Quick question - how would this even show up on a paystub? Would it be obvious if an employer was making you pay both halves of FICA? My paystubs are confusing and just show a bunch of different deductions.

I went through something similar at my previous job and want to share what I learned. Your employer's request is definitely illegal, but I'd also recommend checking if they've already started doing this without telling you properly. Look at your most recent paystub and calculate what your FICA withholding should be: multiply your gross pay by 0.0765 (that's 7.65% total for employee portion). If the actual withholding is close to double that amount (around 15.3%), they may have already started making you pay both portions. Also, keep in mind that if your employer does this, you'll essentially be overpaying your taxes. When you file your tax return, you should get a refund for the overpaid amount, but that doesn't make what your employer is doing legal. You shouldn't have to wait until tax season to get back money that was illegally withheld from your paychecks. Document everything - the conversation with your boss, your current and future paystubs, and any written communication about this policy. This documentation will be crucial whether you decide to confront your employer or report them to the IRS.

I've been using UltraTax CS for my family trust returns for the past 3 years and it's been solid. It's definitely more expensive than consumer software (around $500-600 annually), but the reliability has been worth it after dealing with similar issues you described with H&R Block. What I really appreciate is how it handles the flow-through calculations from the 1041 to the K-1s automatically, and it has excellent error checking that catches common trust return mistakes before you file. The interface takes some getting used to if you're coming from consumer software, but their support team actually knows trust taxation rules, which has been helpful when I've had questions about distribution deduction calculations. One thing to note - they require you to maintain the subscription annually even if you only file during tax season, so factor that into your cost comparison. But given your bad experience with H&R Block's reliability issues, it might be worth the peace of mind to use something designed for professional preparers.

I went through a similar software nightmare with trust returns a few years ago and ended up switching to ProSeries. It's been rock solid for Form 1041 preparation and handles all the K-1 complexities without any of the freezing issues you experienced with H&R Block. What really sold me on ProSeries was how it handles the trust-specific calculations automatically - things like the distribution deduction, DNI calculations, and the proper allocation of different income types to beneficiaries. The software walks you through each step and has built-in checks to catch common trust return errors before filing. The price is reasonable (around $400-450 annually) and includes unlimited e-filing, so both your trusts would be covered. Their customer support actually understands trust taxation, which was a huge relief after dealing with consumer software support that clearly had no clue about fiduciary returns. One feature I particularly love is that it saves your work automatically every few minutes, so even if something did crash (which hasn't happened to me), you wouldn't lose hours of work like you did with H&R Block. Given your focus on reliability over price, I think ProSeries would be a great fit for your situation.

Just wanted to add one more important point that hasn't been mentioned yet - the timing of when you receive your W-2G matters for tax purposes. If you win big late in December, you might not receive the W-2G until January of the following year, but you're still required to report that income on the tax return for the year you actually won the money. So if you hit a big parlay on December 28th, 2024, that income goes on your 2024 tax return even if DraftKings doesn't mail you the W-2G until January 2025. This is different from some other tax documents that follow when you receive the form rather than when the activity occurred. I've seen people get confused about this and accidentally report gambling winnings in the wrong tax year, which can cause issues with the IRS since they'll have the W-2G showing up in their system for the correct year. Also worth noting - if you're a professional gambler (rare, but it happens), the tax treatment is completely different and these W-2G thresholds don't apply the same way. But for casual bettors, the info everyone else shared is spot on.

Just to clarify something that might be causing confusion - the $600 AND 300x rule applies to each individual winning bet/session, not your cumulative activity for the year. So if you win $800 on a $5 bet (160x), no W-2G. But if you win $1,500 on a $5 bet (300x), you'd get a W-2G. However, DraftKings and other platforms are also required to issue a 1099-MISC if your total net winnings for the year exceed $600, regardless of whether any single bet triggered a W-2G. This is separate from the W-2G requirement. One thing I haven't seen mentioned is that different states may have their own reporting requirements too. Some states require platforms to report gambling winnings at lower thresholds than federal requirements. So depending on where you live, you might receive state tax forms even if you don't hit the federal W-2G threshold. Also, make sure you understand the difference between "net winnings" and "gross winnings" on your tax forms - it can be confusing when you're trying to reconcile everything at tax time.

