Generate a private key (priv.pem): $ openssl genrsa -out priv.pem 2048 Generate 2 self-signed certificates from this key (pub.pem, pub-other.pem): $ printf '.\n.\n.\n.\n.\nlocalhost\nhg@localhost\n' | \ openssl req -new -x509 -key priv.pem -nodes -sha256 -days 9000 -out pub.pem $ printf '.\n.\n.\n.\n.\nlocalhost\nhg@localhost\n' | \ openssl req -new -x509 -key priv.pem -nodes -sha256 -days 9000 -out pub-other.pem Now generate an expired certificate by turning back the system time: $ date --set='2016-01-01T00:00:00Z' $ printf '.\n.\n.\n.\n.\nlocalhost\nhg@localhost\n' | \ openssl req -new -x509 -key priv.pem -nodes -sha256 -days 1 -out pub-expired.pem Generate a certificate not yet active by advancing the system time: $ date --set='2030-01-01T00:00:00Z' $ printf '.\n.\n.\n.\n.\nlocalhost\nhg@localhost\n' | \ openssl req -new -x509 -key priv.pem -nodes -sha256 -days 1 -out pub-not-yet.pem Note: When adjusting system time, verify the time change sticks. If running systemd, you may want to use `timedatectl set-ntp false` and e.g. `timedatectl set-time '2016-01-01 00:00:00'` to set system time. Generate a passphrase protected client certificate private key: $ openssl genrsa -aes256 -passout pass:1234 -out client-key.pem 2048 Create a copy of the private key without a passphrase: $ openssl rsa -in client-key.pem -passin pass:1234 -out client-key-decrypted.pem Create a CSR and sign the key using the server keypair: $ printf '.\n.\n.\n.\n.\n.\nhg-client@localhost\n.\n.\n' | \ openssl req -new -key client-key.pem -passin pass:1234 -out client-csr.pem $ openssl x509 -req -days 9000 -in client-csr.pem -CA pub.pem -CAkey priv.pem \ -set_serial 01 -out client-cert.pem When replacing the certificates, references to certificate fingerprints will need to be updated in test files. Fingerprints for certs can be obtained by running: $ openssl x509 -in pub.pem -noout -sha1 -fingerprint $ openssl x509 -in pub.pem -noout -sha256 -fingerprint