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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

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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
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