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As of July 11, I'm getting this from civimail messages, mostly to @gmail.com addresses. The same install has been successfully sending out to the same address list for a long time.

550-5.7.1 [209.15.213.100] Messages missing a valid messageId header are not 550 5.7.1 accepted.

I've turned on the checkbox that generates it, so perhaps problem solved, but is this a policy change from gmail?

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    Perhaps most smtp services are already adding this? This one is going out directly from the server via postfix, so maybe there's a setting in there? I'm surprised this hasn't been flagged as a bigger deal.
    – Alan Dixon
    Commented Jul 12, 2022 at 18:00
  • Here's an indication that something might have changed at google mail servers: blog.mxtoolbox.com/2022/06/09/…
    – Alan Dixon
    Commented Jul 18, 2022 at 16:17

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I'm getting a number of other flags from other systems that gmail's deliverability rules have changed. Although DKIM still isn't required, it appears that there's been an update to google's algorithm that decides whether email is spam or not, and it's harder to cross than it used to be.

Bottom line: for civimail deliverability, you probably need at least SPF, the messageId, and a "cleanish" ip reputation, and I suspect that DKIM on the from address will help.

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  • Also don't send spam (grin).
    – Demerit
    Commented Jul 26, 2022 at 21:22
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    Well, in fact, you might think so, but I'm not convinced. It depends on your definition of spam, and ultimately, the only one that matters for the purpose of deliverability is that of the mail provider, and with the proliferation of "AI", that definition is harder to figure out, and subject to all kinds of weird manipulation by bad actors.
    – Alan Dixon
    Commented Aug 10, 2022 at 13:33
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    Also, there are multiple gates for deliverability - and not all of them result in a bounce. So it's really a dark art.
    – Alan Dixon
    Commented Aug 10, 2022 at 13:34

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