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[rubygems/rubygems] Add support to build and sign certificates with multiple key algorithms

Browse source 
https://github.com/rubygems/rubygems/commit/967876f15d

Co-Authored-By: Frederik Dudzik <frederik.dudzik@shopify.com>
This commit is contained in:
Jenny Shen 2021-10-06 17:39:23 -04:00 committed by Hiroshi SHIBATA
parent 10fe8495cd
commit 92ec010595
No known key found for this signature in database
GPG key ID: F9CF13417264FAC2
8 changed files with 175 additions and 37 deletions
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19
lib/rubygems/commands/cert_command.rb
View file

@ -43,6 +43,11 @@ class Gem::Commands::CertCommand < Gem::Command
options[:key] = open_private_key(key_file)
end
add_option('-A', '--key-algorithm ALGORITHM',
'Select which key algorithm to use for --build') do |algorithm, options|
options[:key_algorithm] = algorithm
end
add_option('-s', '--sign CERT',
'Signs CERT with the key from -K',
'and the certificate from -C') do |cert_file, options|
@ -89,14 +94,14 @@ class Gem::Commands::CertCommand < Gem::Command
def open_private_key(key_file)
check_openssl
passphrase = ENV['GEM_PRIVATE_KEY_PASSPHRASE']
key = OpenSSL::PKey::RSA.new File.read(key_file), passphrase
key = OpenSSL::PKey.read File.read(key_file), passphrase
raise OptionParser::InvalidArgument,
"#{key_file}: private key not found" unless key.private?
key
rescue Errno::ENOENT
raise OptionParser::InvalidArgument, "#{key_file}: does not exist"
rescue OpenSSL::PKey::RSAError
raise OptionParser::InvalidArgument, "#{key_file}: invalid RSA key"
rescue OpenSSL::PKey::PKeyError, ArgumentError
raise OptionParser::InvalidArgument, "#{key_file}: invalid RSA, DSA, or EC key"
end
def execute
@ -170,7 +175,8 @@ class Gem::Commands::CertCommand < Gem::Command
raise Gem::CommandLineError,
"Passphrase and passphrase confirmation don't match" unless passphrase == passphrase_confirmation
key = Gem::Security.create_key
algorithm = options[:key_algorithm] || Gem::Security::DEFAULT_KEY_ALGORITHM
key = Gem::Security.create_key(algorithm)
key_path = Gem::Security.write key, "gem-private_key.pem", 0600, passphrase
return key, key_path
@ -255,13 +261,14 @@ For further reading on signing gems see `ri Gem::Security`.
key_file = File.join Gem.default_key_path
key = File.read key_file
passphrase = ENV['GEM_PRIVATE_KEY_PASSPHRASE']
options[:key] = OpenSSL::PKey::RSA.new key, passphrase
options[:key] = OpenSSL::PKey.read key, passphrase
rescue Errno::ENOENT
alert_error \
"--private-key not specified and ~/.gem/gem-private_key.pem does not exist"
terminate_interaction 1
rescue OpenSSL::PKey::RSAError
rescue OpenSSL::PKey::PKeyError
alert_error \
"--private-key not specified and ~/.gem/gem-private_key.pem is not valid"

