Two softwares - two programs - one trigger
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@oz-perrenoud you may need to create a batch file for this use this link for a walk though https://www.google.com/amp/s/www.makeuseof.com/tag/launch-multiple-programs-single-shortcut-using-batch-file/amp/
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@oz-perrenoud, here's another idea for you. Put "start " at the beginning, like this:
start C:\Windows\System32\notepad.exe && C:\Windows\System32\calc.exe
The "start" command exits right after it spawns Notepad so it runs the next command, calc.exe immediately.
I tried it and it worked for me.