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Edit File : security.rb \| Size : 21.24 KB
# frozen_string_literal: true #-- # Copyright 2006 by Chad Fowler, Rich Kilmer, Jim Weirich and others. # All rights reserved. # See LICENSE.txt for permissions. #++ require 'rubygems/exceptions' require 'fileutils' begin require 'openssl' rescue LoadError => e raise unless (e.respond_to?(:path) && e.path == 'openssl') \|\| e.message =~ / -- openssl$/ end ## # = Signing gems # # The Gem::Security implements cryptographic signatures for gems. The section # below is a step-by-step guide to using signed gems and generating your own. # # == Walkthrough # # === Building your certificate # # In order to start signing your gems, you'll need to build a private key and # a self-signed certificate. Here's how: # # # build a private key and certificate for yourself: # $ gem cert --build you@example.com # # This could take anywhere from a few seconds to a minute or two, depending on # the speed of your computer (public key algorithms aren't exactly the # speediest crypto algorithms in the world). When it's finished, you'll see # the files "gem-private_key.pem" and "gem-public_cert.pem" in the current # directory. # # First things first: Move both files to ~/.gem if you don't already have a # key and certificate in that directory. Ensure the file permissions make the # key unreadable by others (by default the file is saved securely). # # Keep your private key hidden; if it's compromised, someone can sign packages # as you (note: PKI has ways of mitigating the risk of stolen keys; more on # that later). # # === Signing Gems # # In RubyGems 2 and newer there is no extra work to sign a gem. RubyGems will # automatically find your key and certificate in your home directory and use # them to sign newly packaged gems. # # If your certificate is not self-signed (signed by a third party) RubyGems # will attempt to load the certificate chain from the trusted certificates. # Use <code>gem cert --add signing_cert.pem</code> to add your signers as # trusted certificates. See below for further information on certificate # chains. # # If you build your gem it will automatically be signed. If you peek inside # your gem file, you'll see a couple of new files have been added: # # $ tar tf your-gem-1.0.gem # metadata.gz # metadata.gz.sum # metadata.gz.sig # metadata signature # data.tar.gz # data.tar.gz.sum # data.tar.gz.sig # data signature # # === Manually signing gems # # If you wish to store your key in a separate secure location you'll need to # set your gems up for signing by hand. To do this, set the # <code>signing_key</code> and <code>cert_chain</code> in the gemspec before # packaging your gem: # # s.signing_key = '/secure/path/to/gem-private_key.pem' # s.cert_chain = %w[/secure/path/to/gem-public_cert.pem] # # When you package your gem with these options set RubyGems will automatically # load your key and certificate from the secure paths. # # === Signed gems and security policies # # Now let's verify the signature. Go ahead and install the gem, but add the # following options: <code>-P HighSecurity</code>, like this: # # # install the gem with using the security policy "HighSecurity" # $ sudo gem install your.gem -P HighSecurity # # The <code>-P</code> option sets your security policy -- we'll talk about # that in just a minute. Eh, what's this? # # $ gem install -P HighSecurity your-gem-1.0.gem # ERROR: While executing gem ... (Gem::Security::Exception) # root cert /CN=you/DC=example is not trusted # # The culprit here is the security policy. RubyGems has several different # security policies. Let's take a short break and go over the security # policies. Here's a list of the available security policies, and a brief # description of each one: # # * NoSecurity - Well, no security at all. Signed packages are treated like # unsigned packages. # * LowSecurity - Pretty much no security. If a package is signed then # RubyGems will make sure the signature matches the signing # certificate, and that the signing certificate hasn't expired, but # that's it. A malicious user could easily circumvent this kind of # security. # * MediumSecurity - Better than LowSecurity and NoSecurity, but still # fallible. Package contents are verified against the signing # certificate, and the signing certificate is checked for validity, # and checked against the rest of the certificate chain (if you don't # know what a certificate chain is, stay tuned, we'll get to that). # The biggest improvement over LowSecurity is that MediumSecurity # won't install packages that are signed by untrusted sources. # Unfortunately, MediumSecurity still isn't totally secure -- a # malicious user can still unpack the gem, strip the signatures, and # distribute the gem unsigned. # * HighSecurity - Here's the bugger that got us into this mess. # The HighSecurity policy is identical to the MediumSecurity policy, # except that it does not allow unsigned gems. A malicious user # doesn't have a whole lot of options here; they can't modify the # package contents without