How is Box 1 on W-2 calculated? Need simple explanation for what's included/excluded

So if I'm understanding correctly, Box 1 is basically what I'm being taxed on by the feds? Does that mean the amounts in Box 3 (Social Security wages) and Box 5 (Medicare wages) are different because some deductions are taxable for those purposes but not for regular income tax?

That's exactly right. Box 1 is what's subject to federal income tax. Boxes 3 and 5 will likely be different because not all pre-tax deductions are exempt from Social Security and Medicare taxes (commonly called FICA taxes). For example, your 401(k) contributions are exempt from federal income tax (not in Box 1) but are still subject to FICA taxes (included in Boxes 3 and 5). Health insurance premiums are typically exempt from all taxes, so they're not included in Boxes 1, 3, or 5. That's why Box 1 is usually the lowest number, and Boxes 3 and 5 are often higher.

Does it work with other tax forms too? I'm confused about some numbers on my 1099-MISC and don't even know where to start.

I'm skeptical about putting my tax documents into some random website. How secure is this thing? And can it really explain stuff better than just googling what each box means?

Yes, it works with basically all tax forms including 1099s. It's particularly helpful with those because the rules for self-employment income can get complicated fast. The security is actually really good - they use bank-level encryption and don't store your documents after processing. And yes, it's way better than Google because it analyzes YOUR specific numbers rather than giving generic explanations. It pointed out that my employer had accidentally included some non-taxable reimbursements in Box 1 that I would have never caught otherwise.

Wait, there's actually a way to talk to a real person at the IRS without wasting your entire day on hold? How does that even work? I thought getting through to them was basically impossible during tax season.

Yeah right, sounds like a scam. Why would I pay some third party just to call the IRS for me? I bet they just put you on hold anyway and charge you for the privilege.

It basically calls the IRS repeatedly using their system and navigates the phone tree for you. Once they get a human on the line, they call you and connect you directly. It saves you from having to redial hundreds of times or wait on hold for hours. The service is specifically designed for tax season when it's nearly impossible to get through. I was skeptical too until I tried it - I had been trying to get through on my own for days with no luck. With this, I was talking to an actual IRS rep in about 15 minutes. They don't just put you on hold - you literally only get called when there's a live person ready to speak with you.

Do health savings account (HSA) contributions work the same way? I put like $200 per month into mine through payroll deductions but don't know if that's pre-tax or post-tax.

Yes, HSA contributions made through payroll deductions are pre-tax and work exactly the same way. Your $200/month ($2,400/year) wouldn't be included in Box 1. It's one of the best tax advantages out there since HSA money is never taxed if used for qualified medical expenses - it goes in pre-tax, grows tax-free, and comes out tax-free for medical costs.

This is brilliant advice! Just checked my December paystub and it has a "YTD Fed Taxable Wages" column that matches Box 1 perfectly. Never thought to look there. My paystub even breaks down all the pre-tax deductions with YTD totals which explains the exact difference between my gross salary and Box 1.