Kroko Just another WordPress weblog

using openssl
using keytool (included in recent Sun java reference implementations)

openssl

generate a new private key and matching Certificate Signing Request (eg to send to a commercial CA)

openssl req -out MYCSR.csr -pubkey -new -keyout MYKEY.key

add -nodes to create an unencrypted private key
add -config <openssl.cnf> if your config file has not been set in the environment

decrypt private key

openssl rsa -in MYKEY.key >> MYKEY-NOCRYPT.key

generate a certificate siging request for an existing private key

openssl req -out MYCSR.csr -key MYKEY.key -new

generate a certificate signing request based on an existing x509 certificate

openssl x509 -x509toreq -in MYCRT.crt -out MYCSR.csr -signkey MYKEY.key

create self-signed certificate (can be used to sign other certificates)

openssl req -x509 -new -out MYCERT.crt -keyout MYKEY.key -days 365

sign a Certificate Signing Request

openssl x509 -req -in MYCSR.csr -CA MY-CA-CERT.crt -CAkey MY-CA-KEY.key -CAcreateserial -out MYCERT.crt -days 365

-days has to be less than the validity of the CA certificate

---

convert DER (.crt .cer .der) to PEM

openssl x509 -inform der -in MYCERT.cer -out MYCERT.pem

convert PEM to DER

openssl x509 -outform der -in MYCERT.pem -out MYCERT.der

convert PKCS#12 (.pfx .p12) to PEM containing both private key and certificates

openssl pkcs12 -in KEYSTORE.pfx -out KEYSTORE.pem -nodes

add -nocerts for private key only; add -nokeys for certificates only

convert (add) a seperate key and certificate to a new keystore of type PKCS#12

openssl pkcs12 -export -in MYCERT.crt -inkey MYKEY.key -out KEYSTORE.p12 -name "tomcat"

convert (add) a seperate key and certificate to a new keystore of type PKCS#12 for use with a server that should send the chain too (eg Tomcat)

openssl pkcs12 -export -in MYCERT.crt -inkey MYKEY.key -out KEYSTORE.p12 -name "tomcat" -CAfile MY-CA-CERT.crt -caname myCA -chain

you can repeat the combination of "-CAfile" and "-caname" for each intermediate certificate

---

check a private key

openssl rsa -in MYKEY.key -check

add -noout to not disclose the key

check a Certificate Signing Request

openssl req -text -noout -verify -in MYCSR.csr

check a certificate

openssl x509 -in MYCERT.crt -text -noout

check a PKCS#12 keystore

openssl pkcs12 -info -in KEYSTORE.p12

check a trust chain of a certificate

openssl verify -CAfile MYCHAINFILE.pem -verbose MYCERT.crt

trust chain is in directory (hash format): replace -CAfile with -CApath /path/to/CAchainDir/
to check for server usage: -purpose sslserver
to check for client usage: -purpose sslient

---

debug an SSL connection [server doesn't require certificate authentication]

openssl s_client -connect idp.example.be:443

debug an SSL connection with mutual certificate authentication

openssl s_client -connect idp.example.be:8443 -CAfile MY-CA-CERT.crt -cert MYCERT.crt -key MYKEY.key

trust chain is in directory (hash format): replace -CAfile with -CApath /path/to/CAchainDir/
send the starttls command (smtp or pop3 style): -starttls smtp or -starttls pop3

---

keytool

keytool does not support management of private keys inside a keystore. You need to use another tool for that. If you are using the JKS format, that means you need another java-based tool. extkeytool from the Shibboleth distribution can do this.

Create an empty keystore

keytool -genkey -alias foo -keystore truststore.jks
keytool -delete -alias foo -keystore truststore.jks

Generate a private key and an initial certificate as a JKS keystore

keytool -genkey -keyalg RSA -alias "selfsigned" -keystore KEYSTORE.jks -storepass "secret" -validity 360

you can also pass the data for the DN of the certificate as command-line parameters: -dname "CN=${pki-cn}, OU=${pki-ou}, O=${pki-o}, L=${pki-l}, S=${pki-s}, C=${pki-c}"

Generate a secret key that can be used for symmetric encryption. For this to work, you need to make use of a JCEKS keystore.

keytool -genseckey -alias "secret_key" -keystore KEYSTORE.jks -storepass "secret" -storetype "JCEKS"

Generate a Certificate Signing Request for a key in a JKS keystore

keytool -certreq -v -alias "selfsigned" -keystore KEYSTORE.jks -storepass "secret" -file MYCSR.csr

Import a (signed) certificate into a JKS keystore

keytool -import -keystore KEYSTORE.jks -storepass "secret" -file MYCERT.crt

add a public certificate to a JKS keystore, eg the JVM truststore

keytool -import -trustcacerts -alias "sensible-name-for-ca" -file CAcert.crt -keystore MYSTORE.jks

If the JVM truststore contains your certificate or the certificate of the root CA that signed your certificate, then the JVM will trust and thus might accept your certificate. The default truststore already contains the root certificates of most commonly used sommercial CA's. Use this command to add another certificate for trust:

keytool -import -trustcacerts -alias "sensible-name-for-ca" -file CAcert.crt -keystore $JAVA_HOME/lib/security/cacerts

the default password of the Java truststore is "changeit".
if $JAVA_HOME is set to the root of the JDK, then the truststore is it $JAVA_HOME/jre/lib/security/cacerts
keytool does NOT support adding trust certificates to a PKCS12 keystore (which is very unfortunate but probably a good move to promote JKS)

delete a public certificate from a JAVA keystore (JKS; eg JVM truststore)

keytool -delete -alias "sensible-name-for-ca" -keystore $JAVA_HOME/lib/security/cacerts

the default password of the Java truststore is "changeit".
if $JAVA_HOME is set to the root of the JDK, then the truststore is it $JAVA_HOME/jre/lib/security/cacerts

List the certificates inside a keystore

keytool -list -v -keystore KEYSTORE.jks

-storetype pkcs12 can be used

Get information about a stand-alone certificate

keytool -printcert -v -file MYCERT.crt

notes:

openssl for win32 can be downloaded at http://www.slproweb.com/products/Win32OpenSSL.html. Version v0.9.8 is known to cause problems in combination with Shibboleth SP v1.3!

keytool is a part of each Sun Java distribution (binary). You need it to manipulate the Java KeyStore (JKS) format.

hash format: the -CApath directory should contain each certificate that needs to be trusted. The name of each certificate has to be its hashed value and a number. When running unix, execute "$ c_rehash ./" to create symlinks with the correct names. You can also do this manually with the -hash option of openssl (see "openssl verify").

please send remarks, corrections and other often used commands to shib@kuleuven.net