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Hi! @styris-ame

Honestly, I didn't consider this kind of edge case. Currently, https_redirection works at the app level (per server_name), not per individual reverse_proxy target. In your case, a possible work around is to disable https_redirection for hosting .well-known with plaintext http.

I think it might be better to implement a new upstream option like disable_https_redirection in future.

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