macOS DoH! (DNS over HTTPS) using cloudflared

Install.txt

1) Install cloudflared using homebrew:

brew install cloudflare/cloudflare/cloudflared

2) Create /usr/local/etc/cloudflared/config.yaml, with the following content

proxy-dns: true
proxy-dns-upstream:
  - https://1.1.1.1/dns-query
  - https://1.0.0.1/dns-query

3) Activate cloudflared as a service

sudo cloudflared service install

4) Test

dig +short @127.0.0.1 github.com AA

5) If OK, change DNS on your mac to 127.0.0.1 (System Preferences->Network->Advanced->DNS)

cloudflared is documented at https://developers.cloudflare.com/1.1.1.1/dns-over-https/cloudflared-proxy/

If DNS resolving stop working, restart the service:

sudo cloudflared service uninstall
sudo cloudflared service install

Got problem Cannot determine default origin certificate path. No file cert.pem in [~/.cloudflared ~/.cloudflare-warp ~/cloudflare-warp /usr/local/etc/cloudflared /etc/cloudflared]
Solution: cloudflare/cloudflared#68

Works perfectly. Thank you.

However, when connecting via a VPN, the following issue occurs:

DNS server address 127.0.0.1 is a private address but is not being routed through the VPN.

For some reason, when a private address is used, Tunnelblick/OpenVPN is unable to override the default DNS with its own configuration as it is usually able to do.

Note that everything is still working correctly and neither my IP address nor DNS are leaking in a way that should compromise my privacy. Although, even if I decide to trust Cloudflare, I think I would prefer to use my VPN service's DNS server when I'm connected through it.

Anyone else run into this?

However, when connecting via a VPN, the following issue occurs:

DNS server address 127.0.0.1 is a private address but is not being routed through the VPN.

For some reason, when a private address is used, Tunnelblick/OpenVPN is unable to override the default DNS with its own configuration as it is usually able to do.

Anyone else run into this?

@fAS6NWnn7xA429U2, you have to do the following to make your VPN connection change DNS server:

1. First you have to add a line to your OpenVPN configuration file for each DNS server: "dhcp-option DNS address"
   Example:
   dhcp-option DNS 8.8.8.8
dhcp-option DNS 8.8.4.4

2. Then you have to make sure that "Set nameserver" in Tunnelblick's settings for the configuration is specified.

3. Lastly, you have to check "Allow changes to manually-set network settings" in "Advanced" for the configuration.

There you go 😃

@V33m — In that case, all I really needed to do was step 3. Thanks!

How do you personally feel about it? Would you rather keep 1.1.1.1 for normal internet activities and then switch it up for VPN use, or just go with 1.1.1.1 for everything to take advantage of its performance?

It's difficult to say the policies Cloudfare are going with. They have an agreement with Mozilla where they limit the logged data and data retention for Firefox users which enable DOH and are using DNS https://cloudflare-dns.com/dns-query. I don't think the limited logging policy is the case for DNS 1.1.1.1 / 1.0.0.1...

I advice you to setup different DOH servers for different cases/activities. Here is a list of some possible DOH servers: https://github.com/curl/curl/wiki/DNS-over-HTTPS

;; connection timed out; no servers could be reached

When I use dig +short @127.0.0.1 github.com AA

New Issue: Tunnelblick will only update the WiFi DNS, not the Ethernet DNS.

I've set the priority to Ethernet-first in the Mac settings, turned off WiFi, and even set it to inactive, but Tunnelblick will not switch to Ethernet.

Is there a way to alter Tunnelblick's network priority or more ideally, have it interact with Ethernet only?

Just a new open doh&dot service:

dns.containpi.com

https://apps.apple.com/in/app/privatedns/id1547063327 for iOS/iPadOS

Currently working on macOS app. :)

Works for me with config like:

resolver:
  enabled: true
  port: 53
  address: 127.0.0.1
  upstreams:
    - https://1.1.1.1/dns-query
    - https://1.0.0.1/dns-query

Have a typo.

/usr/local/etc/cloudflared/config.yml is the correct file. Drop the a.

Should be:

logDirectory: /var/log/cloudflared

proxy-dns: true
proxy-dns-upstream:
  - https://1.1.1.1/dns-query
  - https://1.0.0.1/dns-queryy≈