Pinging test.dev after Laravel Valet install returns "Unknown Host"

Question

Update: Don't use ".dev". When this was originally posted in 2016, it was fine. Now it's not. Start by changing your TLD to somethinge else like ".localhost" or whatever. (This change would not have fixed my issue, but it might fix yours if you're still using ".dev").

Problem: I've installed Laravel Valet and it all seems to be working except when I ping test.dev (which just contains an index.htm file and is located in ~/Sites), after hanging for a long time I get the response ping: cannot resolve test.dev: Unknown host

Here's what I've already done:

• I've gone through the Laravel Valet docs and everything installed fine.
• Apache is not running
• /etc/hosts contains no mention of test.dev
• I'm on valet v1.1.12
• I've restarted my computer
• I've installed php 7.0.7 via homebrew fresh and --with-fpm
• My $PATH contains $PATH:$HOME/.composer/vendor/bin
• sudo lsof -n -i:80 | grep LISTEN returns the caddy proc
• brew services list returns dnsmasq and is started
• I've updated brew, run brew doctor and all is good there
• I can start and stop valet successfully.
• valet paths returns successfully: [ "/Users/nateritter/.valet/Sites", "/Users/nateritter/Sites" ]
• Using valet link inside the test directory has no effect on this issue

Now, in addition to all this, I decided to try all the valet arguments out. valet share seemed to bork with an error at one point, which is interesting but I'm not sure it has anything to do with the original issue.

ERROR: Tunnel 'command_line' specifies invalid address 'test.dev:80': unexpected '[' in address test.dev:80

After this I get 21 lines of Failed to connect to 127.0.0.1 port 4040: Connection refused and then an exception:

[Httpful\Exception\ConnectionErrorException]                                                                              
Unable to connect to "http://127.0.0.1:4040/api/tunnels": 7 Failed to connect to 127.0.0.1 port 4040: Connection refused                                                                                                                              

fetch-share-url

Answer 1

The problem ended up being something to do with dnsmasq. Using the very thorough this answer to another related SO post, I ended up doing the following to solve my issue:

brew unlink dnsmasq

brew install dnsmasq

brew prune

brew services restart dnsmasq

valet install

Then, just to test before I did a ping, I did dig test.dev and the response included:

;; ANSWER SECTION:
test.dev.       3599    IN  A   127.0.53.53

I'm not sure why the IP is 127.0.53.53 and not 127.0.0.1 but when I did a ping test.dev it did return ...

PING test.dev (127.0.0.1): 56 data bytes
64 bytes from 127.0.0.1: icmp_seq=0 ttl=64 time=0.036 ms
64 bytes from 127.0.0.1: icmp_seq=1 ttl=64 time=0.072 ms

Browsing to test.dev worked as well.

One thing to note that I haven't looked into yet is that index.htm is not recognized by valet/caddy as a potential index file. Not part of the issue, but something interesting to note.