I have a long history of success updating older Nuvi devices connecting via USB to older versions of Garmin Express on Windows 7 and 10 running in VMware Workstation Pro. This combination no longer works - Windows does not recognize the USB device, thus Garmin Express cannot connect to the device. In contrast, I frequently use USB connected scanners and various storage devices in the same way, connecting to Windows 7/10 applications running in VMware Workstation Pro virtual computers.
Currently using Garmin Express v7.16.1.0 for Windows 10 running in VMware Workstation v17.0.1 virtual computer running on a Ubuntu 20.04 Linux host.
My only Windows installations are within VMware virtual computers. Is there any way to connect my Drivesmart 55 to Garmin Express in this configuration or natively on Ubuntu Linux?