It looks like the more recent releases of Azure CLI are running off Python versions that enforce ‘Authority Key Identifier’ checks of the security certificates when connecting to Azure CLI (az login). You might see an error message similar to the below if bumping into this issue. HTTPSConnectionPool(host=’login.microsoftonline.com’, port=443): Max retries exceeded with url: /organizations/v2.0/.well-known/openid-configuration (Caused by SSLError(SSLCertVerificationError(1, ‘[SSL: CERTIFICATE_VERIFY_FAILED]… Read more