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Selfhosted
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There’s two ways around the symptoms you’re trying to treat:
Probably worth calling out that although 1 feels like there’s more hops (and there absolutely are), with any decent internet, you’re probably not going to feel it. This is because the edge server is probably situated very close to your ISP (that’s how they make sure everything responds quickly) so your over all round trip should only be affected by a negligible amount of time that you most likely won’t notice.
Barring any Traefik tricks that allows me to accomplish what I'm after, I was thinking of going with your "third" option of just letting it use Cloudflare for everything but, I had to check with the experts first before just doing it.
I have some apps that complain or, in one case, flat out doesn't work if the cert is invalid. I've been working around it (sort of) but it would be nice to have it set up "correctly" for once. If routing all traffic through Cloudflare is the answer, so be it ¯_(ツ)_/¯