I've complained about this earlier and earlier still. Now, the mailing lists appear to work, but my own emails seem to get marked as spam by gmail.

I now installed DKIM, allowing it to sign also my sjl@iki.fi From-address. I tested the setup against Mail.app and a 3rd-party DKIM verifier, which accepted the email without problems. Gmail still marked my test message to spam.

It seems the problem is that I'm sending mail with sjl@iki.fi From: address from liskot.org domain. This is problematic, because in case I get tired of maintaining my own mail server, I want to be able to change to an external provider; precisely the reason for using an iki.fi address in the first place.

My first test email after enabling DKIM went to spam with Gmail indicating that "it was considered spam because similar emails have been considered spam before" (I'm not sure of the specific wording, reciting from memory). Nice feedback loop.

Apparently I need to monitor the situation even more closely, perhaps it is better now, perhaps not. If it does not improve, I really cannot continue sending as "sjl@iki.fi", as many people use Gmail as their email provider with a custom From-address (this works, of course, *inside* gmail just fine) , so I cannot choose to send with a different From-address to just those people.