62
lib/rubygems/security.rb
View file

@ -152,6 +152,7 @@ require_relative 'openssl'
# certificate for EMAIL_ADDR
# -C, --certificate CERT Signing certificate for --sign
# -K, --private-key KEY Key for --sign or --build
# -A, --key-algorithm ALGORITHM Select key algorithm for --build from RSA, DSA, or EC. Defaults to RSA.
# -s, --sign CERT Signs CERT with the key from -K
# and the certificate from -C
# -d, --days NUMBER_OF_DAYS Days before the certificate expires
@ -317,7 +318,6 @@ require_relative 'openssl'
# * Honor extension restrictions
# * Might be better to store the certificate chain as a PKCS#7 or PKCS#12
# file, instead of an array embedded in the metadata.
# * Flexible signature and key algorithms, not hard-coded to RSA and SHA1.
#
# == Original author
#
@ -337,17 +337,19 @@ module Gem::Security
DIGEST_NAME = 'SHA256' # :nodoc:
##
# Algorithm for creating the key pair used to sign gems
# Length of keys created by RSA and DSA keys
KEY_ALGORITHM =
if defined?(OpenSSL::PKey::RSA)
OpenSSL::PKey::RSA
end
RSA_DSA_KEY_LENGTH = 3072
##
# Length of keys created by KEY_ALGORITHM
# Default algorithm to use when building a key pair
KEY_LENGTH = 3072
DEFAULT_KEY_ALGORITHM = 'RSA'
##
# Named curve used for Elliptic Curve
EC_NAME = 'secp384r1'
##
# Cipher used to encrypt the key pair used to sign gems.
@ -400,7 +402,7 @@ module Gem::Security
serial = 1)
cert = OpenSSL::X509::Certificate.new
cert.public_key = key.public_key
cert.public_key = get_public_key(key)
cert.version = 2
cert.serial = serial
@ -418,6 +420,24 @@ module Gem::Security
cert
end
##
# Gets the right public key from a PKey instance
def self.get_public_key(key)
return key.public_key unless key.is_a?(OpenSSL::PKey::EC)
ec_key = OpenSSL::PKey::EC.new(key.group.curve_name)
ec_key.public_key = key.public_key
ec_key
end
##
# In Ruby 2.3 EC doesn't implement the private_key? but not the private? method
if defined?(OpenSSL::PKey::EC) && Gem::Version.new(String.new(RUBY_VERSION)) < Gem::Version.new("2.4.0")
OpenSSL::PKey::EC.send(:alias_method, :private?, :private_key?)
end
##
# Creates a self-signed certificate with an issuer and subject from +email+,
# a subject alternative name of +email+ and the given +extensions+ for the
@ -459,11 +479,25 @@ module Gem::Security
end
##
# Creates a new key pair of the specified +length+ and +algorithm+. The
# default is a 3072 bit RSA key.
# Creates a new key pair of the specified +algorithm+. RSA, DSA, and EC
# are supported.
def self.create_key(length = KEY_LENGTH, algorithm = KEY_ALGORITHM)
algorithm.new length
def self.create_key(algorithm)
if defined?(OpenSSL::PKey)
case algorithm.downcase
when 'dsa'
OpenSSL::PKey::DSA.new(RSA_DSA_KEY_LENGTH)
when 'rsa'
OpenSSL::PKey::RSA.new(RSA_DSA_KEY_LENGTH)
when 'ec'
domain_key = OpenSSL::PKey::EC.new(EC_NAME)
domain_key.generate_key
domain_key
else
raise Gem::Security::Exception,
"#{algorithm} algorithm not found. RSA, DSA, and EC algorithms are supported."
end
end
end
##
@ -492,7 +526,7 @@ module Gem::Security
raise Gem::Security::Exception,
"incorrect signing key for re-signing " +
"#{expired_certificate.subject}" unless
expired_certificate.public_key.to_pem == private_key.public_key.to_pem
expired_certificate.public_key.to_pem == get_public_key(private_key).to_pem
unless expired_certificate.subject.to_s ==
expired_certificate.issuer.to_s

8
lib/rubygems/security/policy.rb
View file

@ -115,9 +115,11 @@ class Gem::Security::Policy
raise Gem::Security::Exception, 'missing key or signature'
end
public_key = Gem::Security.get_public_key(key)
raise Gem::Security::Exception,
"certificate #{signer.subject} does not match the signing key" unless
signer.public_key.to_pem == key.public_key.to_pem
signer.public_key.to_pem == public_key.to_pem
true
end
@ -164,9 +166,9 @@ class Gem::Security::Policy
end
save_cert = OpenSSL::X509::Certificate.new File.read path
save_dgst = digester.digest save_cert.public_key.to_s
save_dgst = digester.digest save_cert.public_key.to_pem
pkey_str = root.public_key.to_s
pkey_str = root.public_key.to_pem
cert_dgst = digester.digest pkey_str
raise Gem::Security::Exception,

