Encryption

General
1

Will Pi-Hole ever natively support DNS encryption built in rather than having to install cloudflared?

2

There have been several feature requests.

3

It depends on if it will get implemented in dnsmasq. If this happens, it'll be added to Pi-hole for sure, too.

There are many arguments against encrypting to a single upstream provider and instead run your own recursive resolver. See the linked guide for further details.

4

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