invalidating the signature, and they can't # modify or remove signature or the signing certificate chain, or # RubyGems will simply refuse to install the package. Oh well, maybe # they'll have better luck causing problems for CPAN users instead :). # # The reason RubyGems refused to install your shiny new signed gem was because # it was from an untrusted source. Well, your code is infallible (naturally), # so you need to add yourself as a trusted source: # # # add trusted certificate # gem cert --add ~/.gem/gem-public_cert.pem # # You've now added your public certificate as a trusted source. Now you can # install packages signed by your private key without any hassle. Let's try # the install command above again: # # # install the gem with using the HighSecurity policy (and this time # # without any shenanigans) # $ gem install -P HighSecurity your-gem-1.0.gem # Successfully installed your-gem-1.0 # 1 gem installed # # This time RubyGems will accept your signed package and begin installing. # # While you're waiting for RubyGems to work it's magic, have a look at some of # the other security commands by running <code>gem help cert</code>: # # Options: # -a, --add CERT Add a trusted certificate. # -l, --list [FILTER] List trusted certificates where the # subject contains FILTER # -r, --remove FILTER Remove trusted certificates where the # subject contains FILTER # -b, --build EMAIL_ADDR Build private key and self-signed # certificate for EMAIL_ADDR # -C, --certificate CERT Signing certificate for --sign # -K, --private-key KEY Key for --sign or --build # -s, --sign CERT Signs CERT with the key from -K # and the certificate from -C # # We've already covered the <code>--build</code> option, and the # <code>--add</code>, <code>--list</code>, and <code>--remove</code> commands # seem fairly straightforward; they allow you to add, list, and remove the # certificates in your trusted certificate list. But what's with this # <code>--sign</code> option? # # === Certificate chains # # To answer that question, let's take a look at "certificate chains", a # concept I mentioned earlier. There are a couple of problems with # self-signed certificates: first of all, self-signed certificates don't offer # a whole lot of security. Sure, the certificate says Yukihiro Matsumoto, but # how do I know it was actually generated and signed by matz himself unless he # gave me the certificate in person? # # The second problem is scalability. Sure, if there are 50 gem authors, then # I have 50 trusted certificates, no problem. What if there are 500 gem # authors? 1000? Having to constantly add new trusted certificates is a # pain, and it actually makes the trust system less secure by encouraging # RubyGems users to blindly trust new certificates. # # Here's where certificate chains come in. A certificate chain establishes an # arbitrarily long chain of trust between an issuing certificate and a child # certificate. So instead of trusting certificates on a per-developer basis, # we use the PKI concept of certificate chains to build a logical hierarchy of # trust. Here's a hypothetical example of a trust hierarchy based (roughly) # on geography: # # -------------------------- # \| rubygems@rubygems.org \| # -------------------------- # \| # ----------------------------------- # \| \| # ---------------------------- ----------------------------- # \| seattlerb@seattlerb.org \| \| dcrubyists@richkilmer.com \| # ---------------------------- ----------------------------- # \| \| \| \| # --------------- ---------------- ----------- -------------- # \| drbrain \| \| zenspider \| \| pabs@dc \| \| tomcope@dc \| # --------------- ---------------- ----------- -------------- # # # Now, rather than having 4 trusted certificates (one for drbrain, zenspider, # pabs@dc, and tomecope@dc), a user could actually get by with one # certificate, the "rubygems@rubygems.org" certificate. # # Here's how it works: # # I install "rdoc-3.12.gem", a package signed by "drbrain". I've never heard # of "drbrain", but his certificate has a valid signature from the # "seattle.rb@seattlerb.org" certificate, which in turn has a valid signature # from the "rubygems@rubygems.org" certificate. Voila! At this point, it's # much more reasonable for me to trust a package signed by "drbrain", because # I can establish a chain to "rubygems@rubygems.org", which I do trust. # # === Signing certificates # # The <code>--sign</code> option allows all this to happen. A developer # creates their build certificate with the <code>--build</code> option, then # has their certificate signed by taking it with them to their next regional # Ruby meetup (in our hypothetical example), and it's signed there by the # person holding the regional RubyGems signing certificate, which is signed at # the next RubyConf by the holder of the top-level RubyGems certificate. At # each point the issuer runs the same command: # # # sign a certificate with the specified key and certificate # # (note that this modifies client_cert.pem!) # $ gem cert -K /mnt/floppy/issuer-priv_key.pem -C issuer-pub_cert.pem # --sign client_cert.pem # # Then the holder of issued certificate (in this case, your buddy "drbrain"), # can start using this signed certificate to sign RubyGems. By the way, in # order to let everyone else know about his new fancy signed certificate, # "drbrain" would save his newly signed certificate as # <code>~/.gem/gem-public_cert.pem</code> # # Obviously this RubyGems trust infrastructure doesn't exist yet. Also, in # the "real world", issuers actually generate the child certificate from a # certificate request, rather than sign an existing certificate. And our # hypothetical infrastructure is missing a certificate revocation system. # These are that can be fixed in the future... # # At this point you should know how to do all of these new and interesting # things: # # * build a gem signing key and certificate # * adjust your security policy # * modify your trusted certificate list # * sign a certificate # # == Manually verifying signatures # # In case you don't trust RubyGems you can verify gem signatures manually: # # 1. Fetch and unpack the gem # # gem fetch some_signed_gem # tar -xf some_signed_gem-1.0.gem # # 2. Grab the public key from the gemspec # # gem spec some_signed_gem-1.0.gem cert_chain \| \ # ruby -ryaml -e 'puts YAML.load_documents($stdin)' > public_key.crt # # 3. Generate a SHA1 hash of the data.tar.gz # # openssl dgst -sha1 < data.tar.gz > my.hash # # 4. Verify the signature # # openssl rsautl -verify -inkey public_key.crt -certin \ # -in data.tar.gz.sig > verified.hash # # 5. Compare your hash to the verified hash # # diff -s verified.hash my.hash # # 6. Repeat 5 and 6 with metadata.gz # # == OpenSSL Reference # # The .pem files generated by --build and --sign are PEM files. Here's a # couple of useful OpenSSL commands for manipulating them: # # # convert a PEM format X509 certificate into DER format: # # (note: Windows .cer files are X509 certificates in DER format) # $ openssl x509 -in input.pem -outform der -out output.der # # # print out the certificate in a human-readable format: # $ openssl x509 -in input.pem -noout -text # # And you can do the same thing with the private key file as well: # # # convert a PEM format RSA key into DER format: # $ openssl rsa -in input_key.pem -outform der -out output_key.der # # # print out the key in a human readable format: # $ openssl rsa -in input_key.pem -noout -text # # == Bugs/TODO # # * There's no way to define a system-wide trust list. # * custom security policies (from a YAML file, etc) # * Simple method to generate a signed certificate request # * Support for OCSP, SCVP, CRLs, or some other form of cert status check # (list is in order of preference) # * Support for encrypted private keys # * Some sort of semi-formal trust hierarchy (see long-winded explanation # above) # * Path discovery (for gem certificate chains that don't have a self-signed # root) -- by the way, since we don't have this, THE ROOT OF THE CERTIFICATE # CHAIN MUST BE SELF SIGNED if Policy#verify_root is true (and it is for the # MediumSecurity and HighSecurity policies) # * Better explanation of X509 naming (ie, we don't have to use email # addresses) # * Honor AIA field (see note about OCSP above) # * 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 # # Paul Duncan <pabs@pablotron.org> # http://pablotron.org/ module Gem::Security ## # Gem::Security default exception type class Exception < Gem::Exception; end ## # Digest algorithm used to sign gems DIGEST_ALGORITHM = if defined?(OpenSSL::Digest::SHA256) OpenSSL::Digest::SHA256 elsif defined?(OpenSSL::Digest::SHA1) OpenSSL::Digest::SHA1 else require 'digest' Digest::SHA512 end ## # Used internally to select the signing digest from all computed digests DIGEST_NAME = # :nodoc: if DIGEST_ALGORITHM.method_defined? :name DIGEST_ALGORITHM.new.name else DIGEST_ALGORITHM.name[/::([^:]+)\z/, 1] end ## # Algorithm for creating the key pair used to sign gems KEY_ALGORITHM = if defined?(OpenSSL::PKey::RSA) OpenSSL::PKey::RSA end ## # Length of keys created by KEY_ALGORITHM KEY_LENGTH = 3072 ## # Cipher used to encrypt the key pair used to sign gems. # Must be in the list returned by OpenSSL::Cipher.ciphers KEY_CIPHER = OpenSSL::Cipher.new('AES-256-CBC') if defined?(OpenSSL::Cipher) ## # One day in seconds ONE_DAY = 86400 ## # One year in seconds ONE_YEAR = ONE_DAY * 365 ## # The default set of extensions are: # # * The certificate is not a certificate authority # * The key for the certificate may be used for key and data encipherment # and digital signatures # * The certificate contains a subject key identifier EXTENSIONS = { 'basicConstraints' => 'CA:FALSE', 'keyUsage' => 'keyEncipherment,dataEncipherment,digitalSignature', 'subjectKeyIdentifier' => 'hash', }.freeze def self.alt_name_or_x509_entry(certificate, x509_entry) alt_name = certificate.extensions.find do \|extension\| extension.oid == "#{x509_entry}AltName" end return alt_name.value if alt_name certificate.send x509_entry end ## # Creates an unsigned certificate for +subject+ and +key+. The lifetime of # the key is from the current time to +age+ which