Here is a basic example using the openssl ca to generate certificate database for use with a Certificate Revocation List and to check over Online Certificate Status Protocol.
To get started, you can run make prep to generate the initial root certificate authority, an OCSP signing cert, one leaf certificate, and another leaf certificate to be revoked.
Once that's done, have a look have a look at the empty CRL, and note that the x509v3 CRL Number is 0:
$ make inspect-crl
openssl crl -text -noout -in root/data/crl/crl.pem
Certificate Revocation List (CRL):
Version 2 (0x1)
Signature Algorithm: sha256WithRSAEncryption
Issuer: /C=US/ST=California/L=San Francisco/OU=Operations/CN=Fake Root CA/emailAddress=fakeroot@example.org
Last Update: Jun 21 00:03:30 2020 GMT
Next Update: Jun 21 00:03:30 2021 GMT
CRL extensions:
X509v3 Authority Key Identifier:
keyid:01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
DirName:/C=US/ST=California/L=San Francisco/OU=Operations/CN=Fake Root CA/emailAddress=fakeroot@example.org
serial:CB:98:8D:9B:A0:7C:48:CD
X509v3 CRL Number:
0
No Revoked Certificates.
Signature Algorithm: sha256WithRSAEncryption
a1:7d:c0:2a:c1:db:01:f2:28:74:be:1a:06:0f:7b:5f:1d:10:
f0:4d:60:b4:f2:61:72:e8:d2:ab:45:04:74:d8:4c:93:20:07:
a7:ec:bc:b9:34:a0:82:98:35:2c:cd:8a:2f:e2:a4:d1:87:09:
49:40:35:72:c3:ac:79:ab:4d:16:47:bb:92:06:45:ac:bd:91:
3e:c8:97:ed:28:b6:c2:98:d1:b6:a2:1f:c2:ce:8f:1d:5c:a1:
99:95:22:05:a7:6b:bb:78:e5:7b:c9:49:10:18:9d:91:f0:de:
c5:f1:a9:a0:87:08:91:7d:ba:51:22:2a:4e:64:58:e1:38:82:
f4:6d:77:be:d7:e2:91:bb:65:f9:ae:76:f1:e6:9c:53:27:71:
ad:39:08:60:6b:9d:f8:b4:f1:f4:71:48:0f:c3:27:a2:59:9d:
fa:e4:96:09:00:50:a2:4a:6b:87:f6:a0:64:42:93:fe:31:58:
cf:b9:e9:0e:40:6a:36:f3:ba:80:e5:cd:4d:14:37:ea:a2:5e:
54:54:00:79:eb:b1:9f:91:6b:10:93:ee:ca:c1:95:d8:4a:b7:
f6:07:d9:5a:73:57:f5:6a:2b:5a:de:82:49:82:f7:39:f1:ac:
25:b2:b7:a3:97:a2:f0:cd:61:29:21:80:03:ea:be:d8:36:60:
b9:8e:5d:7d
Now, let's verify that both certificates are valid and not on the CRL:
$ make check-leaf-crl check-leaf-revoked-crl
cat root/ca.crt root/data/crl/crl.pem > root/data/crl/bundle.pem
openssl verify -extended_crl -verbose -CAfile root/data/crl/bundle.pem -crl_check leaf/leaf.crt
leaf/leaf.crt: OK
openssl verify -extended_crl -verbose -CAfile root/data/crl/bundle.pem -crl_check leaf-revoked/leaf.crt
leaf-revoked/leaf.crt: OK
We can also verify these via OCSP. However, the standard version of OpenSSL that ships with macOS is LibreSSL 2.6.5, which won't work for this. You'll want openssl 1.1 or later, which can be installed via brew. Here's an example of running the ocsp checks using openssl@1.1:
$ OPENSSL=/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl make test-ocsp-ok test-ocsp-revoked
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-index root/data/index.txt -port 8080 \
-rsigner ocsp-signer/ocsp.crt -rkey ocsp-signer/ocsp.key -CA root/ca.crt -out root/data/log.txt & \
PID=$!; \
sleep 1; \
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-CAfile root/ca.crt -issuer root/ca.crt \
-cert leaf/leaf.crt -url http://127.0.0.1:8080; \
kill -TERM ${PID}
ocsp: waiting for OCSP client connections...
