This was a all around fail! As soon as the servers were available (previous DJ disconnected) I clicked Options - Enable Live Broadcast and immediately got a Failed on both connections. (See image) It didn't seem to want to retry the connections. I had to revert to other DSP / Encoders. I tried it again at the end of my show. So I know I disconnected the 3rd party encoder before clicking Enable.

Starting with version 1.9, Mixxx allows live broadcasting, supporting Shoutcast and Icecast streaming servers. Installing and configuring Icecast and Mixxx to create your own Internet radio station 1. Install Icecast. Icecast can be installed either on a separate server, or on the same computer that will be running Mixxx to broadcast.
Pushed some changes that should now make this actually better. Reading little bit libshout code and noted that aether get connection or end up to misery. Thinking this through made me sure there is no need for these extra delays because trying to open socket will take care of this (if network is slow and if it's fast it doesn't matter anyway).
Oct 31, 2016 How to setup Mixxx to broadcast to your online radio station. Mixxx is free and it's available for Windows, Mac, and Linux systems, however this guide focuses on a Mac setup - https://radio.co.

Socket Error Mac

Starting with version 1.9.0, Mixxx directly supports live broadcasting which allows you to connect to Shoutcast and Icecast servers. Using the preferences dialogue, you can simply supply Mixxx with all information needed to establish a server connection. To enable live broadcasting you can either use the options menu or the checkbox within the preference dialogue.

For an Icecast server, you'll need to provide the mount point (of the form “/mount”). You can enter the host as either a host name or an IP address. In the “login” field, the default is to enter “source” – without this, you will not connect successfully to the server. The password will be provided by your streaming server provider, unless you run your own radio server.

Do not enter a URL as the host! “http://example.com:8000” does not work. Use “example.com” in the host field and “8000” in the port field instead.

If you connect to an Shoutcast server the default login name is “admin”. It is not necessary to specify a mount point. The password will be provided by your streaming server provider.

An Icecast server can stream either mp3 or Ogg. However, although Ogg is more efficient and effective - you get a better sound than mp3 at a lower data rate - not all players can play Ogg streams, so as a result mp3 is probably a better choice unless you know your listeners can hear an Ogg stream successfully. You may need the LAME libraries to stream in mp3. See the next section for details.

Socket Error 11004

By default, Mixxx broadcasts artist and title information to your listeners. You can disable this feature by selecting “enable custom metadata”. For technical reasons, broadcasting artist and title information is not supported for OGG streams.

Mixxx Socket Error