Various Types of OpenSSL Commands and Keytool

OpenSSL Commands and SSL Keytool List

OpenSSL is an open-source implementation of SSL/TLS protocols and is considered to be one of the most versatile SSL tools. It’s a library written in C programming language that implements the basic cryptographic functions. OpenSSL has different versions for most Unix-like operating systems, which include Mac OC X, Linux, and Microsoft Windows etc.

Open SSL is normally used to generate a Certificate Signing Request (CSR) and private key for different platforms. However, it also has several different functions, which can be listed as follows. It is used to:

• View details about a CSR or a certificate
• Compare MD5 hash of a certificate and private key to ensure they match
• Verify proper installation of the certificate on a website
• Convert the certificate format

Most of the functions mentioned below can also be performed without involving OpenSSL by using these convenient SSL tools. Here, we have put together few of the most common OpenSSL commands.

General OpenSSL Commands

These are the set of commands that allow the users to generate CSRs, Certificates, Private Keys and many other miscellaneous tasks. Here, we have listed few such commands:

(1) Generate a Certificate Signing Request (CSR) and new private key

openssl req -out CSR.csr -new -newkey rsa:2048 -nodes -keyout privateKey.key

 

(2) Generate a self-signed certificate

openssl req -x509 -nodes -days 365 -newkey rsa:2048 -keyout privateKey.key -out certificate.crt

 

(3) Create CSR based on an existing private key

openssl req -out CSR.csr -key privateKey.key –new

 

(4) Create CSR based on an existing certificate

openssl x509 -x509toreq -in certificate.crt -out CSR.csr -signkey privateKey.key

 

(5) Passphrase removal from a private key

openssl rsa -in privateKey.pem -out newPrivateKey.pem

 

SSL Check Commands

These commands are very helpful if the user wants to check the information within an SSL certificate, a Private Key, and CSR. Few online tools can also help you check CSRs and check SSL certificates.

(1) Certificate Signing Request (CSR)

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

 

(2) Private Key

openssl rsa -in privateKey.key –check

 

(3) SSL Certificate

openssl x509 -in certificate.crt -text –noout

 

(4) PKCS#12 File (.pfx or .p12)

openssl pkcs12 -info -in keyStore.p12

 

Convert Commands

As per the title, these commands help convert the certificates and keys into different formats to impart them the compatibility with specific servers types. For example, a PEM file, compatible with Apache server, can be converted to PFX (PKCS#12), after which it would be possible for it to work with Tomcat or IIS. However, you can also use the SSL Converter to change the format, without having to involve OpenSSL.

(1) Convert DER Files (.crt, .cer, .der) to PEM

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

 

(2) Convert PEM to DER

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

 

(3) Convert PKCS #12 File (.pfx, .p12) Containing a Private Key and Certificate to PEM

openssl pkcs12 -in keyStore.pfx -out keyStore.pem –nodes

To output only the private key, users can add –nocerts or –nokeys to output only the certificates.

 

(4) Convert PEM Certificate (File and a Private Key) to PKCS # 12 (.pfx #12)

openssl pkcs12 -export -out certificate.pfx -inkey privateKey.key -in certificate.crt -certfile CACert.crt

 

Debugging Using OpenSSL Commands

If there are error messages popping up about your private key not matching the certificate or that the newly-installed certificate is not trusted, you can rely on one of the comments mentioned below. You can also use the SSL certificate checker tool for verifying the correct installation of an SSL certificate.

(1) Check SSL Connection (All certificates, including Intermediates, are to be displayed)

Here, all the certificates should be displayed, including the Intermediates as well.

openssl s_client -connect www.paypal.com:443

 

(2) Check MD5 Hash of Public Key

This is to ensure that the public key matches with the CSR or the private key.

openssl x509 -noout -modulus -in certificate.crt | openssl md5
openssl rsa -noout -modulus -in privateKey.key | openssl md5
openssl req -noout -modulus -in CSR.csr | openssl md5

 

SSL Keytool List

Java Keytool is a key and certificate management utility that allows the users to cache the certificate and manage their own private or public key pairs and certificates. Java Keytool stores all the keys and certificates in a ‘Keystore’, which is, by default, implemented as a file. It contains private keys and certificates that are essential for establishing the reliability of the primary certificate and completing a chain of trust.

Every certificate in Java Keystore has a unique pseudonym/alias. For creating a ‘Java Keystore’, you need to first create the .jks file containing only the private key in the beginning. After that, you need to generate a Certificate Signing Request (CSR) and generate a certificate from it. After this, import the certificate to the Keystore including any root certificates.

The ‘Java Keytool’ basically contains several other functions that help the users export a certificate or to view the certificate details or the list of certificates in Keystore.

Here are few important Java Keytool commands:

 

For Creating and Importing

These Keytool commands allow users to create a new Java Keytool keysKeystore, generate a Certificate Signing Request (CSR) and import certificates. Before you import the primary certificate for your domain, you need to first import any root or intermediate certificates.

(1) Import a root or intermediate CA certificate to an existing Java keystore

keytool -import -trustcacerts -alias root -file Thawte.crt -keystore keystore.jks

 

(2) Import a signed primary certificate to an existing Java keystore

keytool -import -trustcacerts -alias mydomain -file mydomain.crt -keystore keystore.jks

 

(3) Generate a keystore and self-signed certificate

keytool -genkey -keyalg RSA -alias selfsigned -keystore keystore.jks -storepass password -validity 360 -keysize 2048

 

(4) Generate Key Pair & Java Keystore

keytool -genkey -alias mydomain -keyalg RSA -keystore keystore.jks -keysize 2048

 

(5) Generate CSR for existing Java Keystore

keytool -certreq -alias mydomain -keystore keystore.jks -file mydomain.csr

 

For Checking

Users can check the information within a certificate or Java keystore by using the following commands:

(1) Check an individual certificate

keytool -printcert -v -file mydomain.crt

 

(2) Check certificates in Java keystore

keytool -list -v -keystore keystore.jks

 

(3) Check specific keystore entry using an alias

keytool -list -v -keystore keystore.jks -alias mydomain

 

Other Java Keytool Commands

(1) Delete a certificate from Java Keystore keystore

keytool -delete -alias mydomain -keystore keystore.jks

 

(2) Change the password in Java keystore / Change a Java keystore password

keytool -storepasswd -new new_storepass -keystore keystore.jks

 

(3) Export certificate from Java keystore

keytool -export -alias mydomain -file mydomain.crt -keystore keystore.jks

 

(4) List the trusted CA Certificate

keytool -list -v -keystore $JAVA_HOME/jre/lib/security/cacerts

 

(5) Import new CA into Trusted Certs

keytool -import -trustcacerts -file /path/to/ca/ca.pem -alias CA_ALIAS -keystore $JAVA_HOME/jre/lib/security/cacerts

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