Found my issue this morning.
For some reason, my second monitor was causing the popup to appear off screen. The only reason I came across this was because I went into the workspace mode on Mac and saw that the window was way off.
Disconnecting my 2nd monitor and proceeding was how I solved my issue.
Thanks for the help!
Oddly enough after a re-image on my work computer and re-installing Extensions I had this same problem this morning, on a Mac with second monitor. Thank you and Duck Duck Go for saving me hours of aggravation.