Tools to generate, test and play around with SSL keys, certificates and chains

ca_gen.sh

#!/usr/bin/env bash

# Generate the root CA certificate
# Generate a self signed certificate for the CA along with a key.
mkdir -p ca/private
mkdir -p ca/newcerts
chmod 700 ca/private
# NOTE: I'm using -nodes, this means that once anybody gets
# their hands on this particular certificate they can become this CA.
openssl req \
    -x509 \
    -nodes \
    -days 3650 \
    -newkey rsa:4096 \
    -keyout ca/private/ca_key.pem \
    -out ca/ca_cert.pem \
    -subj "/C=US/ST=Acme State/L=Acme City/O=Acme Inc./CN=example.com"
# Generate Serial file (some random number)
echo "53507182330129322352" > ca/serial
# Generate index file
touch ca/index.txt

my_ssl.cnf

# NOTE: This is just a minimally modified OpenSSL conf file.
# SHOULD NOT BE USED IN PRODUCTION at any cost.
#
# OpenSSL example configuration file.
# This is mostly being used for generation of certificate requests.
#

# This definition stops the following lines choking if HOME isn't
# defined.
HOME            = .
RANDFILE        = $ENV::HOME/.rnd

# Extra OBJECT IDENTIFIER info:
#oid_file       = $ENV::HOME/.oid
oid_section     = new_oids

# To use this configuration file with the "-extfile" option of the
# "openssl x509" utility, name here the section containing the
# X.509v3 extensions to use:
# extensions        = 
# (Alternatively, use a configuration file that has only
# X.509v3 extensions in its main [= default] section.)

[ new_oids ]

# We can add new OIDs in here for use by 'ca', 'req' and 'ts'.
# Add a simple OID like this:
# testoid1=1.2.3.4
# Or use config file substitution like this:
# testoid2=${testoid1}.5.6

# Policies used by the TSA examples.
tsa_policy1 = 1.2.3.4.1
tsa_policy2 = 1.2.3.4.5.6
tsa_policy3 = 1.2.3.4.5.7

####################################################################
[ ca ]
default_ca  = CA_default        # The default ca section

####################################################################
[ CA_default ]

dir         = ./ca       # Where everything is kept
certs       = $dir/certs        # Where the issued certs are kept
crl_dir     = $dir/crl      # Where the issued crl are kept
database    = $dir/index.txt    # database index file.
#unique_subject = no            # Set to 'no' to allow creation of
                    # several ctificates with same subject.
new_certs_dir   = $dir/newcerts     # default place for new certs.

certificate = $dir/ca_cert.pem  # The CA certificate
serial      = $dir/serial       # The current serial number
crlnumber   = $dir/crlnumber    # the current crl number
                    # must be commented out to leave a V1 CRL
crl     = $dir/crl.pem      # The current CRL
private_key = $dir/private/ca_key.pem # The private key
RANDFILE    = $dir/private/.rand    # private random number file

x509_extensions = usr_cert      # The extentions to add to the cert

# Comment out the following two lines for the "traditional"
# (and highly broken) format.
name_opt    = ca_default        # Subject Name options
cert_opt    = ca_default        # Certificate field options

# Extension copying option: use with caution.
# copy_extensions = copy

# Extensions to add to a CRL. Note: Netscape communicator chokes on V2 CRLs
# so this is commented out by default to leave a V1 CRL.
# crlnumber must also be commented out to leave a V1 CRL.
# crl_extensions    = crl_ext

default_days    = 365           # how long to certify for
default_crl_days= 30            # how long before next CRL
default_md  = default       # use public key default MD
preserve    = no            # keep passed DN ordering

# A few difference way of specifying how similar the request should look
# For type CA, the listed attributes must be the same, and the optional
# and supplied fields are just that :-)
policy      = policy_match

# For the CA policy
[ policy_match ]
countryName     = match
stateOrProvinceName = match
organizationName    = match
organizationalUnitName  = optional
commonName      = supplied
emailAddress        = optional

