I've looked into ARC which looks promising, but ARC is still experimental according to the wiki page so it's not really an option in my situation. The case is that addess a...@gmail.com sends a message to add...@somewhere.tld which has a forward to address b...@gmail.com. So it's not that the message is blocked because it would loop back to its sender. It looks like these messages mainly get lost (sometimes blocked) because the Google mailserver doesn't like a message originating from the gmail.com domain to come from a third party server, even if the DKIM signature of the original message is intact.

Op 17-05-2023 om 16:06 schreef Al Iverson via mailop:
Try rewriting the message ID. I think Gmail is believing the message
to be a duplicate and in some cases it will silently eat duplicates.

I have a forwarding feature for my own domains that in addition to
using SRS and re-signing DKIM with my domain, it rewrites the message
ID.

Good point about ARC; I don't have proof that it would fix things but
it would potentially be something to try.

Cheers,
Al

On Wed, May 17, 2023 at 4:23 AM Taavi Eomäe via mailop
<mailop@mailop.org> wrote:
Do those forwarded letters without SRS have intact DKIM?

A second thing you can try is ARC (without the SRS), I've gotten the
impression that Gmail "likes" original letters (and ARC) more than it
likes any kind of mangling, including SRS.

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