However, the Dashboards screen item shows up at the bottom of the menu:
If I set the insertBefore to “Administration”, it places the item above Administration and below Application. It just isn’t working to move the item above Application.
It’s counter-intuitive, but if you place your <item insertBefore="application"/>after the application menu, it will be shown before. The reason is the menu config is processed in one pass from top to down.
This is true to both CUBA and Jmix, but please post questions on Jmix at forum.jmix.io. And prefer text over screenshots, it would be easier to copy-paste code for those who answer.