Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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I had a similar problem when using nginx proxy manager. In the end I just gave up and directly used cloudflare tunnels+cloudflare ssl
I think I've found the problem:
It seems my issue is pihole being unable to block/modify dns requests for HTTPS records, which don't match the LAN IPs pihole handed out in A/AAAA records.
I've disabled cloudflare proxying so they don't have HTTPS records to serve, but I'll have to replace pihole with a better lan DNS solution if I want to turn that back on.