The mystery of the missing emails

I guess that’s my point - the emails aren’t going direct to Google. If you have a forward at Hover, the emails have to be received by Hover’s mail server, get packaged back up as outgoing messages, and then sent to Google.

Absolutely - not unique to Google.

The issue here is that the forward actively exacerbates the problem. You may already know this @WayneG, but I’m guessing most people don’t. Here’s the process:

  • Hover gets an SMTP request asking it to accept email for somebody@somedomain.com
  • Hover makes a determination whether to receive the email, based on the sending server’s IP, DKIM, DMARC, etc.
  • Once it receives the email, it consults its rules about delivery. In this case it sees that it’s supposed to forward to somebody@gmail.com
  • Hover packages up the email, and tries to deliver it to somebody@gmail.com
  • Gmail sees a request from Hover for it to accept an email to somebody@gmail.com
  • Gmail makes a determination whether to receive the email, based on Hover’s IP reputation, DKIM, DMARC, etc.

And it’s that last step that’s really the issue. Leaving aside DKIM/DMARC/SPF/etc., if Hover is configured to forward all mail indiscriminately, that means Hover is forwarding a bunch of spam. Which means Gmail sees Hover’s mail server as a source of spam. Which can cause Hover’s reputation to go down in Gmail’s eyes. Which means good mail from Hover is less likely to get through.

I run a mail server, and I’ve seen this happen. Customers never understand it, but it’s a huge problem.

In an ideal world, Hover would be doing spam filtering before forwarding. But since that’s been completely disabled:

OP’s world is far from ideal - and could actively be making the problem worse.

If the email isn’t time-sensitive (i.e. it’s okay for it to show up 30-45 minutes after it arrives at Hover), gating it to Gmail via Gmail’s POP3 integration is a far more reliable delivery method.

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