dnscrypt-proxy/cloudflared for DNS over HTTPS

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Expected Behaviour:

Running the cloudflare ESNI test I expect to see secure DNS pass as DNS over HTTPS should be enabled.

Actual Behaviour:

DNSSEC and TLS1.3 pass but SNI and secure DNS tests fail. However, all the other tests I've run seem to show it working fine. When i disable the service I can't resolve anything, and every other test method I've found seems to work. I've tried with both cloudflared and dnscrypt-proxy. Currently I am using dnscrypt-proxy since cloudflared would return SERVFAIL for every
dig @127.0.0.1 -p 5053 google.com query while dnscrypt-proxy returned NOERROR.

Debug Token:

https://tricorder.pi-hole.net/rrguw54m9o

Some guidance would be much appreciated. There's a ton of information out there, much of which is out of date or for older versions. I've been loving pihole so far.

Is this a Pi-hole issue? Pi-hole simply forwards the DNS queries to the upstream servers, in your case cloudflared. If cloudflared is not working correctly, try contacting them.

I’m not sure exactly which is why I was asking :smiley:

But after some more investigating seems like you’re most likely right, just confused as to why both dnscrypt and cloudflared having similar problems in the setup.

Was just wondering if anyone else had similar issues with dns over https proxy servers and pihole

I still have issues with routes to Cloudflare 1.1.1.1:

pi@noads:~ $ host pi-hole.net 1.1.1.1
;; connection timed out; no servers could be reached

pi@noads:~ $ traceroute -n 1.1.1.1
traceroute to 1.1.1.1 (1.1.1.1), 30 hops max, 60 byte packets
 1  10.0.0.1  0.655 ms  0.572 ms  0.591 ms
 2  192.168.1.1  0.848 ms  0.775 ms  0.733 ms
 3  62.58.240.1  49.050 ms  48.599 ms  48.578 ms
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The second one 1.0.0.1 does work though:

pi@noads:~ $ host pi-hole.net 1.0.0.1
Using domain server:
Name: 1.0.0.1
Address: 1.0.0.1#53
Aliases:

pi-hole.net has address 206.189.252.21
[..]

pi@noads:~ $ traceroute -n 1.0.0.1
traceroute to 1.0.0.1 (1.0.0.1), 30 hops max, 60 byte packets
 1  10.0.0.1  0.653 ms  0.582 ms  0.743 ms
 2  192.168.1.1  0.852 ms  0.781 ms  0.747 ms
 3  62.58.240.1  16.591 ms  16.879 ms  16.557 ms
 4  212.53.25.201  16.448 ms  16.139 ms  35.353 ms
 5  212.53.25.193  16.271 ms  16.431 ms  16.469 ms
 6  212.151.190.0  16.866 ms  16.744 ms  16.549 ms
 7  130.244.82.55  19.369 ms  19.312 ms  19.018 ms
 8  212.151.176.245  19.415 ms  19.580 ms  19.318 ms
 9  * * *
10  1.0.0.1  16.872 ms  16.986 ms  16.700 ms

But this could be related to my ISP only.
Maybe still after effects of below one:

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