I suggest using QEMU/KVM with automatic USB redirection, I updated my Dualsense yesterday that way with no problems. iirc automatic USB redirection is available on VirtualBox too.
Hold up... There's a PC app that can update the firmware without plugging it back into the PS5? 😮
Can I get a link? And will this also allow me to check the battery level?
A quick search led me here, which looks like what OP is using based on the screenshots: https://controller.dl.playstation.net/controller/lang/en/2100004.html
The app is most likely disconnecting and reconnecting the controller or making it connect as another device through the process the moment that happens the device is not passed back through or not as the fully same device so apps fail.
This is similar to things like VR and boom microphones
I'm not familiar with this app, but have you tried running it under Linux with WINE instead of in a Windows VM?
Wine does not have system level USB access.
No firmware updates or low-level communication will work.
That's why no-one is running the official razer, corsair, logitech etc. mouse/keyboard whatever programs on linux.
it tried doing that at first but it requires .net 8 to even run and to be honest im not familiar enough with wine to be able to install multiple programs to the same wine prefix
Winetricks is your friend and makes that stupid easy. Gui program that let's you just click to install common things like .net or vc++
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