# For the 'anything' policy
# At this point in time, you must list all acceptable 'object'
# types.
[ policy_anything ]
countryName     = optional
stateOrProvinceName = optional
localityName        = optional
organizationName    = optional
organizationalUnitName  = optional
commonName      = supplied
emailAddress        = optional

####################################################################
[ req ]
default_bits        = 2048
default_keyfile     = privkey.pem
distinguished_name  = req_distinguished_name
attributes      = req_attributes
x509_extensions = v3_ca # The extentions to add to the self signed cert

# Passwords for private keys if not present they will be prompted for
# input_password = secret
# output_password = secret

# This sets a mask for permitted string types. There are several options. 
# default: PrintableString, T61String, BMPString.
# pkix   : PrintableString, BMPString (PKIX recommendation before 2004)
# utf8only: only UTF8Strings (PKIX recommendation after 2004).
# nombstr : PrintableString, T61String (no BMPStrings or UTF8Strings).
# MASK:XXXX a literal mask value.
# WARNING: ancient versions of Netscape crash on BMPStrings or UTF8Strings.
string_mask = utf8only

# req_extensions = v3_req # The extensions to add to a certificate request

[ req_distinguished_name ]
countryName         = Country Name (2 letter code)
countryName_default     = AU
countryName_min         = 2
countryName_max         = 2

stateOrProvinceName     = State or Province Name (full name)
stateOrProvinceName_default = Some-State

localityName            = Locality Name (eg, city)

0.organizationName      = Organization Name (eg, company)
0.organizationName_default  = Internet Widgits Pty Ltd

# we can do this but it is not needed normally :-)
#1.organizationName     = Second Organization Name (eg, company)
#1.organizationName_default = World Wide Web Pty Ltd

organizationalUnitName      = Organizational Unit Name (eg, section)
#organizationalUnitName_default =

commonName          = Common Name (e.g. server FQDN or YOUR name)
commonName_max          = 64

emailAddress            = Email Address
emailAddress_max        = 64

# SET-ex3           = SET extension number 3

[ req_attributes ]
challengePassword       = A challenge password
challengePassword_min       = 4
challengePassword_max       = 20

unstructuredName        = An optional company name

[ usr_cert ]

# These extensions are added when 'ca' signs a request.

# This goes against PKIX guidelines but some CAs do it and some software
# requires this to avoid interpreting an end user certificate as a CA.

basicConstraints=CA:FALSE

# Here are some examples of the usage of nsCertType. If it is omitted
# the certificate can be used for anything *except* object signing.

# This is OK for an SSL server.
# nsCertType            = server

# For an object signing certificate this would be used.
# nsCertType = objsign

# For normal client use this is typical
# nsCertType = client, email

# and for everything including object signing:
# nsCertType = client, email, objsign

# This is typical in keyUsage for a client certificate.
# keyUsage = nonRepudiation, digitalSignature, keyEncipherment

# This will be displayed in Netscape's comment listbox.
nsComment           = "OpenSSL Generated Certificate"

# PKIX recommendations harmless if included in all certificates.
subjectKeyIdentifier=hash
authorityKeyIdentifier=keyid,issuer

# This stuff is for subjectAltName and issuerAltname.
# Import the email address.
# subjectAltName=email:copy
# An alternative to produce certificates that aren't
# deprecated according to PKIX.
# subjectAltName=email:move

# Copy subject details
# issuerAltName=issuer:copy

#nsCaRevocationUrl      = http://www.domain.dom/ca-crl.pem
#nsBaseUrl
#nsRevocationUrl
#nsRenewalUrl
#nsCaPolicyUrl
#nsSslServerName

# This is required for TSA certificates.
# extendedKeyUsage = critical,timeStamping

[ v3_req ]

# Extensions to add to a certificate request

basicConstraints = CA:FALSE
keyUsage = nonRepudiation, digitalSignature, keyEncipherment

[ v3_ca ]


# Extensions for a typical CA


# PKIX recommendation.

subjectKeyIdentifier=hash

authorityKeyIdentifier=keyid:always,issuer

# This is what PKIX recommends but some broken software chokes on critical
# extensions.
#basicConstraints = critical,CA:true
# So we do this instead.
basicConstraints = CA:true

