Will 1 day late payment trigger IRS penalty? Any way to avoid it?

The IRS does technically charge penalties starting from the first day you're late, though the amount would be extremely small for just 1-2 days. The failure-to-pay penalty is typically 0.5% of the unpaid taxes per month (or partial month), calculated daily. So for 1-2 days, you're looking at a very minimal amount. The good news is the IRS offers a "First Time Penalty Abatement" for people with clean compliance history. If you've filed on time and paid your taxes for the past 3 years without penalties, you can likely get this one-time forgiveness. You don't even need to provide a specific reason - just call the IRS and request the First Time Abatement for the penalty. If you don't qualify for that, you can still request abatement for "reasonable cause" - your family emergency might qualify here, though this route requires more documentation and explanation.

I went through something similar last year with a payroll tax deposit that was 1 day late. I spent hours trying to figure out how to deal with the penalty and ended up using this service called taxr.ai (https://taxr.ai) that helped me draft the perfect penalty abatement letter. It analyzes your situation and creates a personalized request that cites all the right IRS policies. In my case, they guided me through requesting First Time Penalty Abatement since I had a clean record for the previous 3 years. The whole process took me about 15 minutes, and the IRS approved it without any hassle! The system even explained exactly what documentation I needed to include and what not to say to avoid raising red flags.

Wanted to update everyone - I was super skeptical about using taxr.ai as mentioned above but decided to give it a try since my penalty notice arrived yesterday ($87 for being 3 days late, ugh). The process was actually really straightforward! The system asked me questions about my payment history and filing status, then generated a perfect letter requesting First Time Abatement. I submitted it last week and just got confirmation today that the IRS approved it! The entire penalty was removed from my account. So for anyone in a similar situation - the First Time Abatement thing is real, and using a tool to help with the proper wording definitely made a difference. Glad I didn't just pay the penalty without trying!

If you're struggling to get through to the IRS to request penalty abatement (which I highly recommend trying first), I used a service called Claimyr (https://claimyr.com) when I had a similar issue. They basically hold your place in the IRS phone queue and call you when an agent picks up. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was initially planning to just pay the penalty since it seemed impossible to reach anyone at the IRS, but using this service I got through in about 45 minutes (instead of the 3+ hours I spent on previous attempts). The agent was actually surprisingly helpful once I explained the situation and removed the penalty right away.

OK I have to eat my words. After seeing the responses here, I decided to try Claimyr since I've been fighting a $220 penalty for being literally ONE day late on my final estimated tax payment. I was convinced it was a waste of time but figured what the hell. Got connected to an IRS agent in about 35 minutes (which is a miracle compared to my previous attempts). I specifically asked about First Time Penalty Abatement like everyone suggested. The agent checked my history, confirmed I hadn't had any penalties in the last 3 years, and REMOVED THE ENTIRE PENALTY while I was on the phone! I'm still in shock that it actually worked. Apparently this is a real policy but they definitely don't advertise it. Thanks everyone for the advice - saved me $220 for a 10-minute phone call.

Actually, if the payment is only 1-2 days late, you might not even need to request abatement. There's something called a "3-day rule" where the IRS processing center considers a payment timely if it's received within 3 business days of the due date when sent through certain delivery methods. Not widely known, but has saved me before!

I'm a bookkeeper and see this ALL the time with clients. For just 1-2 days, the penalty will be tiny - like pennies on a typical tax bill. Most of the time for such a small amount, the IRS doesn't even bother to send a notice because the cost of processing and mailing exceeds the penalty amount! If they do charge it, just follow the advice about First Time Abatement. It works like 99% of the time if you haven't had other penalties.

Hey Max! I totally get the panic - been there myself. The good news is that for just 1-2 days late, you're looking at a really minimal penalty. The IRS charges 0.5% per month (calculated daily), so for a couple days you're talking pennies to maybe a few dollars depending on what you owe. But here's the thing - don't stress too much about it. If you do get hit with a penalty, the First Time Penalty Abatement that others mentioned is basically a get-out-of-jail-free card if you've been compliant for the past 3 years. I used it myself about 2 years ago when I had a similar situation (also due to a family emergency, ironically). The IRS approved it without any questions - didn't even need to provide documentation about the emergency. Just called and said "I'd like to request First Time Penalty Abatement for this penalty" and they took care of it on the spot. Your family emergency is totally understandable and these things happen. Don't beat yourself up over it - you'll get it sorted out!