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Chrome 75+ started to strictly enforce X.509 keyUsage against TLS server certificates. Webrick supports generating instant self-signed certificates for debugging purpose and these certificates lacks required keyUsage for modern TLS. So adding the following keyUsages: - digitalSignature (for server authentication) - keyAgreement (for DH key exchange) - dataEncipherment (for data encryption) References: - https://tools.ietf.org/html/rfc5280#section-4.2.1.3 - https://crbug.com/795089 - https://boringssl-review.googlesource.com/c/34604