Would I use で if I want to say “drawing in an art program”


I feel like this is wrong, but I’m not entirely sure, if I wanted to say “my
first time drawing in Paint Tool Sai” would this sentence be correct?

ペイントツールSAIで初めて描画




Your use of で is perfectly fine. 描画 is a suru-verb meaning "to draw" or "(an
act of) drawing". It is more suitable for geometric or technical drawing, like
what you make with a CAD tool, a graph tool or Adobe Illustrator. An artwork
typically created with SAI is usually called an イラスト, 絵, etc. How about:

  * ペイントツールSAIで初めて描いたイラスト
  * 初めてペイントツールSAIで作った絵

