Ok I'm totally confused now. I have a W-2 from my employer AND a W-2 from the insurance company for the same health plan. Do I need to report both? Seems like double counting the same thing??

I'm dealing with this exact same situation right now! Got my regular W-2 from my employer plus this separate one for marketplace premiums they paid. Mine shows $3,600 in Box 1 with Social Security and Medicare taxes withheld but no federal income tax. Reading through all these responses has been super helpful - I had no idea this was taxable income until now. My HR department didn't explain any of this when they set up the marketplace coverage for me. I thought they were just being helpful by contributing to my health insurance, but now I realize I'm going to owe taxes on their "help." Has anyone here actually filed their return with both W-2s yet? I'm curious if TurboTax handles this smoothly or if there are any gotchas I should watch out for when entering the marketplace premium W-2. Also wondering if this affects my refund timing since it's technically additional income I wasn't expecting to report. Thanks everyone for sharing your experiences - this thread is way more helpful than the IRS website for understanding this situation!

Don't forget to double check that your name is EXACTLY the same on your tax return as it is with Social Security. Even small differences (like a hyphen) between your SS card and how you file can cause matching problems. The IRS matches against SS records, not just against what your broker has.

I went through this exact same situation last year with backup withholding due to a name mismatch issue. The stress of not being able to see those funds anywhere was terrible! One thing that really helped me was keeping detailed records of EVERYTHING - screenshots of my brokerage account showing the withholding, copies of all communications with my broker, and the corrected W-9 form I submitted. When I finally got my 1099-B in January, I made sure to file my taxes immediately to get that refund processed. The other advice I'd give is to set up direct deposit for your tax refund if you haven't already. With that much backup withholding, you're looking at a substantial refund, and direct deposit gets it to you much faster than waiting for a paper check. I got my $3,200 refund in about 10 days after e-filing. Also, even though others have mentioned you can skip quarterly payments, I'd recommend running the numbers yourself or with a tax professional to make absolutely sure. Better to be conservative than get hit with penalties later!

For what it's worth, I report everything regardless of the amount. $74 is so small it won't impact your overall tax situation much, but it does give you the opportunity to deduct mileage and other expenses related to that gig work. If you drove more than about 120 miles for those deliveries, you could actually show a loss on your Schedule C (using the standard mileage deduction of $0.625/mile for 2022), which could slightly reduce your overall tax bill.

Just an FYI - If you plan to do more gig work in the future, it's good practice to start tracking everything properly now, even for small amounts. Get a mileage tracking app, keep receipts for any expenses, and set aside about 25-30% for taxes. That way when you make more than $600 and DO get a 1099, you're already in the habit of doing things correctly.

Whatever software you choose, make sure you get one that properly handles the QBI (Qualified Business Income) deduction. With $41k in self-employment income, you should qualify for a pretty significant deduction there, and some of the cheaper software options don't calculate it correctly.

I switched to FreeTaxUSA this year after getting fed up with TurboTax's pricing and couldn't be happier. For someone with your income level and mix of W-2 plus freelance work, it's honestly perfect. The software handles multiple 1099s really well - I had 4 different clients this year and it was super straightforward to enter each one. What I love most is that it actually walks you through ALL the business deductions you might qualify for, including some I had no idea about like the QBI deduction that someone mentioned above. The price difference is insane - federal is completely free and state filing is only $15. I was paying TurboTax over $120 for the same thing. Plus their customer support is actually helpful when you have questions, unlike the nightmare of trying to get help from Intuit. One tip: make sure you keep good records of your business expenses throughout the year. FreeTaxUSA will help you categorize everything properly, but having organized receipts makes the whole process so much smoother.

Be careful... a friend of mine ignored a missing W-2 and got a CP2000 notice from the IRS about 8 months later. They calculated what he owed PLUS interest AND a 20% accuracy penalty. Ended up being WAY more expensive than just filing the amendment would have been. Just pay your tax guy or use one of the options others suggested. Not worth the stress of waiting for the IRS to catch it.

You absolutely need to file that amendment - don't even think about ignoring it! The IRS gets copies of all W-2s directly from employers, so they WILL catch this discrepancy eventually. It's not a matter of if, but when. I work in tax preparation and see this situation all the time. When clients try to "wait it out," they almost always end up paying more in penalties and interest than they would have spent on just filing the amendment properly. The IRS has automated systems that match W-2s to tax returns, and a $2,800 discrepancy will definitely trigger a notice. Here's what you need to know: File Form 1040-X as soon as possible. You'll likely owe additional tax on that $2,800 (probably around $300-600 depending on your tax bracket), plus you'll need to pay back part of your refund. But if you file the amendment before the IRS catches it, you'll avoid the hefty accuracy-related penalties that can be 20% of the underpayment. If $175 seems steep for your tax preparer, you can definitely do this yourself or use some of the tools others mentioned. The 1040-X form has pretty clear instructions, and since you're just adding income, it's relatively straightforward. Don't let the cost of fixing it now turn into a much bigger problem later!