Forum: Ruby-core [ruby-trunk - Bug #6122][Open] OpenSSL::PKCS7 verify

Issue #6122 has been reported by Justin Peal.

----------------------------------------
Bug #6122: OpenSSL::PKCS7 verify
https://bugs.ruby-lang.org/issues/6122

Author: Justin Peal
Status: Open
Priority: High
Assignee:
Category:
Target version:
ruby -v: ruby 1.9.3p125 (2012-02-16) [i386-mingw32]


# not_after can not later than 2038-01-19 11:14:07
# verify can pass wrong certificate

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
# wrong.sign fa.key   # Don't sign indeed!

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered==plain ? recovered : "It's okay!"

Issue #6122 has been updated by Justin Peal.


# not_after can not later than 2038-01-19 11:14:07

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store, nil, 
OpenSSL::PKCS7::NOINTERN | OpenSSL::PKCS7::NOCHAIN)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
wrong.sign fa.key

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, right.cert, ca.cert)
puts recovered==plain ? "It's okay!" : recovered;
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered!=plain ? "It's okay!" : recovered;

----------------------------------------
Bug #6122: OpenSSL::PKCS7 verify
https://bugs.ruby-lang.org/issues/6122

Author: Justin Peal
Status: Open
Priority: High
Assignee:
Category:
Target version:
ruby -v: ruby 1.9.3p125 (2012-02-16) [i386-mingw32]


# not_after can not later than 2038-01-19 11:14:07
# verify can pass wrong certificate

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
# wrong.sign fa.key   # Don't sign indeed!

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered==plain ? recovered : "It's okay!"

Issue #6122 has been updated by Martin Bosslet.

Category set to ext
Assignee set to Martin Bosslet
Target version set to 2.0.0


----------------------------------------
Bug #6122: OpenSSL::PKCS7 verify
https://bugs.ruby-lang.org/issues/6122

Author: Justin Peal
Status: Open
Priority: High
Assignee: Martin Bosslet
Category: ext
Target version: 2.0.0
ruby -v: ruby 1.9.3p125 (2012-02-16) [i386-mingw32]


# not_after can not later than 2038-01-19 11:14:07
# verify can pass wrong certificate

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
# wrong.sign fa.key   # Don't sign indeed!

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered==plain ? recovered : "It's okay!"

Issue #6122 has been updated by MartinBosslet (Martin Bosslet).

Status changed from Assigned to Closed

Hi Justin,

The behavior you encountered is not an error. When you sign the PKCS7, 
the signing certificate will be included in the resulting SignedData 
structure. You can see that:

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    signed.certificates.each { |c| p c } # => the signing certificate is 
in there
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end

When the PKCS7 is verified later on, OpenSSL will at first look through 
the certificates you provided and then look in the SignedData itself if 
it can find the signing certificate there. It does, so it ignores your 
additional certificate. With the signing certificate included,

  signed.verify(nil, cert_store)

will also succeed, and this is expected. If you want it to behave 
differently, you may either use the flags as in your second example, or 
you might sign the data without including the signing certificates.

Regarding the time issue, you ran into the Y2K38 problem there. This 
shouldn't be a problem anymore with your Ruby version, and it works on 
my Linux machine, could be that it is a problem specific to Windows. 
I'll close this issue and open a separate one for the time problem as 
they are not related.
----------------------------------------
Bug #6122: OpenSSL::PKCS7 verify
https://bugs.ruby-lang.org/issues/6122#change-27148

Author: mghomn (Justin Peal)
Status: Closed
Priority: High
Assignee: MartinBosslet (Martin Bosslet)
Category: ext
Target version: 2.0.0
ruby -v: ruby 1.9.3p125 (2012-02-16) [i386-mingw32]


# not_after can not later than 2038-01-19 11:14:07
# verify can pass wrong certificate

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
# wrong.sign fa.key   # Don't sign indeed!

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered==plain ? recovered : "It's okay!"

Issue #6122 has been updated by MartinBosslet (Martin Bosslet).


Created https://bugs.ruby-lang.org/issues/6571 for the Time issue.
----------------------------------------
Bug #6122: OpenSSL::PKCS7 verify
https://bugs.ruby-lang.org/issues/6122#change-27149

Author: mghomn (Justin Peal)
Status: Closed
Priority: High
Assignee: MartinBosslet (Martin Bosslet)
Category: ext
Target version: 2.0.0
ruby -v: ruby 1.9.3p125 (2012-02-16) [i386-mingw32]


# not_after can not later than 2038-01-19 11:14:07
# verify can pass wrong certificate

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
# wrong.sign fa.key   # Don't sign indeed!

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered==plain ? recovered : "It's okay!"

Issue #6122 has been updated by mghomn (Justin Peal).


Thanks a lot!
----------------------------------------
Bug #6122: OpenSSL::PKCS7 verify
https://bugs.ruby-lang.org/issues/6122#change-34465

Author: mghomn (Justin Peal)
Status: Closed
Priority: High
Assignee: MartinBosslet (Martin Bosslet)
Category: ext
Target version: 2.0.0
ruby -v: ruby 1.9.3p125 (2012-02-16) [i386-mingw32]


# not_after can not later than 2038-01-19 11:14:07
# verify can pass wrong certificate

require 'OpenSSL'

class Rsa
    attr_reader :key, :cert
    @@sha = OpenSSL::Digest::SHA1.new
    @@aes = OpenSSL::Cipher.new("aes-128-ofb")

    def initialize serial, issuer=nil
      @key = OpenSSL::PKey::RSA.new(1024)
      @cert = OpenSSL::X509::Certificate.new
      @cert.version = 2   # RFC 5280 - v3
      @cert.serial = serial
      @cert.subject = OpenSSL::X509::Name.parse "CN=#{serial}"
      @cert.issuer = issuer==nil ? @cert.subject : issuer
      @cert.public_key = @key.public_key
      @cert.not_before = Time.now
      @cert.not_after = Time.mktime(2038, 1, 19, 11, 14, 7)   # second = 
8 ==> Fail!
      @cert.sign(@key, @@sha) if issuer==nil
    end

    def sign key
      @cert.sign(key, @@sha)
    end

  def sign_encrypt(plain, obj_cert)
    signed = OpenSSL::PKCS7::sign(@cert, @key, plain)
    encrypted = OpenSSL::PKCS7::encrypt([obj_cert], signed.to_s, @@aes)
  end

  def decrypt_verify(received, obj_cert, ca_cert)
    encrypted = OpenSSL::PKCS7.new(received)
    decrypted = encrypted.decrypt(@key, @cert)
    signed = OpenSSL::PKCS7.new(decrypted)
    cert_store = OpenSSL::X509::Store.new.add_cert(ca_cert)
    plain = signed.data if signed.verify([obj_cert], cert_store)
  end
end

ca = Rsa.new(1)
alice = Rsa.new(11, ca.cert.issuer)
alice.sign ca.key
right = Rsa.new(12, ca.cert.issuer)
right.sign ca.key

fa = Rsa.new(3)
wrong = Rsa.new(33, fa.cert.issuer)
# wrong.sign fa.key   # Don't sign indeed!

plain = "Something's wrong."
signed_encrypted = right.sign_encrypt(plain, alice.cert)
recovered = alice.decrypt_verify(signed_encrypted, wrong.cert, ca.cert) 
# wrong should be right
puts recovered==plain ? recovered : "It's okay!"