Administrators who have deployed Windows 10 Always On VPN may encounter a scenario in which an Always On VPN connection fails, yet the connectivity status indicator perpetually reports a “Connecting” status.
Affected Clients
This is a known issue for which Microsoft has recently released updates to address. Affected clients include Windows 10 1909, 1903, and 1809.
Updates Available
The following Windows updates include a fix to resolve this problem.
KB4541335 – Windows 10 1909 and 1903
KB4541331 – Windows 10 1809