# Key usage: this is typical for a CA certificate. However since it will
# prevent it being used as an test self-signed certificate it is best
# left out by default.
# keyUsage = cRLSign, keyCertSign

# Some might want this also
# nsCertType = sslCA, emailCA

# Include email address in subject alt name: another PKIX recommendation
# subjectAltName=email:copy
# Copy issuer details
# issuerAltName=issuer:copy

# DER hex encoding of an extension: beware experts only!
# obj=DER:02:03
# Where 'obj' is a standard or added object
# You can even override a supported extension:
# basicConstraints= critical, DER:30:03:01:01:FF

[ crl_ext ]

# CRL extensions.
# Only issuerAltName and authorityKeyIdentifier make any sense in a CRL.

# issuerAltName=issuer:copy
authorityKeyIdentifier=keyid:always

[ proxy_cert_ext ]
# These extensions should be added when creating a proxy certificate

# This goes against PKIX guidelines but some CAs do it and some software
# requires this to avoid interpreting an end user certificate as a CA.

basicConstraints=CA:FALSE

# Here are some examples of the usage of nsCertType. If it is omitted
# the certificate can be used for anything *except* object signing.

# This is OK for an SSL server.
# nsCertType            = server

# For an object signing certificate this would be used.
# nsCertType = objsign

# For normal client use this is typical
# nsCertType = client, email

# and for everything including object signing:
# nsCertType = client, email, objsign

# This is typical in keyUsage for a client certificate.
# keyUsage = nonRepudiation, digitalSignature, keyEncipherment

# This will be displayed in Netscape's comment listbox.
nsComment           = "OpenSSL Generated Certificate"

# PKIX recommendations harmless if included in all certificates.
subjectKeyIdentifier=hash
authorityKeyIdentifier=keyid,issuer

# This stuff is for subjectAltName and issuerAltname.
# Import the email address.
# subjectAltName=email:copy
# An alternative to produce certificates that aren't
# deprecated according to PKIX.
# subjectAltName=email:move

# Copy subject details
# issuerAltName=issuer:copy

#nsCaRevocationUrl      = http://www.domain.dom/ca-crl.pem
#nsBaseUrl
#nsRevocationUrl
#nsRenewalUrl
#nsCaPolicyUrl
#nsSslServerName

# This really needs to be in place for it to be a proxy certificate.
proxyCertInfo=critical,language:id-ppl-anyLanguage,pathlen:3,policy:foo

####################################################################
[ tsa ]

default_tsa = tsa_config1   # the default TSA section

[ tsa_config1 ]

# These are used by the TSA reply generation only.
dir     = ./demoCA      # TSA root directory
serial      = $dir/tsaserial    # The current serial number (mandatory)
crypto_device   = builtin       # OpenSSL engine to use for signing
signer_cert = $dir/tsacert.pem  # The TSA signing certificate
                    # (optional)
certs       = $dir/cacert.pem   # Certificate chain to include in reply
                    # (optional)
signer_key  = $dir/private/tsakey.pem # The TSA private key (optional)

default_policy  = tsa_policy1       # Policy if request did not specify it
                    # (optional)
other_policies  = tsa_policy2, tsa_policy3  # acceptable policies (optional)
digests     = md5, sha1     # Acceptable message digests (mandatory)
accuracy    = secs:1, millisecs:500, microsecs:100  # (optional)
clock_precision_digits  = 0 # number of digits after dot. (optional)
ordering        = yes   # Is ordering defined for timestamps?
                # (optional, default: no)
tsa_name        = yes   # Must the TSA name be included in the reply?
                # (optional, default: no)
ess_cert_id_chain   = no    # Must the ESS cert id chain be included?
                # (optional, default: no)

ssl_gen.sh

#!/usr/bin/env bash

# Generate a SSL key-cert pair.
#
# Usage: ./ssl_gen.sh <name> <ca_name> [ca]
#    name: Name prefix for the certficate
#    ca_name: Folder where we can find the root/intermediate CA
#               generated by ca_gen.sh or this script.
#    ca: Specifies that this generated key-pair will
#               will be used as an intermediate CA
#               if left blank, then we won't get an intermediate CA

