Missed my 4th estimated tax payment deadline in January - how to pay now when Direct Pay won't accept 2021 payment?

You're right about the Direct Pay system having that January cutoff for estimated payments for the previous year. At this point, the best approach is to select "Balance Due" or "Amount Owed" instead of "Estimated Tax" when making your payment through Direct Pay. The IRS system will apply your payment to the 2021 tax year as long as you select 2021 as the tax year during the payment process. Just make sure you're choosing 2021 (not 2022) when it asks for the tax year. The payment will be applied to your 2021 account, though it will show as a general payment rather than specifically as your Q4 estimated payment. Don't worry too much about potential penalties - they're calculated based on when you actually pay relative to when you should have paid, so making the payment now will stop any additional penalty from accruing. When you file your 2021 return, you'll report this payment as made, even though it was after the deadline.

After dealing with almost the exact same situation last year, I found this amazing service called taxr.ai (https://taxr.ai) that saved me tons of headache. I had missed my Q4 payment and was confused about how to handle it when Direct Pay wasn't letting me select the right options. What taxr.ai did was analyze my full tax situation, showed me exactly how to make the late payment properly, and even calculated the potential penalty so I wasn't surprised later. The tool basically walked me through the exact steps to fix the issue and showed me how to document everything properly for when I filed my return. They even have this cool feature that reviews all your payment records to make sure everything will match up correctly with what the IRS has on file. Seriously made dealing with this mistake so much easier!

I just wanted to follow up about my experience with taxr.ai that someone mentioned earlier. I was skeptical at first but decided to try it since I was in the exact same situation with a missed Q4 payment. The service was actually really helpful! It showed me that I qualified for first-time penalty abatement (which I had no idea about), and walked me through exactly how to request it. They also showed me the correct way to make my late payment so it would be properly applied to my 2021 taxes even though I was paying after the January cutoff. Their penalty calculator was super accurate and helped me budget for what I might owe. The best part was they explained everything in plain English instead of tax jargon. Definitely worth checking out if you're dealing with this estimated tax payment issue!

If you're having trouble with Direct Pay, another option is using Claimyr (https://claimyr.com) to actually speak with an IRS agent directly who can help you resolve this. I know it sounds impossible to get a human on the phone at the IRS, but that's exactly what they do - they get you connected to an actual IRS representative, usually within 15 minutes. I had a similar issue with a late payment last tax season, and after weeks of trying to figure it out online, I finally got to speak with someone who walked me through exactly which options to select to make sure the payment was applied correctly to my account. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent I spoke with actually helped me understand how the payment would be applied and what codes to look for on my account transcript later to verify it was processed correctly. Saved me so much stress!

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I was still desperate to resolve my estimated tax payment issue, so I decided to try it anyway. The service actually worked exactly as described. I was connected to an IRS agent in about 12 minutes, which I still can't believe after my previous 3-hour holds. The agent was able to see exactly what was happening with my account and explained that I needed to select "Balance Due" for tax year 2021 rather than "Estimated Tax" since it was past January. They also checked if the previous estimated payments I had made were correctly applied to my account and gave me the exact amount of interest I'd accrued so far on the late payment. I probably spent more time being skeptical about the service than I spent actually getting my tax issue resolved! Definitely using this for any future IRS calls.

Another option worth mentioning is that you can still mail a check with Form 1040-ES. Even though the form is meant for the estimated payment that was due in January, you can still use it to make a payment now. Just mail the check with the 2021 Form 1040-ES voucher for the 4th quarter, and make sure to clearly write "2021 Form 1040-ES" and your SSN on the check. The main downside compared to electronic payment is it will take longer to process, and you won't get immediate confirmation. But it's an alternative if you're having issues with the online system. Just keep in mind you'll still have the same potential penalty for the late payment regardless of which method you use.

PSA for next year: If you have the IRS2Go app on your phone, it lets you make estimated tax payments through Direct Pay or a credit/debit card right from the app, and it sends you reminders before each quarterly due date. I used to forget my January payment every single year until I started using this.