I think this issue began after the 1903 update. In the past, I have always been able to connect to a VPN by clicking on the networking icon in the system tray, selecting the desired VPN from the list, and clicking the ‘Connect’ button. The VPNs that have a password saved in the system connect without any issues, but the ones that do not have a password saved (I use WiKID to generate a dynamic password) just spin and never prompt for a password.

Here are my current settings:

This is my VPN Adapter Security properties:

I haven’t been able to find any reports of this issue online. I have tried deleting and recreating the VPN connection, but I still experience the same issue. While I am aware of alternative ways to launch a VPN connection, I am specifically trying to find a way to get the built-in method to work properly again, including prompting for a username and password.

Note: When I go through the VPN page in the Windows Settings and click the ‘Connect’ button, the prompt appears as expected.

Event Viewer message generated when attempting to connect to VPN through system tray:

Askify Moderator Edited question April 25, 2023