this post was submitted on 12 Aug 2026
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Privacy
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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
Can confirm my PiHole is resolving the requests and forwarding them to Quad9.
wow. uh okey, quite a complex setup. But in this specific case it's not even reaching Angie Guardian.. Let alone Angie/Nginx.. It fails clearly at TLS handshaking and the non-TLS is unclear why it fails.
Here is an example if what I would have expected using curl via httpS:
But your non SSL is maybe even more interesting.. since that is also failing (port 80 has NO angie guardian protection btw), here I would expected the following:
TDLR; clearly something else goes wrong with this setup.