If this helps anyone in the future, I had to visit on two different devices the URL location of where the chat_content.html is located:
[piratebox.lan]
there I only saw the first anonymous default message - but it seems like refreshing that page again - all my other messages appeared.
After this, the device I was using was now able to receive all of the messages as they were being transmitted.
I had to do the same steps for my mobile device. 1) Visit that URL, 2) Refresh 3) Go back to the shoutbox
[piratebox.lan]
there I only saw the first anonymous default message - but it seems like refreshing that page again - all my other messages appeared.
After this, the device I was using was now able to receive all of the messages as they were being transmitted.
I had to do the same steps for my mobile device. 1) Visit that URL, 2) Refresh 3) Go back to the shoutbox