name=$1
ca_name=$2

if [ "$3" == "ca" ]
then
    ca_str="-extensions v3_ca"
else
    ca_str=""
fi

mkdir -p ${name}/private

chmod 700 ${name}/private

openssl genrsa -out ${name}/private/${name}_key.pem 4096

openssl req -new \
    -key ${name}/private/${name}_key.pem \
    -out ${name}/${name}.csr \
    -subj "/C=US/ST=Acme State/L=Acme City/O=Acme Inc./CN=${name}"

openssl ca \
    -config my_ssl.cnf \
    ${ca_str} \
    -days 3650 \
    -batch\
    -cert ${ca_name}/${ca_name}_cert.pem \
    -keyfile ${ca_name}/private/${ca_name}_key.pem \
    -in ${name}/${name}.csr     \
    -out ${name}/${name}_cert.pem

test_ssl.py

#!/usr/bin/env python

import optparse
import os
import socket
import ssl
import sys

SERVER = ("127.0.0.1", 39898)
MAX_MSG_SIZE = 1024


def do_ssl_server(key_file, cert_file, ca_file):
    try:
        # Start listening on some port
        lis_sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
        lis_sock.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
        lis_sock.bind(SERVER)
        lis_sock.listen(socket.SOMAXCONN)
        print "Listening: " + str(SERVER)
        # Accept an SSL connection
        net_sock, cli_addr = lis_sock.accept()
        print "New TCP connection with %s:%d" % cli_addr
        ssl_sock = ssl.wrap_socket(net_sock,
                                   server_side=True,
                                   keyfile=key_file,
                                   certfile=cert_file,
                                   ca_certs=ca_file,
                                   cert_reqs=ssl.CERT_REQUIRED)
        print "Successful SSL connection with %s:%d" % cli_addr
        # Read some data
        data = ssl_sock.read(MAX_MSG_SIZE)
        print "Data: " + str(data)
        # Close sockets
        ssl_sock.close()
        lis_sock.close()
        print "Success"
    except socket.error as err:
        print "Socket Error: " + str(err)
        sys.exit(1)


def do_ssl_client(key_file, cert_file, ca_file):
    try:
        tcp_sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
        ssl_sock = ssl.wrap_socket(tcp_sock,
                server_side=False,
                keyfile=key_file,
                certfile=cert_file,
                ca_certs=ca_file,
                cert_reqs=ssl.CERT_REQUIRED)
        ssl_sock.connect(SERVER)
        ssl_sock.send("Hello, World!\n")
        ssl_sock.close()
        print "Success"
    except socket.error as err:
        print "Socket Error: " + str(err)
        exit(1)


def usage():
    print os.path.basename(__file__) + " <client|server> " + \
            "-k <key_file> -c <cert_file> -x <ca_file>\n"


if __name__ == "__main__":
    parser = optparse.OptionParser()
    parser.add_option("-k", "--key_file", dest="key_file", help="Key File")
    parser.add_option("-c", "--cert_file", dest="cert_file", help="Cert File")
    parser.add_option("-x", "--ca_file", dest="ca_file", help="CA File")
    cmd_ops, args = parser.parse_args()
    # Sanity checks
    if len(args) != 1:
        usage()
        print "Invalid number of commands"
        sys.exit(1)
    if cmd_ops.key_file is None:
        usage()
        print "Key file is missing"
        sys.exit(1)
    if cmd_ops.cert_file is None:
        usage()
        print "Cert file is missing"
        sys.exit(1)
    if cmd_ops.ca_file is None:
        usage()
        print "CA file is missing"
        sys.exit(1)
    # Now do either server or client action
    if args[0] == "server":
        do_ssl_server(key_file=cmd_ops.key_file,
                cert_file=cmd_ops.cert_file,
                ca_file=cmd_ops.ca_file)
    elif args[0] == "client":
        do_ssl_client(key_file=cmd_ops.key_file,
                cert_file=cmd_ops.cert_file,
                ca_file=cmd_ops.ca_file)
    else:
        usage()
        print "Invalid command: " + str(args[0])
        sys.exit(1)
    # Done
    sys.exit(0)