I'd probably have to do it in powershell if I wanted it to check every few minutes (essentially running 24/7 or whenever the computer is on) I assume? I'm still kinda new to scripting and completely new to WinSCP. I just recently switched over because of the automating capabilities. But say I wanted it to upload any *.png files in my C:\drawings folder to my server via sftp and then delete it locally after it's been fully uploaded. Or straight up moving it works too if that's possible.
If I understand you correctly, you just need a script that does:
put -delete "C:\local\path\*.exe" "/remote/path/"
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