dnsmasq not working on Mac OS Sierra I'm running dnsmasq on a 2016 MBP running Mac OS Sierra (10.12.1) but I'm unable to ping any .dev addresses despite having what I believe is the proper config. Running dig does return sane output.

/usr/local/etc/dnsmasq.conf

resolv-file=/usr/local/etc/resolv-dnsmasq.conf
address=/.dev/127.0.0.1


/etc/resolver/dev

nameserver 127.0.0.1


/usr/local/etc/resolv-dnsmasq.conf

nameserver 8.8.8.8
nameserver 8.8.4.4


My DNS server list in System Preferences has only one entry pointing to 127.0.0.1.

When I run dig on a .dev address I get the following output:

; &lt;&lt;&gt;&gt; DiG 9.11.0-P1 &lt;&lt;&gt;&gt; test.dev
;; global options: +cmd
;; Got answer:
;; -&gt;&gt;HEADER&lt;&lt;- opcode: QUERY, status: NOERROR, id: 36126
;; flags: qr aa rd ra ad; QUERY: 1, ANSWER: 1, AUTHORITY: 0, ADDITIONAL: 0

;; QUESTION SECTION:
;test.dev.          IN  A

;; ANSWER SECTION:
test.dev.       0   IN  A   127.0.0.1

;; Query time: 0 msec
;; SERVER: 127.0.0.1#53(127.0.0.1)
;; WHEN: Mon Dec 19 23:13:20 PST 2016
;; MSG SIZE  rcvd: 42


I'm able to load external sites like google.com perfectly but if I try accessing a local web server or even pinging a .dev address it fails.

Help would be appreciated!
Your dnsmasq daemon isn't properly configured.

Your external resolver is working: all queries to non-dev hosts/domains are forwarded to 3rd-party DNS servers with the resolv-file=/usr/local/etc/resolv-dnsmasq.conf line - in your case the configured file contains two public Google DNS servers.

Your internal resolver doesn't resolve internal names though.

The line address=/.dev/127.0.0.1 or better address=/dev/127.0.0.1 will redirect any *.dev query to the host 127.0.0.1. An internal resolver is not needed then and the internal name server defined in /etc/resolver/dev is useless.

Compare this with the example in the dnsmasq.conf file:

# Add domains which you want to force to an IP address here.
# The example below send any host in double-click.net to a local
# web-server.
#address=/double-click.net/127.0.0.1


Any query for *.double-click.net will be redirected to 127.0.0.1 and to an arbitrary website served at localhost.

I strongly recommend to define a hosts.config file and enter/define all necessary hosts there:

Add a line addn-hosts=/usr/local/etc/hosts/hosts.conf in dnsmasq.conf. Then add a folder with sudo mkdir /usr/local/etc/hosts and create a file hosts.conf 

sudo nano /usr/local/etc/hosts/hosts.conf


with the following content:

127.0.0.1   localhost
127.0.0.1   test.dev
127.0.0.1   test2.dev
...


After saving the file reload your dnsmasq daemon.

If you want to use different IPs for your host names e.g.:

127.0.0.1   localhost
127.0.0.2   test.dev
127.0.0.3   test2.dev
...


you'd have to add additional IPs with:

sudo ifconfig lo0 alias 127.0.0.2 up
sudo ifconfig lo0 alias 127.0.0.3 up
...