Is the DirectPay system pretty straightforward to use? And would I need to file any forms or just make the payment?

DirectPay is super easy to use - just go to IRS.gov and look for the "Pay" button. You'll need basic info like your SSN, name, address, and bank info (routing/account numbers). No forms needed to make the payment itself. You should still fill out the 1040-ES worksheet for your own records to calculate the correct amount, but you don't have to mail that in if you pay online. The system will give you a confirmation number - keep that for your records. Come tax time next year, you'll report this payment on your 1040 as estimated tax paid.

This is the approach I use! Way simpler than trying to calculate exact quarterly payments. I just make sure my withholding covers last year's tax bill and then I don't worry about my side hustle income until tax time.

Thanks for the advice! One question - if I pay online now before filing, how do I make sure the payment gets matched to my return when I eventually mail it?

When you make a payment through the IRS Direct Pay system, you'll select the reason for payment (in your case "extension" or "tax return"), the tax year (2022), and provide your identifying information like SSN. The IRS will automatically match your payment to your return when it's processed based on this information. Make sure to print the confirmation page after making your payment and keep it with your tax records. If there's ever a question, this confirmation serves as proof that you paid on time, even if your return is processed later.

The Non-Filer tool is actually designed for people who aren't required to file a return but need to register for specific benefits or credits. It's not appropriate for someone who has a regular tax filing obligation like the OP who has already prepared their return. Using the Non-Filer tool when you actually should be filing a complete tax return can create complications in the IRS system and potentially flag your account. The OP should either mail their completed return or work with a tax professional to efile it.

Is Cash App Taxes really completely free? No hidden fees for filing state returns or anything? Seems too good to be true compared to paying $70+ with H&R Block.

Yes, it's actually completely free for both federal and state returns. No hidden fees or surprise charges. They make their money from the Cash App ecosystem and other financial services they offer, not from the tax preparation. The catch (if you want to call it that) is that it doesn't support some more complex tax situations like multiple state filings or foreign income. But for a basic married filing jointly return with W-2 income, it handles everything perfectly. I've used it for two years now with no issues and got my refunds quickly both times.

I used TaxSlayer last year after switching from H&R Block. It was about $30 cheaper for my situation (married filing jointly with a mortgage). The interface is decent but not as polished as H&R Block. It got the job done though and my refund amount matched what I was expecting.

Yikes, that's exactly what I'm afraid of! Did they hit you with a big penalty? I'm definitely not trying to do anything that would trigger an audit... Thanks for the warning!

The penalty wasn't huge - about 20% on top of what I owed back - but I also had to pay interest on the unpaid amount. The bigger headache was going through the entire audit process, which was stressful and time-consuming. The agent actually wasn't mean about it since it's such a common misunderstanding. He explained that even though my employee handbook required me to wear Buckle clothes, they're still considered regular street clothes suitable for everyday wear. The test isn't whether they're required, but whether they could reasonably be worn outside work.

I work at a high-end jewelry store, and we can deduct our required black suits because we're specifically prohibited from wearing them outside work (it's in our contract). But that's different from regular retail clothes that you'd wear anyway.

Thank you so much for this warning about not rolling it into our own accounts! I honestly might have tried to do that thinking it would simplify things. Do you happen to know if we can just start taking the correct distributions now, or do we need to "catch up" on all the ones we missed over the past years?

You don't need to "catch up" by withdrawing all the missed distributions at once. You should calculate what you should have taken each year, but going forward you just need to start taking the correct annual distributions based on the appropriate life expectancy table. What you DO need to do is file Form 5329 for each year you missed a distribution, request the penalty waiver on each form, and include a letter explaining that you didn't understand the RMD requirements. Then start taking the correct annual distribution this year. Most financial institutions that hold IRAs can help calculate your required distribution amount.

I used H&R Block software (not the in-person service) last year to handle my missed RMDs on an inherited IRA. It worked fine for generating the 5329 forms, but it didn't help with the waiver request letter or calculating what my distributions should have been. I ended up having to research those parts separately.

Thanks for sharing your experience! Sounds like I might need some additional help beyond just the tax software to get the calculations right. I'll look into what supplemental services might help with those calculations while still using the software for the actual filing.