Beginning with Chrome 58, certificates using only CN without Subject Alternative Name(s) will not be accepted. The WebUI & openSSL configuration for generating CSRs needs to be updated for these fields. Please also allow more than one SAN; it's great to have the certificate valid for both the web filter's IP & DNS name. (Yes, I'm currently running this config; CSR generated on another computer).
Secure Administration - CSR needs to include Subject Alternative Name(s) for Chrome 58+
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