Ruby, you're getting fantastic advice here! As someone who's been helping small business owners with tax questions for several years, I can confirm that cash method is absolutely the right choice for your situation. At $20k annual revenue, you're nowhere near the complexity threshold where accrual becomes beneficial. The cash method will save you significant time and mental energy that's better spent sourcing inventory and growing your sales. The inventory tracking everyone's mentioned is really the only "special rule" you need to worry about, and it's much simpler in practice than it sounds. Think of it this way: when you buy a $15 vintage jacket, that $15 isn't immediately deductible like your other business expenses. Instead, it becomes deductible only when that specific jacket sells - whether that's next week or next year. I'd recommend keeping a simple purchase log (even just a notebook) where you record the date, item description, and cost for everything you buy to resell. When items sell, you can reference back to find the original cost for your tax deduction. This system scales well as your business grows and keeps you compliant without unnecessary complexity. One often-overlooked benefit of cash method for resellers: it naturally smooths out your tax liability since you're only deducting inventory costs when you have the corresponding sales income. This can actually be advantageous for cash flow compared to deducting large inventory purchases upfront under accrual method. Stick with cash method + simple inventory tracking, and you'll have a system that works great for years to come!

Ruby, I can totally relate to your situation! I started a similar reselling business about 8 months ago and went through this exact same decision process. Everyone here has given you excellent advice about choosing cash method - I completely agree that's the right choice for your scale. What really helped me was realizing that the "inventory exception" isn't as complicated as it initially sounds. I keep it simple with just two rules: regular business expenses get deducted when I pay them (eBay fees, shipping supplies, gas for sourcing), but inventory costs only get deducted when each item actually sells. For tracking, I use a basic approach - I keep a small notebook in my car and jot down what I paid for each item right when I buy it, along with where I got it. When something sells later (sometimes months later!), I just flip back through to find what I originally paid. Takes maybe 30 seconds per purchase but saves me so much headache at tax time. The cash method has been perfect for my business - it matches how I naturally think about money flow, and tax prep is much more straightforward. At your revenue level, the simplicity definitely outweighs any theoretical advantages of accrual accounting. Focus on building good tracking habits now and you'll be set as your business grows!

I really appreciate everyone's detailed responses here! This is exactly the kind of guidance I needed. It sounds like my main mistakes were: 1. Both my wife and I claiming our child on our separate W-4s (should only be one of us) 2. Not completing Step 4c with the additional withholding amount from the Multiple Jobs Worksheet @Freya Larsen - your explanation about the child tax credit being claimed twice makes perfect sense now. No wonder we're underwithholding! I think I'll start with the IRS Tax Withholding Estimator that @QuantumQuest and @CyberNinja mentioned since it's free and seems to handle the complexity of dual-income situations automatically. If that doesn't work out or I run into issues, I might consider some of the other services mentioned. One follow-up question: when I update our W-4s, should I submit the changes right away or wait until the start of the next payroll period? I want to make sure we start withholding correctly ASAP but don't want to mess up any current payroll processing. Thanks again everyone - this community is incredibly helpful!

Great advice from everyone here! I went through this exact same situation a couple years ago and learned some hard lessons. One thing I'd add that hasn't been mentioned much - if you're making these W-4 corrections mid-year (like now in April), you might want to consider having a bit more withheld than the calculators suggest since you've already been underwithholding for several months. The IRS estimator and other tools assume you're starting fresh at the beginning of the year. Since you've potentially been underwithholding since January, you might need to "catch up" with slightly higher withholding for the remaining pay periods. Also, don't forget that if you end up owing more than $1,000 when you file next year, you could face underpayment penalties even if you fix your W-4 now. The IRS generally wants you to pay at least 90% of your current year tax liability or 100% of last year's liability (whichever is smaller) through withholding and estimated payments. Keep good records of when you made the W-4 changes - this documentation can be helpful if you need to explain any underpayment situations to the IRS later.