I think there's some confusion here. I run an LLC too and I have to get W-9s from all my clients before I can work with them. My accountant said it's required!!

I went through this exact same confusion when I transitioned from solo contractor to LLC with employees! The key thing to remember is that W-9s flow in the direction of payments - you collect them from people you PAY, not from people who pay you. As an LLC with employees and contractors, here's what you need to do: 1. Collect W-9s from your independent contractors (before you pay them) so you can issue 1099-NECs if you pay them $600+ annually 2. Have your own completed W-9 ready to provide to clients who request it (usually larger businesses that might need to issue you a 1099) 3. You generally don't need W-9s from regular customers who buy your products or services The confusion often comes from remembering when you were a solo contractor - back then, you were providing YOUR W-9 to the businesses that hired you. Now that you're the business owner, the roles have flipped. You're collecting W-9s from contractors you hire, and providing yours only when clients specifically request it. This is a really common point of confusion for growing businesses, so don't feel bad about needing clarification!

One thing that might help clarify this - think of it as two separate tax systems that don't really "talk" to each other during the calculation process. Your federal tax is calculated on your full gross income ($135k in your case), and your state tax is also calculated on that same gross income. The only place they interact is if you choose to itemize deductions on your federal return, where you can deduct up to $10,000 of state and local taxes paid. But with the current standard deduction amounts, most people come out ahead just taking the standard deduction anyway. So to directly answer your question - neither is calculated "first." They're calculated independently on your gross income, and then you get to choose the most beneficial approach (standard vs itemized) when filing your federal return.

Just to add some practical perspective here - I went through this exact confusion when I started making similar income. The key thing that helped me was realizing that your employer's payroll system handles the withholdings simultaneously, but your annual tax liability is calculated separately for each jurisdiction. For planning purposes at your $135k income level, you'll likely pay federal tax on the full amount (after standard deduction of around $14,600 for 2025), and state tax on the full amount too. The withholdings from your paycheck should roughly balance out what you owe when you file, assuming your W-4 is filled out correctly. One tip: if your state tax rate is 9.5% like you mentioned, you might want to run the numbers on itemizing vs standard deduction. With high state taxes plus any mortgage interest, charitable donations, etc., you could potentially exceed the standard deduction threshold and benefit from itemizing (which would let you deduct up to $10k of those state taxes).

I went through almost the exact same situation last year with a large bonus and back pay! The key insight from @Thais Soares is spot on - the IRS calculator often double-counts bonuses if you enter them both in your YTD totals AND in the separate bonus section. Here's what worked for me: I only included my bonus/back pay in the YTD earnings and YTD withholding amounts, but left the bonus section blank. This gave me a much more realistic picture of what I actually owed. Also, since you mentioned you prefer getting a refund rather than owing - consider that bonuses are typically withheld at the 22% supplemental rate, which might actually be higher than your regular tax bracket. If you had ANY federal withholding on those special payments, you're probably in better shape than the calculator initially showed. One more tip: make sure you're entering your 401k, HSA, and other pre-tax deductions correctly. These can significantly reduce your tax liability, especially when you have a higher income year due to bonuses. Don't panic about the $9,000 figure - that's almost certainly an error in how the data was entered. Try the method @Thais suggested and I bet you'll see a much more reasonable number!

I just wanted to add another perspective as someone who works in payroll - the confusion you're experiencing with the IRS withholding estimator is incredibly common, especially when bonuses are involved. One thing that might help is understanding that when you received your bonus and back pay, your payroll system likely treated them as "supplemental wages" and withheld at the flat 22% rate (or possibly used the aggregate method if they were combined with regular pay). This is actually separate from your regular withholding calculation. The issue many people run into with the estimator is that it's trying to project your entire year's tax situation, but it can get confused when you have irregular payments that were already subject to different withholding rules. Before making any drastic changes to your W-4, I'd suggest running the numbers one more time using the method @Thais Soares and @Taylor Chen mentioned - include everything in your YTD totals but don't double-enter the bonus. Also, grab your most recent paystub and make absolutely sure you're entering your year-to-date federal withholding correctly, including what was taken from those special payments. If you're still getting scary numbers after that, it might be worth having a tax professional take a quick look at your situation. Sometimes a fresh set of eyes can spot an input error that's throwing everything off.

I filed an estate tax return using Turbo Tax last year and regretted it. The software doesn't explain the complex interplay between estate administration expenses and income distribution deductions. I ended up having to amend the return after learning I could have saved about $3,200 in taxes by making different elections.

Based on what you've described with your uncle's estate - the house, investments, and business sale - I'd strongly recommend going with a CPA for at least this first filing. Estate tax returns involve some tricky concepts that even experienced individual tax filers can struggle with. The business sale proceeds alone could involve depreciation recapture, capital gains calculations, and potentially installment sale treatment depending on how it was structured. With three beneficiaries, you'll also need to navigate income distribution deductions and make strategic decisions about when and how much to distribute to minimize the overall tax burden. I made the mistake of trying to handle my father's estate return myself using tax software and ended up costing the estate thousands in missed deductions and suboptimal elections. A good CPA who specializes in estates will often save more than their fee through proper tax planning. You can always learn from working with them this year and potentially handle simpler future filings yourself once you understand the process better. As executor, your fiduciary duty is to maximize the estate's value for beneficiaries - sometimes that means spending money on professional help upfront.

I went through almost the exact same situation two years ago! Here's what I learned that might help: The most likely scenario is that someone made an honest mistake with SSN digits - it happens way more than you'd think. My case turned out to be a grandparent who transposed two numbers when entering their grandchild's SSN and accidentally used my daughter's number instead. Since you're the custodial parent (your son lives with you 70% of the time), you have the automatic legal right to claim him regardless of any informal agreements. You don't need Form 8332 - that's only for when YOU want to release your claim to your ex in future years. Here's exactly what worked for me: 1. File your return on paper claiming your son 2. Include a brief letter explaining you're the custodial parent and it's your agreed-upon year to claim him 3. Attach documentation showing he lives with you primarily (school enrollment, medical records, etc.) 4. Send it certified mail with return receipt The IRS processed mine in about 10 weeks and I got my full refund including the Child Tax Credit. They also sent a notice to whoever incorrectly claimed my daughter, so the mistake got corrected on both ends. Don't stress too much about this - as the custodial parent, the law is heavily in your favor!

I'm dealing with a very similar situation right now! My daughter was claimed by someone else even though it's clearly my year according to our custody agreement. This thread has been incredibly helpful - I had no idea about the custodial parent automatically having the right to claim regardless of agreements, or that Form 8332 is only needed when releasing that right to the non-custodial parent. The SSN transposition error theory makes so much sense too. I was convinced it had to be identity theft or my ex lying to me, but an honest mistake by some random taxpayer is actually much more likely. I'm going to follow the advice here about paper filing with documentation. Does anyone know if utility bills showing my address with my daughter's name (like for her cell phone) would count as acceptable proof that she lives with me? I have school records too, but I want to include as much evidence as possible. Also, for those who successfully resolved this - did you include copies of your custody agreement or divorce decree with your paper filing, or just focus on documents proving residence?