Why does auto-orient keep failing?

Check the following directories and check to see whether a config.json file can be found in both:

C:\ProgramData\Leap Motion

C:\Users\USERNAME\AppData\Roaming\Leap Motion

If you do see the files, open up services.msc, stop "Leap Service" and quit out of the Leap Motion Control Panel. Then, delete the config.json files, reboot your computer, and try enabling auto-orient tracking to see if the setting persists through another system reboot.