A bit off topic, but what happens if your income is right on the edge between two brackets? Like literally the last dollar puts you over?

This is such a great question and I'm glad someone asked it! I was completely baffled by this same thing when I first started really paying attention to my taxes. What really helped me understand it was looking at the actual dollar amounts. For 2024, the 12% bracket for married filing jointly goes up to about $89,450, and then the 22% bracket starts. So if you and your spouse make $95,000 combined, only about $5,550 of your income gets taxed at 22% - the rest is taxed at the lower rates. I think the psychological impact of seeing "22%" makes it feel way scarier than it actually is. When I calculated my actual effective tax rate (total taxes divided by total income), it was much lower than that 22% number that was freaking me out. The historical context others mentioned is spot-on too. Before 2017, we had a 15% bracket that jumped to 25%, so the current 12% to 22% is actually a bit of an improvement for most middle-class families, even though it still feels like a big jump.

Don't forget you can deduct a percentage of your cell phone bill as a business expense for food delivery! Since you need your phone for the app, navigation, customer communication, etc. Just calculate what percent of your phone usage is for delivery work (be honest - the IRS isn't stupid). I claim about 60% of my phone bill since I use it a ton for deliveries. Also, those insulated bags, car phone mounts, and even a portion of car insurance can be deductible! Just make sure to keep all receipts.

I use TurboTax Self-Employed for my delivery gig taxes and it's pretty straightforward. It walks you through all the possible deductions for delivery drivers. Just make sure to keep good records all year - the IRS has been cracking down on gig workers lately with all the new reporting requirements. The apps are supposed to issue 1099s for anyone making over $600 now, so there's no flying under the radar anymore. I learned the hard way after a messy audit last year!

Don't forget to make copies of EVERYTHING before you mail it! I learned this the hard way when the IRS claimed they never received my 2019 return. No proof = had to redo everything + paid penalties.

Just a heads up for anyone considering these different options - I recently had to mail past returns for 2019-2021 and ended up using a combination approach that worked really well. First, I weighed each complete return package at the post office (they'll do this for free) to get exact postage amounts. My 10-page returns with supporting docs were actually closer to 3 ounces each, so needed 3 stamps per envelope rather than the 2 mentioned earlier. For the mailing method, I went with certified mail with return receipt for the peace of mind, but here's a tip: you can do this online through USPS.com and print the labels at home. It's slightly cheaper than doing it at the counter and you avoid the lines. Most importantly, I called the IRS practitioner priority line first (different number than the regular taxpayer line) to confirm which processing center to use for each year. Turns out the addresses had changed for my state between some of those years. The wait was still long but not as bad as the regular line. Total cost was about $12 per return (postage + certified mail + return receipt) but having tracking numbers and delivery confirmation was absolutely worth it. All three returns were processed without issues and I got confirmation within 6 weeks.

Anyone know if the IRS will send confirmation when they receive your payment? I'm in a similar situation and it would be nice to get some notification that they got my check.

I went through this exact same panic last year! You absolutely did the right thing by sending your payment to Cincinnati. The IRS has a very specific system - payments with Form 1040V go to their payment processing centers (like Cincinnati), while actual tax returns go to document processing centers (like Fresno). I made the mistake of overthinking it and almost sent my payment twice because I was so worried. Don't do that! The IRS will match your payment to your return using your SSN and other identifying information. It's actually a pretty reliable system once you understand how it works. One tip: if you want peace of mind, you can set up an online account at IRS.gov. Once your payment is processed (usually 3-4 weeks), it will show up in your account transcript. That's how I confirmed mine went through properly. You're going to be just fine!

Just to add another perspective - this exact situation is why I switched from FreeTaxUSA to TaxSlayer last year. I had a similar pension-to-Roth conversion and FreeTaxUSA didn't handle it correctly, while TaxSlayer had a specific question about Roth conversions that made it super easy. Not saying you need to switch software, but if the override options others suggested don't work, it might be worth considering. The IRS definitely expects you to pay tax on this conversion regardless of what code is on the form.

Mason, I went through something very similar with a 403(b) to Roth conversion last year. The key thing to understand is that Code G is definitely wrong for your situation - that's supposed to be for trustee-to-trustee transfers between similar account types where no taxes are due. What you had was a conversion from a traditional pension (pre-tax money) to a Roth IRA (after-tax account), which absolutely should be taxable. The pension administrator should have used Code 2 or Code 7 depending on your age and circumstances. For FreeTaxUSA, when you're entering the 1099-R, after you input all the box information, it should take you to a series of follow-up questions. One of them asks about what you did with the money - look for an option that says something like "I converted it to a Roth IRA" or "I rolled it to a different type of account." Selecting that should override the Code G treatment. If you can't find that option, definitely call FreeTaxUSA support - they deal with this exact scenario all the time and can walk you through the override process. Don't file without getting this fixed because you're right that the IRS will expect taxes on this conversion.