Level and stable are 2 different things...
For best stability - yes - you want all 4 down.
DW can tell when one isn't making contact... lol
Once auto-level if a jack isn't down - you should be able to switch to manual and lower front or rear jacks (based on the one still up) till it touches... Its smart enough not to move the other one in pair that is extended/down until the other one 'catches up'...
Manual leveling - best I found was:
- lower front till touching
- lower rear till touching
- follow the arrows for the rest.