准备

需要openssl加载 pkcs11 engine。添加以下包到环境:

(openssl.override {
              conf = pkgs.writeText "openssl.conf" ''
                openssl_conf = openssl_init
                [openssl_init] 
                engines = engine_section
                ssl_conf = ssl_module 
                [engine_section] 
                pkcs11 = pkcs11_section 
                [pkcs11_section] 
                engine_id = pkcs11 
                dynamic_path = ${pkgs.libp11}/lib/engines/libpkcs11.so 
                MODULE_PATH = ${pkgs.opensc}/lib/opensc-pkcs11.so
                init = 0 
              '';
            })

正确加载的结果为：

> openssl engine -t
(rdrand) Intel RDRAND engine
     [ available ]
(dynamic) Dynamic engine loading support
     [ unavailable ]
(pkcs11) pkcs11 engine
     [ available ]

生成 root CA

*-ca.conf 文件可以从这里找到或见附录

$ openssl req -x509 -newkey ed25519 -days 10000 -config root-ca.conf -keyout root.key -out root.crt

导入key（可选）

# import key and certificate into yubike, in here I use slot 9c, which is Digital Signature
$ yubico-piv-tool -a import-key -s 9c -i root.key
$ yubico-piv-tool -a import-certificate -s 9c -i root.crt
$ yubico-piv-tool -a status -s 9c
# to view the content of the ca-cert
$ openssl x509 -text -in root.crt

Intermediate CA & CSR 生成

生成公钥

$ c(y)kman piv keys generate -a ED25519 --pin-policy ONCE --touch-policy CACHED 9c ./9c.pem

生成签名请求

$ yubico-piv-tool -a verify-pin -a request-certificate -s 9c -S '/CN=digi_sign/OU=test/O=nyaw.xyz/' -i
 ./9c.pem -o csr.pem -r canokey

用 ROOT CA 签名

WARNING

截止 17 Dec 02:29:29 canokey canary 3.0.0 于此方案存在问题，CSR被签名会出现报错且不成功，见discuss。Yubikey 5 NFC 经测试没有问题。

不存在硬件密钥A的情况，使用文件CA签：

$ openssl x509 -CAkey root.key -CA root.crt -CAcreateserial -req -days 3650 -in csr.pem -out inter.crt -extfile root-ca.conf -extensions inter_ca

使用密钥A, PIV签：

$ openssl x509 -engine pkcs11 -CAkeyform engine -CAkey id_2 -sha256 -CA root.crt -CAcreateserial -req -days 3650 -extfile root-ca.conf -extensions inter_ca -in inter.csr -out inter.crt

附 canokey canary 3.0.0 的报错:

Warning: CSR self-signature does not match the contents
Certificate request self-signature did not match the contents
40172E747B7E0000:error:06880006:asn1 encoding routines:ASN1_item_verify_ctx:EVP lib:crypto/asn1/a_verify.c:218:
40172E747B7E0000:error:06880006:asn1 encoding routines:ASN1_item_verify_ctx:EVP lib:crypto/asn1/a_verify.c:218:

导入Intermediate CA证书

yubico-piv-tool -a import-certificate -s 9c -i inter.crt

附录

# root-ca.conf
[req]
x509_extensions=root_ca
distinguished_name=req_distinguished_name
prompt=no

[req_distinguished_name]
O=Milieuim
CN=Milieuim Root CA

# see https://www.openssl.org/docs/manmaster/man5/x509v3_config.html
[root_ca]
subjectKeyIdentifier=hash
# the root CA has pathlen:1, inter CA has pathlen:0
basicConstraints=critical,CA:true,pathlen:1
keyUsage=critical,keyCertSign,cRLSign

# sign intermedia CA cert with the following extension, the only diff is pathlen
[inter_ca]
subjectKeyIdentifier=hash
# the root CA has pathlen:1, inter CA has pathlen:0
basicConstraints=critical,CA:true,pathlen:0
keyUsage=critical,keyCertSign,cRLSign

# inter-ca.conf

[req]
req_extensions=inter_ca
distinguished_name=req_distinguished_name
prompt=no

[req_distinguished_name]
O=Milieuim
CN=Milieuim Intermediate CA 0

# see https://www.openssl.org/docs/manmaster/man5/x509v3_config.html
[inter_ca]
subjectKeyIdentifier=hash
basicConstraints=critical,CA:true,pathlen:0
keyUsage=critical,keyCertSign


# signing server certs with the following extensions
[server_cert]
subjectKeyIdentifier=hash
basicConstraints=critical,CA:false
keyUsage=critical,digitalSignature,keyEncipherment
extendedKeyUsage=serverAuth,clientAuth


[client_cert]
subjectKeyIdentifier=hash
basicConstraints=critical,CA:false
keyUsage=critical,digitalSignature,keyEncipherment
extendedKeyUsage=clientAuth,emailProtection

[code_signing_cert]
subjectKeyIdentifier=hash
basicConstraints=critical,CA:false
keyUsage=critical,digitalSignature
extendedKeyUsage=codeSigning

顺便，如果要签署终端server域名证书，参考：

# domain.conf

[ req ]
req_extensions = v3_ext
distinguished_name = dn
prompt = no
default_md = sha256

[ dn ]
CN = *.nyaw.xyz

[ v3_ext ]
basicConstraints = CA:FALSE
keyUsage = nonRepudiation, digitalSignature, keyEncipherment
subjectAltName = @subject_alt_name
extendedKeyUsage = serverAuth, clientAuth

[subject_alt_name]
DNS.1 = nyaw.xyz
DNS.2 = *.nyaw.xyz