Looks like, from your screen shot, categories can be moved up/down, but courses can't. The check box is for including courses in the "Move selected x to' at the bottom of that display.
However, in mine, I have up/down arrows in the courses listing of a category! Course listing should also have that big + (left) ... the 'drag and drop' tool for lack of a better diz.
Using Boost or Classic theme? or other?
What's the exact version with build date? 3.7.0 with X? or is it 3.7.2 (Build: 20190909) released just the other day?
'SoS', Ken