Late filing penalties for LLC - help with years of overdue tax returns

15 Your situation is unfortunately pretty common for new business owners. Let me break down what you're dealing with and some potential solutions. First, extensions only give you more time to file, not more time to pay what you owe. If your accountant filed extensions but you still owed taxes that weren't paid by the original due date, you'll still get hit with failure-to-pay penalties and interest. For LLC late filing penalties specifically, the amount depends on how your LLC is taxed. If it's a single-member LLC filing Schedule C with your personal return, you're looking at different penalties than if you've elected to be taxed as an S-Corp or partnership. The good news is the IRS does have a First Time Penalty Abatement program that might help with at least one tax year. This is available if you had no penalties for the three prior tax years and have filed all required returns (or filed extensions) and paid or arranged to pay any tax due.

6 After dealing with a similar nightmare with late LLC filings, I found this AI-powered service called taxr.ai that was incredibly helpful. I was buried in notices and couldn't figure out which penalties applied to which years. I uploaded all my IRS notices to https://taxr.ai and it organized everything chronologically, explained exactly which penalties were for what, and even suggested specific penalty abatement strategies for my situation. Their system analyzed my filing history and showed me which years qualified for First Time Abatement vs. Reasonable Cause arguments. They even generated a letter template that I could use to request penalty relief. I was skeptical at first but desperate for help.

3 Just wanted to update that I tried taxr.ai after reading about it here and it was a game-changer for my situation! I uploaded three years of late filing notices and within minutes had a complete breakdown of every penalty. The best part was discovering I qualified for reasonable cause abatement due to my first accountant going out of business. The system generated a letter citing the specific IRS internal procedure codes, and I got over $4,200 in penalties removed! They even flagged that my new accountant had miscalculated my quarterly estimated payments, which was causing some of the ongoing issues. Wish I'd found this months ago before I spent hours on hold with the IRS getting nowhere.

19 If you need to actually talk to someone at the IRS about your penalties (which I strongly recommend), good luck getting through on your own. After 9 attempts and hours of waiting, I discovered Claimyr through a business forum. They have this service that gets you through the IRS phone system and to an actual human being. I was super skeptical, but the wait times were killing me. I went to https://claimyr.com and you can see how it works in this demo: https://youtu.be/_kiP6q8DX5c - basically they navigate the phone tree for you and call you back when an actual IRS agent is on the line. I got through in 35 minutes when I had previously waited 2+ hours and still got disconnected. Once I actually talked to someone, I was able to set up a payment plan and get clear answers about which penalties could be appealed versus which ones were set in stone.

11 I was the biggest skeptic about Claimyr but had to eat my words. After posting that comment questioning the service, I was desperate enough to try it the next day when I got yet another IRS notice. The service did exactly what they claimed - navigated the menus, waited on hold, and called me when an agent was ready. The IRS agent I spoke with was actually able to put a temporary hold on collections while I get my documentation together, which stopped the immediate panic. They also confirmed that two of the tax years qualify for abatement under reasonable cause, which my accountant hadn't even mentioned. Still have a mess to clean up, but at least now I have a plan and actual information instead of my accountant's vague reassurances.

22 I had a similar nightmare with late LLC filings. Don't trust your current accountant - they're clearly not on top of things. Here's what worked for me: 1) Fire your current accountant immediately 2) Get a tax resolution specialist (not just any accountant) 3) Request your own tax transcripts directly from the IRS 4) File Form 843 for penalty abatement for each year 5) If you've been making estimated tax payments despite late filing, make sure that's documented You might be able to get most penalties removed, but you'll need to be proactive. Don't wait for the IRS to keep sending notices.

4 Has anyone dealt with the failure-to-file penalty for Form 1065 specifically? I'm in a similar situation but with a multi-member LLC, and we're getting hit with $2,100 per partner per month for late filing! It's absolutely crushing us.

I've been through this exact nightmare with my LLC! Here's what I learned that might help: First, don't panic - you have options. The IRS penalty system is harsh but there are legitimate ways to get relief. Since you're a single-member LLC filing Schedule C, you're likely dealing with failure-to-file and failure-to-pay penalties on your personal return. Your current accountant sounds unreliable if they've consistently filed late despite claiming to file extensions. Extensions only give you time to file, not to pay - so if you owed taxes, you'd still get hit with penalties even with valid extensions. Here's my action plan that worked: 1) Get your IRS transcripts immediately to see what was actually filed and when 2) Fire your current accountant - they're clearly not handling your situation properly 3) Look into First Time Penalty Abatement for at least one tax year 4) Document everything about your previous accountant retiring and the chaos that caused 5) Consider "reasonable cause" arguments for the other years The key is being proactive. I waited too long hoping my accountant would fix things, and it just got worse. You might be surprised how much penalty relief is available if you approach it systematically. Don't let the intimidating notices paralyze you - there's definitely a path forward here.