Windows Meraki Sentry VPN prompting for credentials

[IT_Magician]

We have a VPN profile pushed via Sentry to both Windows and MAC devices. All MAC devices work fine, and most Windows devices work fine, but we have a handful of Windows devices that cannot connect to the VPN. I spun up a fresh Windows 11 VM and can re-create the issue.

The VPN shows up, but when connecting it is prompting for a username and password instead of Meraki systems manager automatically handling that. When looking in the event viewer I do see errors with the profile installing. I removed and re-pushed the profile but the errors in event viewer still are listed (even through the VPN does install) but I think that might have something to do.

I am spinning up a Windows 10 device now to test that OS.

[IT_Magician]

Alright, spun up a new Windows 10 box and confirmed issue is there as well. Meraki pushes out the VPN profile but when I connect it prompts for a username and password. I am going to try and downgrade the Meraki version. We are currently using latest of 3.5.2.

[IT_Magician]

Received this update from Meraki support. At least they know the issue but that leaves us dead in the water.

"The Meraki Engineering team finished investigating the behaviors with Windows 10 & 11 devices and Sentry VPN. The Windows 10 & 11operating system introduced a change in what type of logins and credentials can be used in an MDM environment. Sentry Client VPN was original designed using a method that Windows no longer allows by default and leads to the user being prompted to enter their credentials. 

As this is directly related to a change in Windows 10 & 11 behavior and the Sentry Client VPN integration we are currently investigating and tracking improvement on this issue moving forward, however I do not have any further updates on the improvement at this time."