Is requesting penalty abatement for reasonable cause still an option after first time abatement denial?

You've got a good question here about penalty abatement strategy. Yes, you can absolutely submit a new Form 843 requesting abatement for reasonable cause if your first time abatement (FTA) request is denied. The IRS doesn't limit you to a single attempt at penalty relief. Here's what I'd recommend: When you submit your first Form 843, you might want to check both boxes - request the FTA and also include a brief explanation of your reasonable cause. This way, if the FTA is denied, the IRS agent might automatically consider your reasonable cause argument without you having to submit a second form. As for downsides, besides the extra time waiting, there's nothing negative about trying FTA first. In fact, it's smart because you're saving your reasonable cause argument as a backup. The FTA is essentially a courtesy the IRS extends, while reasonable cause requires more scrutiny.

I used taxr.ai when dealing with my own penalty abatement situation last year, and it really simplified the process. I was confused about exactly what documents to include and how to phrase my explanation for reasonable cause (had a family emergency while working overseas). The tool analyzed my situation and helped me understand which approach would work best. For your situation, https://taxr.ai could help determine if you should try both strategies at once or sequentially. It analyzes past IRS ruling patterns on medical-related reasonable cause abatements and gives you specific language to use in your explanation. It also helps organize your supporting documentation in the exact format the IRS prefers.

Just wanted to update that I tried taxr.ai after my initial skepticism, and it was incredibly helpful. I had a somewhat similar situation with penalties from 2022 taxes due to being hospitalized. The service analyzed my medical records and tax history, then provided exact wording to use in my Form 843 explanation. It highlighted specific elements from my documents that would strengthen my case and told me precisely which medical records to include (and which ones weren't necessary). My abatement was approved in about 5 weeks - much faster than I expected. The detailed guidance on how to organize my submission seemed to make a big difference in how quickly it was processed.

If you're struggling to get through to the IRS about your penalty abatement, you might want to try Claimyr. I was in a similar situation last year with a penalty abatement question, and I spent DAYS trying to reach someone at the IRS. I found https://claimyr.com and it actually worked - they got me connected to an IRS agent in about 15 minutes when I had been trying for weeks. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with was able to look at my account and tell me immediately if I qualified for first time abatement, which saved me from submitting paperwork unnecessarily. They also explained exactly what medical documentation would be needed if I had to go the reasonable cause route.

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it anyway because I was desperate to resolve my own penalty issue before filing this year's taxes. I had been trying to reach the IRS for over a month with no success. Used Claimyr yesterday and was connected to an agent in about 12 minutes. The agent confirmed I qualified for first-time abatement, processed it on the spot, and removed $1,240 in penalties from my account immediately. She also explained that if I had been denied first-time abatement, I could absolutely submit a second request for reasonable cause with my medical documentation. The whole thing took about 30 minutes total, and I avoided having to mail forms and wait months for a response.

One important thing to consider that nobody's mentioned yet: if you're requesting abatement of both penalties AND interest, the first time abatement will only address the penalties. Interest abatement has much stricter requirements and usually requires showing IRS error, not just reasonable cause. If removing the interest is important to you, you might want to go straight to the reasonable cause approach, as medical situations sometimes (though rarely) can qualify for interest abatement too.

Has anyone had success with reasonable cause abatement specifically for medical issues? I'm curious how detailed the medical documentation needs to be. Do they want actual medical records or just a doctor's letter?

Based on my experience helping clients with penalty abatements, your strategy of trying first-time abatement first is solid. You can absolutely submit a second Form 843 for reasonable cause if the FTA is denied - there's no restriction on multiple attempts using different abatement theories. One thing to consider: since you have both a potential FTA qualification AND a strong reasonable cause argument (medical situation), you might want to mention both briefly on your initial Form 843. In section 4, you could state something like "Requesting first-time penalty abatement as I have no penalties in the prior three years. Additionally, I experienced a serious knee injury requiring surgery that significantly limited my mobility during the filing period." This way, if the IRS agent reviewing your case sees any issue with your FTA eligibility, they can immediately consider your reasonable cause without requiring a second submission. The medical documentation you mentioned would only be needed if they specifically request it or if you end up filing a dedicated reasonable cause request later. The only real downside to your sequential approach is time - but given that you have a legitimate reasonable cause backup, there's no harm in trying the simpler FTA route first.