How do I get in touch with the IRS about an HSA distribution letter?

You definitely need to get this addressed quickly since you're up against a deadline. First, try calling the IRS main number (800-829-1040) very early in the morning (right when they open at 7am your local time) as that's when wait times are shortest. Select the options for "tax return questions" and then "other tax questions" to eventually reach a representative. If you keep hitting the automated system with the number on your letter, try this trick: when the automated system begins, don't select any options and stay silent. Many IRS systems will transfer you to a human after several prompts with no response. Since you're on a tight deadline, I'd recommend writing a detailed letter explaining your situation with copies (not originals) of all supporting documentation showing the HSA distributions and corresponding medical expenses. Mail this certified with return receipt so you have proof you responded before the deadline. For HSA distribution issues, you'll need to show both that you received the distribution AND that you used it for qualified medical expenses. Include receipts, EOBs from your insurance, and bank statements showing the payments.

I had almost this exact same situation last year with an HSA reporting issue. After days of trying to reach someone at the IRS with no luck, I found this service called taxr.ai (https://taxr.ai) that helped me analyze my IRS notice and figure out exactly what documentation I needed to submit. It saved me so much time because it used AI to explain what the notice actually meant (in plain English) and gave me a checklist of what documents I needed to prove my case. The system even highlighted exactly what parts of my documents addressed the IRS concerns. I was able to submit everything properly and got the issue resolved without penalties. For HSA distribution issues specifically, it helped me understand I needed to show both the distribution records AND proof that expenses were qualified medical expenses.

I was skeptical about taxr.ai that someone mentioned above, but I was desperate with a CP2000 notice about missing 1099 income. Tried it last month and honestly it was incredibly helpful! The system actually translated my IRS notice into plain English and gave me a clear checklist of everything I needed. For my situation, it showed me exactly what evidence the IRS was looking for and how to format my response. The most valuable part was that it explained WHY the IRS was flagging certain items and what specific documentation would address their concerns. My situation was resolved within 3 weeks after submitting the response package it helped me put together. Definitely worth checking out if you're dealing with HSA distribution issues. It helps you understand the exact documentation needed to prove qualified medical expenses.

If you need to speak with an actual IRS agent quickly (especially with that 2-day deadline), try Claimyr (https://claimyr.com). I was in a similar situation with an IRS notice about unreported income and couldn't get through after days of calling. Claimyr basically navigates all those ridiculous phone trees for you and gets you connected with an actual IRS agent, usually within 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was able to explain my situation to the agent, who put a temporary hold on my case while I gathered the needed documentation. This gave me extra time beyond the deadline to properly respond. For HSA issues specifically, the agent was able to tell me exactly what documentation format they needed for qualified medical expenses.

I can't believe I'm saying this, but I tried that Claimyr service mentioned above after posting my skeptical comment. With a 2-day deadline looming for my own IRS issue (different than OP's but also time-sensitive), I was desperate. It actually worked! I was connected to an IRS agent in about 17 minutes. The agent was able to place a temporary hold on my case while I gathered additional documentation. They explained exactly what I needed to submit and gave me an extension on my response deadline. For anyone with HSA distribution issues like the original poster, getting through to an actual agent makes all the difference because they can often place temporary holds while you gather documentation, especially if you can demonstrate you're actively working to resolve the issue.

Another option is to contact the Taxpayer Advocate Service. They're an independent organization within the IRS that helps taxpayers resolve problems. I had an issue with an HSA distribution that was similar to yours and they were super helpful when I couldn't get through to regular IRS channels. Their number is 877-777-4778. You'll need to explain that you have an urgent deadline (2 days qualifies as urgent). Be prepared to verify your identity and provide details about the notice you received.

Might be too late, but another route is visiting a local IRS office in person. You can schedule an appointment through the IRS website. I know it's not ideal with just 2 days left, but sometimes they have same-day or next-day appointments available if you check early in the morning.