Here's what I discovered. The password entry in the new wifi connection tab IS NOT USED when the raspberry attempts to join a network for the first time. Instead, the raspberry drops off the current network, THEN prompts the user to manually enter the password, it times out because this prompt can't be seen by the user, the raspberry then restarts the astroberry hotspot without ever joining the new connection.
The only way to discover this fault is to physically connect KVM peripherals to the raspberry (which is not possible in a headless installation) or... (as I did) connect a physical ethernet cable between the router and raspberry then select the new wifi connection. These two methods are the only way a user can interact with the "secret" password prompt which only comes up after the wifi connection is broken.

Read More...