7
lib/rubygems/security/signer.rb
View file

@ -83,8 +83,8 @@ class Gem::Security::Signer
@digest_name = Gem::Security::DIGEST_NAME
@digest_algorithm = Gem::Security.create_digest(@digest_name)
if @key && !@key.is_a?(OpenSSL::PKey::RSA)
@key = OpenSSL::PKey::RSA.new(File.read(@key), @passphrase)
if @key && !@key.is_a?(OpenSSL::PKey::PKey)
@key = OpenSSL::PKey.read(File.read(@key), @passphrase)
end
if @cert_chain
@ -177,8 +177,7 @@ class Gem::Security::Signer
disk_cert = File.read(disk_cert_path) rescue nil
disk_key_path = File.join(Gem.default_key_path)
disk_key =
OpenSSL::PKey::RSA.new(File.read(disk_key_path), @passphrase) rescue nil
disk_key = OpenSSL::PKey.read(File.read(disk_key_path), @passphrase) rescue nil
return unless disk_key

4
test/rubygems/helper.rb
View file

@ -1519,14 +1519,14 @@ Also, a list:
end
##
# Loads an RSA private key named +key_name+ with +passphrase+ in <tt>test/rubygems/</tt>
# Loads a private key named +key_name+ with +passphrase+ in <tt>test/rubygems/</tt>
def self.load_key(key_name, passphrase = nil)
key_file = key_path key_name
key = File.read key_file
OpenSSL::PKey::RSA.new key, passphrase
OpenSSL::PKey.read key, passphrase
end
##

9
test/rubygems/private_ec_key.pem Normal file
View file

@ -0,0 +1,9 @@
-----BEGIN EC PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,4107F98A374CB8EC18F1AA4EA4B6A0DB
BRklFxJGcz7gqQYxek8TZkt8qbPhB0FSR6nyw3SYuio/2tlT9ohs74mlK3EbG9Lt
Y4OquJbksBFmoB7fIoM4vnuIZ0Eoz2ooxn9tjhBtqJ3mVscYXwZmA3UDUWDMlviQ
Fu37OpikQv4TFA1jlmUK0LM8xmUCfUeLl0kHD17lFsz2gkO2kwg8mn/YUMOIaDOu
EnnmxbAwnZBpemQkQfpTt2mYL9gu3CcMt5gokBuGDxY=
-----END EC PRIVATE KEY-----

