I run my own mail server, and I am very concerned about its reputation and deliverability. I've run my own Linux server full time since at least 2017, obviously well before LLM's, but only recently put up a mail server. I don't usually run any agents on the server, such as Claude Code, ChatGPT Codex, or Grok Build, all of which I have subscriptions for but don't run on this server. Instead, I manually administer the server using ssh, while getting interactive help from ChatGPT in a chat window.

It was complicated to get security, DNSSEC, DKIM, DMARC right this way. I did it just under a year ago, around September 15, 2025.

I tried to follow and understand what I was doing, and keep good records on it. It was a complicated process, but everything was up and working at the end and I received email my server sent me. It felt good to be able use this simple script to send myself email:

     #!/usr/bin/env python3

     import smtplib
     from email.message import EmailMessage
     
     msg = EmailMessage()
     msg["From"] = "(user's from address)"
     msg["To"] = "(my gmail address)"
     msg["Subject"] = "(a test subject)"
     msg.set_content("(a test body)")

     with smtplib.SMTP("127.0.0.1", 25, timeout=30) as smtp:
         smtp.send_message(msg)
     
     print("Message submitted successfully to local Postfix.")

I understand that as my server's reputation grows, it becomes very powerful to be able to email anyone without any intermediary except potential spam filters. I am very careful about what I put on my server.

Nevertheless, I had a recent experience that was a little sad for me. I wanted to forward some mail to my gmail address automatically, and used ChatGPT Sol 5.6 on medium thinking time to help me with the administration to do this. (I find extra high and pro thinking times are excessively long.)

I was very disappointed with the results, which included a very badly written regex for authentication. I'll write up my experience in an experience report. It was a big disappointment for me.

The burden on administrating one's own email is already very large, and it is disappointing that we can't really rely on frontier models to help with it.