are located and where you perform your ministry activities. It's worth consulting with a tax professional who has experience with missionary taxation, as the intersection of self-employment rules, religious worker provisions, and multiple income sources can get quite complex.