Response verify OK
leaf/leaf.crt: good
This Update: Jun 21 00:04:26 2020 GMT
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-index root/data/index.txt -port 8080 \
-rsigner ocsp-signer/ocsp.crt -rkey ocsp-signer/ocsp.key -CA root/ca.crt -out root/data/log.txt & \
PID=$!; \
sleep 1; \
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-CAfile root/ca.crt -issuer root/ca.crt \
-cert leaf-revoked/leaf.crt -url http://127.0.0.1:8080; \
kill -TERM ${PID}
ocsp: waiting for OCSP client connections...
Response verify OK
leaf-revoked/leaf.crt: good
This Update: Jun 21 00:04:27 2020 GMT
Next, we can revoke a certificate using the reason of "Key Compromise":
$ make revoke
OPENSSL_CONF=root/ca.conf openssl \
ca -revoke leaf-revoked/leaf.crt -crl_reason keyCompromise
Using configuration from root/ca.conf
Revoking Certificate 01.
Data Base Updated
OPENSSL_CONF=root/ca.conf openssl ca -gencrl -out root/data/crl/crl.pem
Using configuration from root/ca.conf
If we inspect the CRL now, you'll see the revoked cert and that the x509v3 CRL number has incremented to 1:
$ make inspect-crl
openssl crl -text -noout -in root/data/crl/crl.pem
Certificate Revocation List (CRL):
Version 2 (0x1)
Signature Algorithm: sha256WithRSAEncryption
Issuer: /C=US/ST=California/L=San Francisco/OU=Operations/CN=Fake Root CA/emailAddress=fakeroot@example.org
Last Update: Jun 21 00:04:46 2020 GMT
Next Update: Jun 21 00:04:46 2021 GMT
CRL extensions:
X509v3 Authority Key Identifier:
keyid:01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
DirName:/C=US/ST=California/L=San Francisco/OU=Operations/CN=Fake Root CA/emailAddress=fakeroot@example.org
serial:CB:98:8D:9B:A0:7C:48:CD
X509v3 CRL Number:
1
Revoked Certificates:
Serial Number: 01
Revocation Date: Jun 21 00:04:46 2020 GMT
CRL entry extensions:
X509v3 CRL Reason Code:
Key Compromise
Signature Algorithm: sha256WithRSAEncryption
66:b8:f6:31:e7:d3:c5:31:ca:eb:dd:a2:36:5e:65:4f:aa:2a:
e9:55:81:90:c3:13:57:4e:e3:cd:03:02:54:21:79:26:9d:7e:
a6:2e:b2:f5:03:1c:52:2b:29:95:8c:93:21:64:84:6d:d5:a2:
07:19:1a:d7:a1:f4:51:e9:19:a2:27:4b:05:d2:2f:51:26:39:
e9:43:95:55:d9:85:7d:0f:83:99:3e:f5:7b:4d:1f:54:c2:04:
30:41:f6:e6:4a:13:d8:e8:74:84:99:36:3a:0d:fb:80:ff:0e:
3b:47:20:d5:96:ac:f3:99:8b:f2:38:6b:ef:94:b3:72:eb:84:
c9:3a:74:10:2d:93:28:2d:32:62:8c:e7:d9:2e:8f:86:b3:17:
c3:72:c8:0d:ba:4a:18:59:b1:20:bc:5d:0d:af:64:8f:53:f5:
22:1f:8c:45:ab:a8:48:24:6c:35:bf:e0:e4:9f:7e:5b:f4:2a:
71:80:8d:30:40:63:53:5b:bb:2d:61:88:32:ec:89:15:47:c4:
9e:f9:28:dc:5c:1a:a0:67:79:f8:d3:49:18:c1:49:0d:3f:02:
61:9a:e4:db:5a:f5:21:0f:79:84:5c:b6:3c:38:76:ba:69:97:
eb:ef:d6:0b:d9:d7:77:79:57:c6:48:00:89:4a:62:59:75:f1:
81:42:f9:96
Also, the we can see that checking the revoked cert against the CRL confirms revocation:
$ make check-leaf-revoked-crl
cat root/ca.crt root/data/crl/crl.pem > root/data/crl/bundle.pem
openssl verify -extended_crl -verbose -CAfile root/data/crl/bundle.pem -crl_check leaf-revoked/leaf.crt
leaf-revoked/leaf.crt: CN = www2.example.org, ST = California, C = US, OU = My Example Website 2, emailAddress = user@example.org
error 23 at 0 depth lookup:certificate revoked
make: [check-leaf-revoked-crl] Error 2 (ignored)
But the non-revoked cert continues to verify as OK:
$ make check-leaf-crl
cat root/ca.crt root/data/crl/crl.pem > root/data/crl/bundle.pem
openssl verify -extended_crl -verbose -CAfile root/data/crl/bundle.pem -crl_check leaf/leaf.crt
leaf/leaf.crt: OK
And we can check the same things over OCSP:
$ OPENSSL=/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl make test-ocsp-ok test-ocsp-revoked
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-index root/data/index.txt -port 8080 \
-rsigner ocsp-signer/ocsp.crt -rkey ocsp-signer/ocsp.key -CA root/ca.crt -out root/data/log.txt & \
PID=$!; \
sleep 1; \
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-CAfile root/ca.crt -issuer root/ca.crt \
-cert leaf/leaf.crt -url http://127.0.0.1:8080; \
kill -TERM ${PID}
ocsp: waiting for OCSP client connections...
