Hi,
In this post a problem similar to yours has been addressed, you can try to adapt it to your situation.
Autoconnect USB device no longer works in VMWare Workstation 15
Other documentation:
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.
Select the Machine a USB Device Connects To
USB Auto connect to virtual machine
- USB devices can automatically connect to a powered on virtual machine when you configure Workstation 15 Pro to remember the connection rule. This is a Windows host only feature.
VMware Workstation Pro 15.0 - Neowin
ARomeo
Blog: https://www.aleadmin.it/