When going upwind, planing on a shortboard, slalom board, or formula board, how you set the rig is
not the only thing you need to "set up".
For sailing upwind you need your sail fairly flat, the boom fairly high, but most of all you need to get the
side to side (roll axis) of your board set correctly so you go upwind on lift from your fin.
Having the correct fin can make a huge difference.
Tip your board very slightly lee rail down and really push with your back foot "across the top of the board"
and maybe even "pull" a little bit upwind with your fornt foot.
This will cant the fin over slightly so the upwind rail is very slightly higher than the downwind rail.
You will go upwind really well as you are using the "lift" from the fin to take you there.
If you have a small fin or a curvy wave type fin (made to be "loose" but not spin out) you will have to tip your board so the upwind rail is lower than the downwind rail and use the shape in the bottom of the board
to take you upwind.
Hope this helps,