On Wed, Mar 12, 2025 at 09:51:36AM +0100, BetaRays wrote:
> I had filter dkimsign chain { dkimsign_rsa1024, dkimsign_ed25519 } at
> first, which I replaced with filter dkimsign chain { dkimsign_ed25519, 
> dkimsign_rsa1024 }
> after trying filter dkimsign chain { dkimsign_rsa1024 } in case that
> changed something, but I’m not sure if I ever tried sending an email to
> gmail with that new configuration.
> 
> In any case, I did just now and it went through, so it seems that might
> have been the issue (or there is some random choice in the anti-spam
> mechanism).
> 
> Thank you for your time.

In case anyone is interested or finds this archive in the future: the
issue was most likely not linked to DKIM.

I recently applied this patch 
https://github.com/OpenSMTPD/OpenSMTPD/pull/1275/files
because the portable version would not use my given IPv6 address as a
source, and I have encountered the same issue with my IPv6 address,
while my IPv4 address is still accepted by gmail.

Maybe gmail blocks the first attempts at sending email for every IP
address: both have a reverse DNS entry pointing to the same domain and
should be valid with my SPF records, so I don’t have another
explanation.

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