I had a bit of email drama this week; Gmail started classifying half of my incoming legitimate email as spam. I got some great help from Gmail support who explained the problem and taught me how to properly forward email.

In detail, what happened… I get all my email to nelson@monkey.org, which I forward via procmail and SMTP to my gmail account. For some reason monkey.org recently got branded a possibly spammy domain. Because of my forwarding Gmail was under the impression that all my email was coming from monkey.org, so a bunch of it started getting marked as spam. The Gmail UI is a bit buggy in this circumstance; it was misidentifying which domain was the problem, telling me “we’ve found that lots of messages from gmail.com are spam” and the like when the real problem was monkey.org.

I fixed the problem by forwarding my mail properly. Gmail doesn’t just use the From: email header to identify the sender, it also uses the (normally invisible) From⎵ SMTP envelope. And because I misconfigured procmail, that header was always being set to nelson@monkey.org (since I was sending the mail). You can spoof the envelope too via -f, you just have to set it up that way. (Which makes me wonder why the spam filter pays any attention to it.)

It's a subtle problem; I only noticed it after several years. If you use procmail to forward to Gmail, you may want to look into your configuration. I believe most more ordinary forwarding mechanisms don’t have the envelope problem. Procmail is weird in that it’s generating new emails, not forwarding existing ones.