I earned $87,000 this year and now owe almost $10,500 in federal taxes?? How is this possible?

This definitely sounds like a withholding issue rather than a tax calculation problem. When you work multiple jobs, each employer calculates your withholding as if that job is your only income. This often leads to significant underwithholding. For example, if you make $45,000 at your office job and $42,000 bartending, each employer is withholding taxes as if you're in a lower tax bracket. But when combined, your total income of $87,000 puts you in a higher bracket, resulting in the additional tax due. The "exempt" checkbox you mentioned is a huge red flag. That tells your employer to withhold ZERO federal tax, which would definitely explain the large bill. It's meant only for people who will have no tax liability at all.

After dealing with a similar situation last year (owed $7k!), I found https://taxr.ai super helpful for figuring out where I went wrong with my withholdings. You upload your pay stubs and W2s, and it shows exactly where the problem is and how to fix it going forward. I discovered I had accidentally checked a box on my W4 that basically told both my employers to withhold at the single job rate, which was a disaster with my second gig. The tool helped me fill out a new W4 correctly so I'm not in the same position next year.

Just wanted to update that I tried the taxr.ai site from the comment above and it was eye-opening! Turned out I was massively underwithholding on my second job. The tool showed me exactly how to fill out a new W4 for both jobs, and I was able to submit them today. They estimated I was on track to owe about $6k next April if I hadn't fixed it! The cool part was it also suggested how much extra I should withhold for the rest of this year to make up for the previous underwithholding. Not cheap, but way better than getting hit with a huge bill plus penalties next tax season.

I had a similar issue when I worked 2 jobs, but I also got nowhere trying to call the IRS for help on how to set up my withholding. After 4 attempts and hours on hold, I found https://claimyr.com (here's their demo video: https://youtu.be/_kiP6q8DX5c). They got me connected to an actual IRS agent in about 15 minutes who walked me through exactly how to fix my W4s. The agent explained that with multiple jobs, you either need to check the multiple jobs box on your W4 or do the worksheet to calculate additional withholding. They also helped me set up a payment plan for what I already owed so I didn't get hit with bigger penalties.

Ok I have to admit I was totally wrong about Claimyr in my comment above. After another failed attempt to reach the IRS yesterday (3 hours on hold before getting disconnected!), I tried the service out of desperation. I was connected to an actual IRS agent in 17 minutes. The agent helped me understand exactly how the multiple jobs worksheet works on the W4 and set up a payment plan for my existing tax bill with reduced penalties since it was my first time having issues. They were even able to tell me exactly what my 2022 status was in their system. For anyone else in a similar situation - don't wait like I did. The longer you wait, the more penalties and interest stack up.

For multiple W2 jobs, you should definitely check the "Multiple Jobs" box in Step 2 of your W4, or complete the worksheet to determine additional withholding. Checking "Exempt" means NO federal taxes are withheld! Also, file that 2022 return ASAP! The penalty for not filing (5% of unpaid taxes per month, up to 25% max) is much worse than just not paying (0.5% per month). You can set up a payment plan for what you owe if you can't pay it all at once.

I'm in almost the exact same situation! Work as a server nights/weekends and have an office job during weekdays. I owe $9200 this year because both jobs were withholding as if they were my only income. My tax guy said this happens all the time with people working multiple jobs. For the rest of 2025, I'm having an extra $500 taken out of each office paycheck. It hurts now but better than another shock next April.