I have a server that hosts VMware workstation Pro 15. Has like 6 virtuals on it. 5 of those I have USB removed from them. The 6th has it enabled and has a USB cable attached outside to a device. Everytime I turn off the virtual and on again I have to go on the console while booting and click it in the bottom right corner to enable to device during boot. Very annoying. Is there a way to automate mounting a USB connected device on a specific virtual (not the one always in the foreground)?
In this post a problem similar to yours has been addressed, you can try to adapt it to your situation.
A USB device is treated as new when Workstation Pro does not have a remembered connection rule for the USB device. A connection rule is remembered when you select Remember my choice and do not ask again, and stays remembered until you configure Workstation Pro to forget the rule.
USB Auto connect to virtual machine