Sailpoint_User Have you tried removing that cert and creating another one? This is a CryptographicException that occurred when trying to look at the content type of the cert. You can download a copy of PSServicePrincipal from https://www.powershellgallery.com/packages/PSServicePrincipal/1.0.11 and running the following: New-SelfSignedCert -CertificateName test2 -DnsName test2 -SubjectAlternativeName test2 -Password (ConvertTo-SecureString 'test' -AsPlainText -force). NOTE: If you are running Windows Version 2004 you will now need to run powershell as administrator for PSServicePrincipal to create self-signed certificates due to a change in the security provider. Try with that and see if you get the same thing. I also see that your version if framework is pretty old.