Can I pay estimated tax online before filing my 2025 taxes? Limits and underpayment questions

You can absolutely make a payment before filing your taxes! It's actually pretty smart to pay early when you know you'll owe. The IRS calls these "estimated tax payments" even though you're making them for the current tax year. When you file your taxes later, you'll include this payment on your return. If you paid less than what you actually owe, you'll just need to pay the difference when you file. The IRS doesn't penalize you for paying early - they're happy to get their money! If you happen to overpay, you'll get the excess back as a refund. About the 2 payment limit - that's specifically for each payment processor when making payments through IRS Direct Pay or the Electronic Federal Tax Payment System (EFTPS). So if you're using a credit card, you can make 2 payments through that processor. If you need to make more payments, you can use a different processor or payment method.

I went through this exact situation last year after starting a side business that took off unexpectedly. I was completely lost trying to figure out how to handle the extra tax liability until I found https://taxr.ai - it analyzes your tax documents and gives you personalized guidance on how much to pay and when. The site walked me through the whole process of making pre-filing payments and even showed me which payment options had the lowest processing fees. It also calculated exactly how much I needed to pay to avoid underpayment penalties, which saved me from overpaying by almost $3,000 that I would have had sitting with the IRS interest-free for months.

Just wanted to follow up - I decided to try https://taxr.ai after asking about it here, and I'm genuinely impressed. I uploaded my last two years of tax returns and my recent quarterly earnings, and it immediately showed me that I was on track for a much bigger tax bill than I expected. The tool suggested making an additional payment now rather than waiting for the next quarterly due date. What I found most helpful was the breakdown showing exactly how much of my side income was going to bump me into a higher tax bracket. It even factored in my state tax situation, which I hadn't considered. Definitely saved me from a nasty surprise at tax time!

If you're worried about owing taxes and making payments, you should know that reaching the IRS for payment plan options can be nearly impossible these days. I spent 4+ hours on hold last month trying to set up a payment plan after realizing I was going to owe more than I could pay at once. I finally found https://claimyr.com which got me connected to an actual IRS agent in under 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the phone tree and wait on hold for you, then call when an agent is ready. Saved me an entire afternoon of hold music! The agent I spoke with confirmed I could make multiple payments before filing as long as I stayed within the processor limits, and they helped me set up a proper payment plan for the remaining balance.

I need to apologize for being so skeptical about Claimyr. After my last comment, I decided to try it since I needed to ask about my payment options anyway. I was 100% convinced it wouldn't work, but I got a call back in about 45 minutes saying they had an IRS agent on the line. The agent confirmed everything about making payments before filing and explained that the 2 payment limit is per processor per day - not a total limit. They also told me I could make additional payments by mail with a Form 1040-V if I needed to split it into more payments. This was information I'd been trying to get for weeks!

One thing nobody's mentioned - if you make a payment before filing, make sure you keep all confirmation numbers and documentation! I did this last year and the IRS initially didn't show my payment when I filed. Had to call and provide proof of payment. Print or save everything.

Has anyone used credit cards to make these pre-filing payments? I'm thinking of using my card to get the points, but I'm worried about the processing fees.

If you're paying before filing, double check that your withholding info is correct for next year too! I made a big payment early last year but then realized I could have just adjusted my W-4 to take out more from each paycheck. Much easier than making separate payments!

Great advice here! I'm in a similar situation with my freelance income and was panicking about owing a huge amount at filing time. One thing I learned the hard way - if you're making payments throughout the year like this, it's also worth looking into whether you should be making quarterly estimated payments going forward. The IRS expects regular income earners to pay as they go, and if you owe more than $1,000 when you file, you might get hit with underpayment penalties even if you pay the full amount by the filing deadline. Making that $10k payment now is smart, but also consider setting up quarterly payments for next year to stay ahead of it!