/etc/hosts file not redirecting to local application on mac

Question

I've set up a redirect in the hosts file on my machine that basically points an auth domain to my local project in IIS (when run in Visual Studio for Mac) - however when I type the domain name into Chrome (for example), I get a message saying this site cannot be reached.

The local URL I want this to point to is: http://localhost:44380/ - the live URL I can't reveal for security but lets say for the sake of this example that it's: auth.site.com (the actual URL I'm using is valid and it does load in Chrome)

Here's my hosts file from terminal as it's currently set up:

##
# Host Database
#
# localhost is used to configure the loopback interface
# when the system is booting.  Do not change this entry.
##
127.0.0.1       localhost
255.255.255.255 broadcasthost
::1             localhost
127.0.0.1       auth.site.com

I'm very familiar with windows and how the hosts file works, so from what I know there this would work in windows (I think anyways), is there something I'm missing here because obviously something isn't right?

Answer 1

I would first check where the problem is exactly. I think of the following possible issues:

1. Hosts file not properly working: Try running ping auth.site.com in a terminal. If you see responses from 127.0.0.1 this should work.
2. Is access to the port possible, open http://localhost:44380 in your browser. If you see your page, this should work.
3. Combine the two parts: open http://auth.site.com:44380 in your browser. If this does not work, maybe there are security features from the original page you visited before preventing access (like forcing SSL or a pinned certificate).
4. Try another browser or curl auth.site.com:44380 in a terminal.

If you are not happy with the given ports, you can do a port forwarding. Changing ports is not possible in the hosts file, because the hosts file is only for domain name lookup and this has nothing to do with the ports.