That's a good point I hadn't considered! I'm pretty sure I'm taking the standard deduction in both cases since my mortgage interest and charitable donations probably don't add up to enough to itemize, but I should double check. As for state taxes, I'm in Texas so we don't have state income tax, which makes things a bit simpler. Do you think that could still be affecting the calculation somehow?

If you're in Texas with no state income tax, then that eliminates one possible source of discrepancy. That's actually helpful for narrowing down the issue. Even if you're taking the standard deduction, check if both systems are using the correct amount for your filing status. The standard deduction for single filers is $13,850 for 2023 tax year. If H&R Block somehow miscategorized your filing status, that could explain part of the difference. Another area to check is qualified retirement contributions. Sometimes tax software requires you to manually enter 401(k) contributions even if they're shown on your W2. If H&R Block missed those, it would calculate a higher taxable income than the IRS calculator.

This is solid advice! Line-by-line comparison is tedious but effective. I work in payroll and Box 12 codes cause the most confusion with tax software. Codes D, E, F, G, H and S all relate to different types of retirement contributions and sometimes software doesn't categorize them correctly.

Thanks for the suggestions! I checked and my withholding percentage definitely dropped. Looking at box 2 of my W-2, last year they withheld about 18% of my total income but this year it's only 15%. That seems to be where the problem is. The bonus was about $8500 so that explains a good chunk of the difference.

Yeah that withholding percentage drop is definitely your answer. For the bonus specifically - they typically withhold a flat 22% from bonuses (called supplemental wages), but if you're in a higher bracket overall, that's not enough. If you expect similar bonuses in the future, you can add an extra withholding amount on line 4(c) of your W-4. Calculate roughly how much more you'd need based on your actual tax rate minus the 22% they'll withhold automatically.

Does your company let you do this? Mine requires submitting W-4 changes like 3 weeks in advance so it's hard to time it exactly with the bonus paycheck.

Yeah my company lets us make W-4 changes through our online portal and they take effect in the next pay cycle. I just mark myself as "Married but withhold at higher Single rate" and add 0 dependents instead of my usual 2 for the bonus check. I've also started just having an additional $50 withheld from each regular paycheck throughout the year (line 4c on the W-4) which builds a little cushion. I'd rather get a small refund than owe.

Thank you for the suggestion! I definitely don't want to do anything illegal. Would these credits help even if he doesn't make much money? He works part time and gets some cash jobs on the side (probably doesn't report all of that income).

Yes, these credits can definitely help people with lower incomes! The Earned Income Tax Credit (EITC) is specifically designed for lower-income workers and is refundable, meaning he could get money back even if he owes no tax. Regarding the unreported cash income - that's a separate issue, but he should know that claiming tax credits while not reporting all income could create problems if he's audited. The safest path is to report all income and claim the credits he's legally entitled to.

No, if he doesn't claim his daughter as a dependent, he can't file as head of household. He'd have to file as single, which has worse tax rates and a lower standard deduction. That would probably hurt him more financially than whatever benefit OP might share from illegally claiming the kid.

Thanks for explaining that. Makes sense why he'd want someone else to claim his kid if he's not making enough to benefit from the credits, but sounds like he'd lose the head of household status which is pretty valuable.

How do you handle insurance and registration for the 100% business car? Do you put that in your business name? My insurance was weird about covering a personal vehicle used primarily for business.

I have the business vehicle registered and insured under my LLC name with a commercial auto policy. You're right that it can be tricky with personal policies - many won't properly cover business use or will charge extra. The commercial policy actually ended up being around the same price after shopping around, and it provides better coverage for my situation. The registration in the business name also makes it clearer to the IRS that it's a dedicated business asset. One thing to note though - if you go this route, you need to be disciplined about never using that vehicle for personal trips, not even stopping for personal errands during business trips.

Did you have to pay a higher rate for a business lease vs a personal one? I looked into this and the dealer wanted to charge me more when I mentioned it was for my business.

Thank you for this advice! I definitely need to fix this for next year. How do I calculate how much to pay for quarterly estimated taxes? And where exactly on the W4 do I add extra withholding?

For estimated quarterly taxes, you can use the worksheet that comes with Form 1040-ES. Basically, you estimate your total tax liability for the year and divide by four. Pay special attention to your 1099 income - you generally need to set aside about 30-35% of that for taxes (15.3% for self-employment tax plus your income tax rate). For the W4, look at Step 4(c) "Extra withholding." You can put any additional amount you want withheld from each paycheck. If you have multiple W2 jobs, there's also a "Multiple Jobs Worksheet" that can help calculate this more precisely. Your HR department should be able to provide you with a new W4 form to update this information.

I amended last year and it was actually pretty easy. Just file Form 1040-X and include any updated forms that changed. FreeTaxUSA can help you prepare an amended return too. Just be aware that processing times are really slow right now - mine took about 4 months.