Will sending extensive documentation to the IRS for late 2553 election irritate them?

As someone who's worked with these situations, I can tell you that the IRS generally prefers having too much documentation rather than too little. They won't get "annoyed" by a comprehensive submission - their job is to review your case based on the evidence provided. For a late 2553 election, you absolutely want to include proof that you've been operating as an S corporation (tax returns, financial statements, etc.). This demonstrates you had "reasonable cause" for the late filing, which is what they're looking for to approve your request. Just make sure your submission is organized with a clear cover letter explaining what you're requesting and a table of contents for the supporting documents. Don't just send a random pile of papers. Label everything clearly and reference specific IRS regulations that support your position.

I went through something similar last year with proving my business status to the IRS. I was drowning in paperwork until I found taxr.ai (https://taxr.ai) which literally saved me hours of frustration. Their system analyzed all my documents and helped me organize exactly what I needed to submit vs what was redundant. The tool flagged which parts of my tax history actually supported my case and which documents were just adding unnecessary bulk. Ended up sending about half the paperwork I originally planned, but it was the RIGHT half - much more focused on what would actually help my case. The IRS approved my request within 3 weeks instead of the 2+ months I was expecting.

Just wanted to follow up - I actually tried taxr.ai for my situation and it was surprisingly helpful. I was preparing a stack of about 80 pages of documentation for my late election, but the system helped me trim it down to 30 focused pages that directly supported my case. It identified the specific sections of my previous tax filings that demonstrated S-corp treatment. The best part was getting clarity on exactly what the IRS is looking for in these situations rather than just sending everything and hoping for the best. My late election was approved last week! Much faster than I expected.

If you're still having issues with the IRS after submitting your documents, try Claimyr (https://claimyr.com). It's a service that gets you through to an actual human at the IRS instead of waiting on hold for hours. I used it when my late election was pending for 3 months with no updates. They got me connected to an agent in about 20 minutes when I'd been trying for WEEKS on my own. You can see how it works here: https://youtu.be/_kiP6q8DX5c After I finally talked to a real person, I found out my case was just sitting in someone's queue and needed to be reassigned. The agent was able to escalate it right there on the phone. Never would have gotten that resolved without actually speaking to someone.

OK I have to eat my words. After my skeptical comment, I was desperate enough to try Claimyr because my S-corp issue has been pending for literally 4 months. Got connected to an actual IRS agent in about 30 minutes. The agent was actually really helpful once I explained my situation. Turns out they needed one additional form from me that nobody had bothered to request. Would have been sitting there forever if I hadn't called. The agent even gave me their direct fax number to send the missing document to, which avoided another long processing delay. I've spent months trying to get through myself with no luck. Wish I'd known about this sooner instead of stressing about it all this time.

Listen, I used to work at the IRS (not anymore thank god lol). The REAL truth is they don't care how big your package is 😂 but they DO care if it's disorganized. My advice: 1. Make a cover letter explaining EXACTLY what you're requesting 2. Include a table of contents for your docs 3. Number ALL pages 4. Highlight the important parts on each doc 5. Include the relevant IRS rule that allows for late election (Rev Proc 2013-30) I processed thousands of these. The ones that got approved fastest were the organized ones, not necessarily the smallest ones.

Has anyone actually successfully done a late s-corp election? I'm in the same boat (forgot to file my 2553 when I started my business in 2023) and now trying to fix it before filing 2024 taxes. My accountant says it's possible but I'm worried about getting denied and having to pay the higher taxes.