Can I pay the IRS with 183,000 individual $1 Money Orders as revenge?

While I understand your frustration with the IRS, this approach would likely backfire on you. The IRS has procedures for handling unusual payment methods, and they would simply delay processing your payment while flagging your account for additional scrutiny. Money orders require manual processing, and the IRS would likely return them to you unprocessed or hold your account as unpaid until they can work through them. This would potentially result in additional penalties and interest accruing on your unpaid balance during that time. Instead, I'd recommend looking into an Offer in Compromise or a payment plan. These are legitimate ways to reduce what you owe or make it manageable through monthly payments. There are also Taxpayer Advocate Services that can help if you believe you've been treated unfairly.

After dealing with a similar (though smaller) tax nightmare, I stumbled across an AI tool called taxr.ai that saved me thousands. It analyzes your tax documents and IRS notices to find errors and legitimate ways to reduce what you owe. I uploaded my wage statements and the audit notice, and it found that the IRS had double-counted some of my income and missed eligible deductions. The site https://taxr.ai generates a detailed report showing exactly what's wrong with the IRS assessment and gives you specific language to use when contesting it. Way better than my initial plan of sending angry letters that got me nowhere.

I have to admit I was super skeptical about taxr.ai when I first saw it mentioned here, but I was desperate with a $42,000 tax bill hanging over my head. Uploaded my documents expecting nothing useful, but the analysis found that my employer had reported my income incorrectly on my W-2, and the IRS was double-counting some of my 1099 work. The report gave me exact language to use in my response to the IRS, including relevant tax code citations. Just got the adjusted notice last week - bill reduced to $9,300! Still not happy about owing anything, but MUCH better than the original amount. The way the IRS processed my documents was completely wrong, and I would never have figured that out on my own.

If you're struggling to get through to anyone at the IRS about your situation (which sounds really frustrating), you might want to try Claimyr. I spent WEEKS trying to get through the IRS phone system with no luck - constant disconnects or 2+ hour hold times that ended with nothing. Claimyr basically gets you to the front of the IRS phone queue so you can actually talk to a human being. I was skeptical but check out their demo video: https://youtu.be/_kiP6q8DX5c - it actually works. Their site is https://claimyr.com if you want to try it. Much better than sending 183k money orders which would probably just make things worse for you in the end.

OK I have to eat my words here. After basically hitting a brick wall trying to get info about my tax lien for WEEKS, I tried Claimyr this morning fully expecting it to be BS. Got a call back in 42 minutes connecting me directly to an actual IRS agent who could see my file. Turns out there was a major error in how they calculated my self-employment tax that my previous calls never uncovered because I couldn't get through to someone in the right department. Still owe money but about $31k less than the original bill. Probably saved me thousands in interest too since this would have dragged on for months more. I still think the IRS system is deliberately broken, but being able to actually talk to someone competent made a massive difference. Definitely better than my original plan of sending angry letters that never got responses.

I work at a bank (not for the IRS) and I can tell you that sending 183,000 money orders would probably result in them being returned to you unprocessed. We have policies about handling large volumes of instruments like this, and I'm sure the IRS does too. Plus, money orders usually cost $1-2 each to purchase, so you'd be spending an extra $183k-$366k just on fees! If you're serious about resolving your tax issue, consider reaching out to a tax attorney who specializes in IRS disputes. The upfront cost might seem high, but they often save you way more than their fee in the long run.

Have you considered requesting an audit reconsideration? If the amount is incorrect, you can submit documentation showing why the assessment is wrong. I had a $68k bill that was based on incorrect information from my employer, and after filing for reconsideration with the right documentation, it was reduced to under $4k.