Response verify OK
leaf/leaf.crt: good
This Update: Jun 21 00:05:55 2020 GMT
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-index root/data/index.txt -port 8080 \
-rsigner ocsp-signer/ocsp.crt -rkey ocsp-signer/ocsp.key -CA root/ca.crt -out root/data/log.txt & \
PID=$!; \
sleep 1; \
/usr/local/Cellar/openssl@1.1/1.1.1g/bin/openssl ocsp \
-CAfile root/ca.crt -issuer root/ca.crt \
-cert leaf-revoked/leaf.crt -url http://127.0.0.1:8080; \
kill -TERM ${PID}
ocsp: waiting for OCSP client connections...
Response verify OK
leaf-revoked/leaf.crt: revoked
This Update: Jun 21 00:05:56 2020 GMT
Reason: keyCompromise
Revocation Time: Jun 21 00:04:46 2020 GMT
Lastly, if you want to inspect all of the x509v3 extensions for the certificates, you can do so like this:
$ make inspect-extensions
ROOT:
X509v3 extensions:
X509v3 Basic Constraints: critical
CA:TRUE, pathlen:0
X509v3 Subject Key Identifier:
01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
X509v3 Authority Key Identifier:
keyid:01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
X509v3 Key Usage: critical
Digital Signature, Certificate Sign, CRL Sign
OCSP SIGNER:
X509v3 extensions:
X509v3 Basic Constraints: critical
CA:FALSE
X509v3 Subject Key Identifier:
99:17:A8:87:F4:04:24:38:48:06:6B:6F:8C:04:1D:1F:07:4D:0D:93
X509v3 Authority Key Identifier:
keyid:01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
X509v3 Key Usage: critical
Digital Signature, Non Repudiation, Key Encipherment
X509v3 Extended Key Usage:
OCSP Signing
LEAF:
X509v3 extensions:
X509v3 Basic Constraints: critical
CA:FALSE
X509v3 Subject Key Identifier:
23:58:8B:C5:DD:16:21:00:FE:61:E6:36:A0:10:D2:FA:D8:40:05:0C
X509v3 Authority Key Identifier:
keyid:01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
X509v3 Key Usage: critical
Digital Signature, Key Encipherment
Authority Information Access:
OCSP - URI:http://127.0.0.1:8080
CA Issuers - URI:http://crl.example.com/issuer.pem
X509v3 CRL Distribution Points:
Full Name:
URI:http://crl.example.com/crl.pem
X509v3 Subject Alternative Name:
DNS:www.example.org, DNS:office.example.org
LEAF REVOKED:
X509v3 extensions:
X509v3 Basic Constraints: critical
CA:FALSE
X509v3 Subject Key Identifier:
FC:65:B1:81:E1:54:18:3E:C3:B5:BC:48:EB:B6:30:4C:72:8D:40:BC
X509v3 Authority Key Identifier:
keyid:01:53:31:4D:4F:C9:17:44:CE:44:41:F9:D7:C7:07:48:D8:79:1D:5B
X509v3 Key Usage: critical
Digital Signature, Key Encipherment
Authority Information Access:
OCSP - URI:http://127.0.0.1:8080
CA Issuers - URI:http://crl.example.com/issuer.pem
X509v3 CRL Distribution Points:
Full Name:
URI:http://crl.example.com/crl.pem
X509v3 Subject Alternative Name:
DNS:www2.example.org, DNS:office2.example.org