Jamkazam keeps asking to reload app on Mac OSX

[GDJ]

I see, so you're saying he's always seeing the so called, New JK Applicaion message every time he starts the app, even though it's the latest. I agree with you that in part it could be Apple privacy & security settings however, i wonder if he is also running an IP sniffer like Little Snitch that is blocking and outbound call home to the JK server.

One suggestion. Download the stand alone installer form the home page.
Delete the current App, in the Application Folder
Install stand alone one, and launch it.