Just to close the loop on this one - it was a fairly simple fix in the end. To create a self-signed cert (to enable Meraki Client VPN via AD auth to work): PowerShell (admin) and run the command New-SelfSignedCertificate -DnsName "servername.fqdn.domain" -KeyAlgorithm RSA -KeyLength 2048 -CertStoreLocation "Cert:\LocalMachine\My" -NotAfter (Get-Date).AddYears(10) Hit your Windows Key and type “Cert” and click on Manage Computer Certificates Go to Personal > Certificates and see your new Cert that you just created Right-click the new Cert and go to All Tasks > Export Yes, export the private key Personal Information Exchange, check the following: Include all certificates Export all extended properties Check Password: Make a password you’ll remember Browse to an easy to remember location like C:\Certs and Finish Expand Trusted Root Certificate Authorities, right click Certificates > All Tasks, Import… Choose your cert, enter the password, make sure importing is a success Test Note: DO NOT DELETE the certificate from Personal > Certificates - it needs this one otherwise Auth will continue to fail.
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