What's the most effective way to ask the IRS to waive a late filing penalty?

I've worked in tax resolution for years, and this is definitely something you can handle yourself. For a first-time penalty like this, the IRS often grants what's called "First-Time Penalty Abatement" if you have a clean compliance history (which sounds like you do if you've never had issues before). For the fastest resolution, I'd recommend calling the IRS at the number on your notice. While you might be on hold for a while, you'll get an immediate decision in most cases. Have your notice, EIN, and tax return information handy when you call. When you speak with the representative, simply explain that this was your first year with an LLC, there was confusion about filing deadlines, and you've always filed and paid on time previously. Be polite but direct in asking for the "First-Time Penalty Abatement" specifically. If you prefer writing, send a letter referencing your notice number and specifically request first-time penalty abatement. Include that you've had a history of compliance and this was your first partnership return. Mail it to the address on your notice with certified mail so you have proof of delivery.

I was in a similar situation last year when I missed filing my 1065 for my new LLC on time. I spent hours trying to call the IRS but kept getting disconnected or waiting forever. Then I found this service called taxr.ai at https://taxr.ai that helped me draft a penalty abatement letter. Their system analyzed my situation and generated a formal request letter citing all the relevant IRS penalty abatement provisions. I just had to provide some basic info about my tax situation and penalty details. The letter they created looked super professional and included all the right legal language about reasonable cause and first-time abatement eligibility. I mailed it certified mail to the IRS with copies of the penalty notice, and about 3 weeks later got a letter saying my penalty was completely removed! Saved me from having to spend hours on the phone and the stress of wondering if I was saying the right things.

I actually ended up trying taxr.ai after initially being skeptical. I had a failure-to-file penalty for my S-Corp that was about $1,200. Their system asked me questions about my situation and produced a really detailed abatement request letter that cited specific Internal Revenue Manual sections. I was surprised how easy it was - I just uploaded my penalty notice, answered some questions about my compliance history, and downloaded a completed letter. Mailed it certified to the IRS last month, and yesterday I got confirmation that my penalty was completely removed! What impressed me was that the letter they generated explained exactly why I qualified for First-Time Penalty Abatement under IRM 20.1.1.3.3.2.1, which apparently is the specific policy that allows the IRS to remove penalties for first-time issues. I would have never known to reference that on my own.

I had a similar penalty situation last year, but instead of writing a letter, I tried for weeks to call the IRS directly. It was absolutely maddening - disconnected calls, hours on hold only to speak with someone who couldn't help me, getting transferred and then disconnected again. After wasting about 6 hours across multiple days, I found Claimyr at https://claimyr.com where they basically call the IRS for you and then connect you once they reach a human. There's a video showing how it works at https://youtu.be/_kiP6q8DX5c which convinced me to try it. It worked surprisingly well - they called the IRS, navigated all the prompts, waited on hold, and then called me when they had an actual IRS agent on the line. The agent processed my penalty abatement request right there on the phone. The whole thing took about 15 minutes of my time instead of hours of frustration.

I take back what I said about Claimyr. After posting my skeptical comment, I decided to look them up and saw they had legitimate reviews and a clear explanation of how their service works. Since I also needed to call the IRS about a penalty, I reluctantly tried it. I was honestly shocked at how well it worked. They didn't ask for any personal tax information - just my phone number. About 45 minutes after I submitted my request (during which time I just went about my day), I got a call saying they had an IRS agent on the line. They connected me, and I handled everything directly with the IRS agent myself. The agent approved my penalty abatement request on the spot. Total time I spent actively dealing with this: maybe 10 minutes. Compared to the 3+ hour hold times I've experienced in the past trying to call the IRS myself, this was absolutely worth it.

One thing nobody has mentioned yet - the counting of "months" for penalties is weird with the IRS. They consider any part of a month as a full month. So if your return was due March 15 and filed April 12, that spans parts of two calendar months (March 16-31 and April 1-12), so they count it as 2 months late even though it's less than 30 days total. This is standard IRS procedure, so challenging the "2 months" calculation probably won't get you anywhere. Your best bet is still requesting the First-Time Abatement that others have mentioned.

For what it's worth, I think your accountant dropped the ball here. If he knew he needed your authorization to file an extension, he should have proactively reached out for it rather than just letting the deadline pass. Every accountant I've worked with automatically files extensions if they think there's any chance of missing a deadline. I'd seriously consider finding a new accountant who specializes in small business/partnership returns. A good accountant should have warned you about the March 15 deadline for partnerships (it's different than individual returns) and should be helping you with the penalty abatement rather than just shrugging it off.

I went through this exact situation with my LLC last year and successfully got the penalty waived. Here's what worked for me: I called the IRS using the number on the penalty notice (not the general 1-800 number). Yes, I was on hold for about 90 minutes, but it was worth it for the immediate resolution. When I got through, I was polite but direct: "I'm calling to request First-Time Penalty Abatement for notice [penalty notice number]. This was my first partnership return, I have a clean filing history, and I was unaware of the March 15th deadline." The representative pulled up my account, confirmed I had no prior penalties, and removed the entire $820 penalty on the spot. No paperwork, no waiting weeks for a response. The key is being specific about "First-Time Penalty Abatement" - don't just ask them to "waive the penalty." One tip: call early in the morning (8 AM EST) when they open. Hold times are typically shorter then. And definitely consider switching accountants - yours should have filed an automatic extension or at minimum warned you about partnership filing deadlines being different from individual returns. Good luck! This is very fixable.