As a software developer, especially when working with security or web-based technologies, one is often required to deal with X.509 certificates. Although it is increasingly easy to obtain a certificate issued by a trusted certificate authority, understanding how to create and use them yourself is invaluable. Below is a list of the OpenSSL commands that have been the most useful to me.

Create a new RSA key:

openssl genrsa -out key_filename.key 2048

The genrsa command generates an random RSA private key consisting of two prime numbers. The size of the key in bits is determined by the last argument (2048 above). Larger values are more secure, but use more resources. NIST estimates that key sizes of 2048 bytes will be secure until 2030. Currently it is possible to crack a key of size 1024 in approximately 100 hours.

Create self-signed X.509 certificate:

openssl req \
    -x509 \
    -sha256 \
    -days 9999 \
    -newkey rsa:2048 \
    -keyout key_filename.key \
    -nodes \
    -out ca_filename.cer

The req command with option -x509 generates a self signed X.509 certificate which can be used for testing or as the root certificate of a certificate authority. Certificates generated in this manner are very useful for development but have limited use in production environments. A common use of self signed certificates is to enable HTTPS on a local or non-production web server.

When used in this manner, the req command will prompt for information to be included in the resulting certificate. When prompted for Common Name, provide the fully qualified domain name to be secured (ex. www.google.com). It is also possible to create a wildcard certificate which can be used to secure unlimited sub-domains by using the * character in place of a concrete sub-domain (ex. *.google.com). Note that to secure multiple domains with the same certificate (ex. www.google.com, www.google.org, www.google.net) the Subject Alternate Name (SAN) extention must be used instead. Using the SAN extension is discussed in the example for the x509 command below.

The -days option determines the number of days (relative to the current date) that the certificate will be valid. The -newkey option generates a new CSR and private key using the specified algorithm. If the -keyout option is used the generated key will be output to the specified file. Option -nodes (no DES) indicates that they generated key should be stored without encryption and can be omitted if you wish to protect the key with a pass phrase.

The -sha256 option indicates that the SHA256 hashing algorithm should be used to generate the message digest when digitally signing the certificate. Note that SHA256 is currently the default and this option can usually be omitted. It is important to use a secure digest algorithm because certificates signed with an insecure message digest such as SHA1 generate warnings in some browsers resulting in sites that clients will not consider trustworthy.

Create certificate signing request:

openssl req \
    -new \
    -sha256 \
    -key key_filename.key \
    -out request_filename.csr

The req command with option -new generates a new certificate signing request containing the information needed by a certificate authority to create a new X.509 certificate. This command prompts for the same certificate information as the example above.

The -key option specifies the key file to use. It is also common to generate a new key as part of this command by using for example -newkey rsa:2048 -keyout key_filename.key -nodes instead of -key key_filename.key. This technique eliminates the need for the use of genrsa as shown in the first example above.

Sign CSR to create new X.509 certificate:

openssl x509 \
    -req \
    -sha256 \
    -days 9999 \
    -in request_filename.csr \
    -CA ca_filename.cer \
    -CAkey key_filename.key \
    -CAcreateserial \
    -out certificate_filename.cer

The x509 command with option -req is used to create an X.509 certificate from a certificate signing request. The -CA option specifies the certificate of the signing Certificate Authority and the -CAkey option specifies the private key to use for the digital signature of the resulting certificate. The -CAcreateserial option indicates that a new serial number file should be created if needed and that the serial number of the resulting certificate should be read from this file.

To create a certificate with the Subject Alternate Names extension, add the options -extensions v3_req -extfile san.cnf as shown below.

openssl x509 \
    -req \
    -sha256 \
    -days 9999 \
    -in request_filename.csr \
    -CA ca_filename.cer \
    -CAkey key_filename.key \
    -CAcreateserial \
    -out certificate_filename.cer \
    -extensions v3_req \
    -extfile san.cnf

The file specified by -extfile is used to define the domain names to be secured by the certificate and should be in the following format.

[v3_req]
subjectAltName = @alt_names
[alt_names]
DNS.1 = your.domain.name
DNS.2 = another.domain
...
DNS.x = last.domain.name

For more information about creating certificates with the SAN extension see http://techbrahmana.blogspot.com/2013/10/creating-wildcard-self-signed.html.

Combine X.509 certificate and key into PKCS12 encoding:

openssl pkcs12 \
    -export \
    -out pkcs12_filename.pfx \
    -inkey key_filename.key \
    -in certificate_filename.cer

The pkcs12 command with the -export option can be used to combine a key and certificate into a single file in PKCS12 format secured by a pass phrase. This is useful when working with Microsoft systems where PKCS12 is commonly used. Note that the file extension used for PKCS12 is typically .pfx on Microsoft systems and .p12 on Linux systems.