67
test/rubygems/test_gem_commands_cert_command.rb
View file

@ -14,9 +14,10 @@ class TestGemCommandsCertCommand < Gem::TestCase
ALTERNATE_CERT = load_cert 'alternate'
EXPIRED_PUBLIC_CERT = load_cert 'expired'
ALTERNATE_KEY_FILE = key_path 'alternate'
PRIVATE_KEY_FILE = key_path 'private'
PUBLIC_KEY_FILE = key_path 'public'
ALTERNATE_KEY_FILE = key_path 'alternate'
PRIVATE_KEY_FILE = key_path 'private'
PRIVATE_EC_KEY_FILE = key_path 'private_ec'
PUBLIC_KEY_FILE = key_path 'public'
ALTERNATE_CERT_FILE = cert_path 'alternate'
CHILD_CERT_FILE = cert_path 'child'
@ -142,6 +143,42 @@ Added '/CN=alternate/DC=example'
assert_path_exist File.join(@tempdir, 'gem-public_cert.pem')
end
def test_execute_build_key_algorithm_ec_key
passphrase = 'Foo bar'
@cmd.handle_options %W[--build nobody@example.com --key-algorithm ec]
@build_ui = Gem::MockGemUi.new "#{passphrase}\n#{passphrase}"
use_ui @build_ui do
@cmd.execute
end
output = @build_ui.output.squeeze("\n").split "\n"
assert_equal "Passphrase for your Private Key: ",
output.shift
assert_equal "Please repeat the passphrase for your Private Key: ",
output.shift
assert_equal "Certificate: #{File.join @tempdir, 'gem-public_cert.pem'}",
output.shift
assert_equal "Private Key: #{File.join @tempdir, 'gem-private_key.pem'}",
output.shift
assert_equal "Don't forget to move the key file to somewhere private!",
output.shift
assert_empty output
assert_empty @build_ui.error
assert_path_exist File.join(@tempdir, 'gem-private_key.pem')
cert_path = File.join(@tempdir, 'gem-public_cert.pem')
assert_path_exist cert_path
cert = OpenSSL::X509::Certificate.new(File.read(cert_path))
assert cert.public_key.is_a? OpenSSL::PKey::EC
end
def test_execute_build_bad_email_address
passphrase = 'Foo bar'
email = "nobody@"
@ -279,6 +316,28 @@ Added '/CN=alternate/DC=example'
assert_path_exist File.join(@tempdir, 'gem-public_cert.pem')
end
def test_execute_build_ec_key
@cmd.handle_options %W[
--build nobody@example.com
--private-key #{PRIVATE_EC_KEY_FILE}
]
use_ui @ui do
@cmd.execute
end
output = @ui.output.split "\n"
assert_equal "Certificate: #{File.join @tempdir, 'gem-public_cert.pem'}",
output.shift
assert_empty output
assert_empty @ui.error
assert_path_exist File.join(@tempdir, 'gem-public_cert.pem')
assert_path_not_exist File.join(@tempdir, 'gem-private_key.pem')
end
def test_execute_certificate
use_ui @ui do
@cmd.handle_options %W[--certificate #{PUBLIC_CERT_FILE}]
@ -742,7 +801,7 @@ ERROR: --private-key not specified and ~/.gem/gem-private_key.pem does not exis
@cmd.handle_options %W[--private-key #{bad}]
end
assert_equal "invalid argument: --private-key #{bad}: invalid RSA key",
assert_equal "invalid argument: --private-key #{bad}: invalid RSA, DSA, or EC key",
e.message
e = assert_raise OptionParser::InvalidArgument do

36
test/rubygems/test_gem_security.rb
View file

@ -12,6 +12,7 @@ end
class TestGemSecurity < Gem::TestCase
CHILD_KEY = load_key 'child'
EC_KEY = load_key 'private_ec', 'Foo bar'
ALTERNATE_CERT = load_cert 'child'
CHILD_CERT = load_cert 'child'
@ -103,11 +104,38 @@ class TestGemSecurity < Gem::TestCase
end
def test_class_create_key
key = @SEC.create_key 1024
key = @SEC.create_key 'rsa'
assert_kind_of OpenSSL::PKey::RSA, key
end
def test_class_create_key_downcases
key = @SEC.create_key 'DSA'
assert_kind_of OpenSSL::PKey::DSA, key
end
def test_class_create_key_raises_unknown_algorithm
e = assert_raise Gem::Security::Exception do
@SEC.create_key 'NOT_RSA'
end
assert_equal "NOT_RSA algorithm not found. RSA, DSA, and EC algorithms are supported.",
e.message
end
def test_class_get_public_key_rsa
pkey_pem = PRIVATE_KEY.public_key.to_pem
assert_equal pkey_pem, @SEC.get_public_key(PRIVATE_KEY).to_pem
end
def test_class_get_public_key_ec
pkey = @SEC.get_public_key(EC_KEY)
assert_respond_to pkey, :to_pem
end
def test_class_email_to_name
assert_equal '/CN=nobody/DC=example',
@SEC.email_to_name('nobody@example').to_s
@ -259,7 +287,7 @@ class TestGemSecurity < Gem::TestCase
end
def test_class_write
key = @SEC.create_key 1024
key = @SEC.create_key 'rsa'
path = File.join @tempdir, 'test-private_key.pem'
@ -273,7 +301,7 @@ class TestGemSecurity < Gem::TestCase
end
def test_class_write_encrypted
key = @SEC.create_key 1024
key = @SEC.create_key 'rsa'
path = File.join @tempdir, 'test-private_encrypted_key.pem'
@ -289,7 +317,7 @@ class TestGemSecurity < Gem::TestCase
end
def test_class_write_encrypted_cipher
key = @SEC.create_key 1024
key = @SEC.create_key 'rsa'
path = File.join @tempdir, 'test-private_encrypted__with_non_default_cipher_key.pem'