if windows is reporting “windows does not have enough information to verify this certificate”, it’s most likely indicating a broken certificate chain. viewing the certification path tab and examining the Trusted Root Certification Authorities store can verify this.

in the case that i was looking at, it looked like the root chain was missing Baltimore CyberTrust Root, Microsoft Internet Authority, & MSIT Machine Auth CA2. this site provides a download for those root certs:
https://corp.sts.microsoft.com/Onboard/CertRenewal.html

additional information here:
http://www.kozeniauskas.com/itblog/2011/06/27/windows-does-not-have-enough-information-to-verify-this-certificate/

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