At some point, the connection between the management server and SmartDashboard gets corrupted.
The immediate result is a fatal failure in SSL HMAC verification, which leads to the SIC tunnel shutting down and the connection terminating. Once this occurs SmartDashboard will crash.
The source of the corruption is a memory overrun at the level of the NIC driver of VMware.
This is similar to a problem in VMware KB about data corruption after a Windows 2012 virtual machine network transfer.
WA #1 - changing the Ethernet Adapter driver type of the Windows 10 machine:
Instead of E1000E, (the default driver in Windows 10) that has a data corruption bug, E1000 should be used instead.
If using E1000E adapter as depicted above, it should be removed.
When adding a new adapter, in the Type field select E1000
You should see the this screen showing the new adapter-