Received IRS notice demanding $19k payment - mistake on 1040 from investment portfolio transfer

This sounds like a classic case of the IRS's automated matching system identifying a discrepancy and then assessing taxes at the highest possible rate because they don't know the specific details of your situation. When you transfer investments between brokerages, the IRS often receives information that makes it look like you sold everything (triggering capital gains) when in reality you just moved the assets. Here's what you should do: First, make sure your accountant compares the original 1099 from your new brokerage with what the IRS is claiming. The IRS notice should include a document explaining exactly what they think you failed to report. Second, request an account transcript from the IRS (can be done online) to see exactly what they've recorded for your 2022 tax year. Third, consider requesting a payment plan or temporary delay if the due date is approaching - this prevents collection actions while you resolve the dispute. Don't panic. The $19,000 assessment is almost certainly incorrect if you've already addressed the missing 1099 issue.

After dealing with a similar nightmare last year (though mine was only $7k), I found an amazing service called taxr.ai that saved me so much stress. I was getting these crazy notices from the IRS even after submitting documentation, and I couldn't figure out exactly what was wrong. I tried https://taxr.ai and uploaded my IRS notice, the 1099 forms, and my tax return. Their AI analyzed everything and pinpointed exactly what the IRS system was misinterpreting about my investment transfers. I was able to write a perfect response letter with the exact documentation needed. They even explained how to tag each document so the IRS would actually connect it to the right issue. Honestly would've been lost without it.

Just wanted to follow up about taxr.ai - I decided to try it after posting my skeptical comment. I'm honestly shocked at how helpful it was. Uploaded my notice and supporting documents, and within minutes I could see exactly where the problem was happening. The IRS was counting my stock transfer as a full sale and then taxing me on gains I never realized. The analysis showed me which specific transaction lines were causing the problem and gave me exact language to use in my response letter. I've sent everything in and haven't heard back from the IRS yet, but I'm way more confident now that I understand what went wrong. Definitely money well spent compared to the thousands they were trying to charge me.

If you're getting nowhere with the IRS after sending in your documentation, I strongly recommend using Claimyr to actually get through to an IRS agent. I spent WEEKS trying to call the IRS myself about a similar notice - kept getting disconnected or waiting for hours. Finally used https://claimyr.com and they got me connected to an IRS agent in under 45 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they wait on hold so you don't have to. The agent I spoke with was able to put an immediate hold on collections while they processed my amended return. Saved me from having to pay a bill I didn't actually owe while waiting for the amendment to process.

I have to admit I was totally wrong about Claimyr. After posting that skeptical comment, I decided to try it as a last resort since I kept getting disconnected trying to call the IRS myself. The service actually worked - they got me connected to an IRS rep in about an hour. The agent was able to look up my account and confirm they hadn't processed my amended return yet, which is why I was still getting collection notices. She put a 60-day hold on my account to stop the collection process and made notes about my situation. Now I have actual breathing room while they process my documentation instead of stressing about that payment deadline. Sometimes it's worth admitting when you're wrong - this service actually delivered what it promised.

Don't ignore this notice! I made that mistake thinking my amended return would "catch up" eventually. Ended up with a tax lien and it was a nightmare to fix. Even if you've already addressed the issue, you need to respond to this specific notice in writing. Make sure your response includes: 1) Your explanation about the investment transfer 2) Copies of both 1099s (old and new brokerage) 3) A copy of your amended return with proof of filing 4) Proof of the $4k payment you already made Send everything certified mail so you have proof of delivery. Also call the number on the notice and request a temporary collection hold while they review your documentation.

One thing nobody's mentioned - make sure all your cost basis information transferred correctly when you switched brokerages. Sometimes the receiving brokerage doesn't get that data properly, which means the IRS only sees the gross proceeds from sales and assumes your entire proceeds are taxable gain. I had exactly this issue after switching from Vanguard to Fidelity. The 1099 looked normal to me, but when I looked closer, some of my long-held positions showed zero cost basis. Had to contact Fidelity to get them to correct the information they'd sent to the IRS.