Power-cycling needed every time I upload firmware

Anyone knows if this is normal? Every time i try to upload firmware in a Pixhawk 4 the message below appears but the upload is never initiated. I have to manually reboot the board. Any workarounds perhaps?

I am using WSL2 and followed the appropriate guide from the docs.
image

Solved.

It seems that the board had an old bootloader. Updating it solved the issue. Uploading from wsl2 with windows10 possible.