Trouble connecting Drivesmart 55 EX to Garmin Express Windows 10

I believe it’s a lower level problem, ie outdated Windows MTS drivers such as those distributed via the Garmin web site.  

I am continuing to research and found many references to getting an MTS driver load failure error when Windows detects the Garmin USB connecting to the computer.  That fits my earliest symptoms.

I also confirmed that the Garmin device USB connection is being passed though the VMware host to the virtual machine, as is done for other devices. So, nothing strange about that.

Given that Garmin Express does not support Linux and connecting to Garmin Express running in a virtual machine running Windows no longer works, how about a platform independent web/browser-based solution? Does that exist, yet?

While I do not have a Drivesmart anymore (its firmware was disproportionately riddled with issues for my taste, however the same applies for most of my Garmin devices), it should show up in your Ubuntu host as MTP and it may fail to connect in the event you try to mount it, however you might verify that is properly connected by issuing lsbusb command from the shell which should return (amongst all the USB devices connected) its Bus/Device/ID/Descriptor (the latter being Drivesmart MTP or something, from memory); in the event that does not happen, you might want to inquire what went wrong, i.e. by issuing sudo journalctl -b | grep -e ‘not accepting address’ -e ‘couldn’t allocate usb_device’ as the culprit could be the cable, the USB port and – most possibly (that happened in my case) the device itself. If all is well on the host side, let’s move on to the Windows 10 guest: since you mentioned that your scanners and/or USB storage is working properly, we can exclude issues with the VMware USB passthrough, therefore your EX – although it could show as unrecognized under Universal Serial Bus Controllers – should be enumerated in the Device Manager. Now, I would avoid the Garmin MTS drivers  if I were you (latest, outstandingly buggy, version is – again from memory – from 2015) and use Garmin Express instead, which in its current release 7.16.1.0 has some issues related to the way it connects to the Garmin infrastructure worldwide (short version: it may work fine for, for example, a Jon from West Sussex, however it may return a “We’re unable to add this device” to a Bruce from Melbourne): in the event you’re affected by the latter, downgrade Express to 7.15.x.0. Finally, if all else fails, you may want to experiment by changing VMware USB controller’s USB Compatibility to “USB 1.1” and see what happens.

As for your last - interesting - question, you’re probably referring to the current W3C’s (et al.) attempt to push a functional and cross-platform WebUSB API: while it is technically within the realm of feasibility, vendors’ implementations will turn it into an effort like herding cats. So… no, not happening soon, IMO.