iPhone > Safari webkit > WireGuard tunnel home network > PiHole DNS (Quad9 upstream) > WireGuard tunnel ProtonVPN endpoint
That is the flow of my current network.
Edit: I ran curl from my server
┌─[user@debian] - [~/compose] - [Thu Aug 13, 12:26]
└─[$]> curl -v https://angieguardian.org/
* Host angieguardian.org:443 was resolved.
* IPv6: (none)
* IPv4: 77.61.56.117
* Trying 77.61.56.117:443...
* ALPN: curl offers h2,http/1.1
* TLSv1.3 (OUT), TLS handshake, Client hello (1):
* CAfile: /etc/ssl/certs/ca-certificates.crt
* CApath: /etc/ssl/certs
* Recv failure: Connection reset by peer
* TLS connect error: error:00000000:lib(0)::reason(0)
* OpenSSL SSL_connect: Connection reset by peer in connection to angieguardian.org:443
* closing connection #0
curl: (35) Recv failure: Connection reset by peer
┌─[user@debian] - [~/compose] - [Thu Aug 13, 12:27]
└─[$]> curl -v angieguardian.org
* Host angieguardian.org:80 was resolved.
* IPv6: (none)
* IPv4: 77.61.56.117
* Trying 77.61.56.117:80...
* Connected to angieguardian.org (77.61.56.117) port 80
* using HTTP/1.x
> GET / HTTP/1.1
> Host: angieguardian.org
> User-Agent: curl/8.14.1
> Accept: */*
>
* Request completely sent off
* Recv failure: Connection reset by peer
* closing connection #0
curl: (56) Recv failure: Connection reset by peer
Can confirm my PiHole is resolving the requests and forwarding them to Quad9.

