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As per https://support.apple.com/en-in/HT210176: > TLS server certificates must contain an ExtendedKeyUsage (EKU) extension containing the id-kp-serverAuth OID. We were not specifying this EKU. Validated by checking with the old self-signed certs: $ security verify-cert -c webproxy_cert.pem -p ssl -r webproxy_cert.pem Cert Verify Result: Invalid Extended Key Usage for policy And then repeating the process after this change: $ security verify-cert -c webproxy_cert.pem -p ssl -r webproxy_cert.pem ...certificate verification successful. Closes #32531