defaults to one year. # # The +extensions+ restrict the key to the indicated uses. def self.create_cert(subject, key, age = ONE_YEAR, extensions = EXTENSIONS, serial = 1) cert = OpenSSL::X509::Certificate.new cert.public_key = key.public_key cert.version = 2 cert.serial = serial cert.not_before = Time.now cert.not_after = Time.now + age cert.subject = subject ef = OpenSSL::X509::ExtensionFactory.new nil, cert cert.extensions = extensions.map do \|ext_name, value\| ef.create_extension ext_name, value end cert 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 # +key+. def self.create_cert_email(email, key, age = ONE_YEAR, extensions = EXTENSIONS) subject = email_to_name email extensions = extensions.merge "subjectAltName" => "email:#{email}" create_cert_self_signed subject, key, age, extensions end ## # Creates a self-signed certificate with an issuer and subject of +subject+ # and the given +extensions+ for the +key+. def self.create_cert_self_signed(subject, key, age = ONE_YEAR, extensions = EXTENSIONS, serial = 1) certificate = create_cert subject, key, age, extensions sign certificate, key, certificate, age, extensions, serial end ## # Creates a new key pair of the specified +length+ and +algorithm+. The # default is a 3072 bit RSA key. def self.create_key(length = KEY_LENGTH, algorithm = KEY_ALGORITHM) algorithm.new length end ## # Turns +email_address+ into an OpenSSL::X509::Name def self.email_to_name(email_address) email_address = email_address.gsub(/[^\w@.-]+/i, '_') cn, dcs = email_address.split '@' dcs = dcs.split '.' name = "CN=#{cn}/#{dcs.map { \|dc\| "DC=#{dc}" }.join '/'}" OpenSSL::X509::Name.parse name end ## # Signs +expired_certificate+ with +private_key+ if the keys match and the # expired certificate was self-signed. #-- # TODO increment serial def self.re_sign(expired_certificate, private_key, age = ONE_YEAR, extensions = EXTENSIONS) 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 unless expired_certificate.subject.to_s == expired_certificate.issuer.to_s subject = alt_name_or_x509_entry expired_certificate, :subject issuer = alt_name_or_x509_entry expired_certificate, :issuer raise Gem::Security::Exception, "#{subject} is not self-signed, contact #{issuer} " + "to obtain a valid certificate" end serial = expired_certificate.serial + 1 create_cert_self_signed(expired_certificate.subject, private_key, age, extensions, serial) end ## # Resets the trust directory for verifying gems. def self.reset @trust_dir = nil end ## # Sign the public key from +certificate+ with the +signing_key+ and # +signing_cert+, using the Gem::Security::DIGEST_ALGORITHM. Uses the # default certificate validity range and extensions. # # Returns the newly signed certificate. def self.sign(certificate, signing_key, signing_cert, age = ONE_YEAR, extensions = EXTENSIONS, serial = 1) signee_subject = certificate.subject signee_key = certificate.public_key alt_name = certificate.extensions.find do \|extension\| extension.oid == 'subjectAltName' end extensions = extensions.merge 'subjectAltName' => alt_name.value if alt_name issuer_alt_name = signing_cert.extensions.find do \|extension\| extension.oid == 'subjectAltName' end extensions = extensions.merge 'issuerAltName' => issuer_alt_name.value if issuer_alt_name signed = create_cert signee_subject, signee_key, age, extensions, serial signed.issuer = signing_cert.subject signed.sign signing_key, Gem::Security::DIGEST_ALGORITHM.new end ## # Returns a Gem::Security::TrustDir which wraps the directory where trusted # certificates live. def self.trust_dir return @trust_dir if @trust_dir dir = File.join Gem.user_home, '.gem', 'trust' @trust_dir \|\|= Gem::Security::TrustDir.new dir end ## # Enumerates the trusted certificates via Gem::Security::TrustDir. def self.trusted_certificates(&block) trust_dir.each_certificate(&block) end ## # Writes +pemmable+, which must respond to +to_pem+ to +path+ with the given # +permissions+. If passed +cipher+ and +passphrase+ those arguments will be # passed to +to_pem+. def self.write(pemmable, path, permissions = 0600, passphrase = nil, cipher = KEY_CIPHER) path = File.expand_path path File.open path, 'wb', permissions do \|io\| if passphrase and cipher io.write pemmable.to_pem cipher, passphrase else io.write pemmable.to_pem end end path end reset end if defined?(OpenSSL::SSL) require 'rubygems/security/policy' require 'rubygems/security/policies' require 'rubygems/security/trust_dir' end require 'rubygems/security/signer' Back

Edit File : security.rb | Size : 21.24 KB

# frozen_string_literal: true
#--
# Copyright 2006 by Chad Fowler, Rich Kilmer, Jim Weirich and others.
# All rights reserved.
# See LICENSE.txt for permissions.
#++

require 'rubygems/exceptions'
require 'fileutils'

begin
  require 'openssl'
rescue LoadError => e
  raise unless (e.respond_to?(:path) && e.path == 'openssl') ||
               e.message =~ / -- openssl$/
end

##
# = Signing gems
#
# The Gem::Security implements cryptographic signatures for gems.  The section
# below is a step-by-step guide to using signed gems and generating your own.
#
# == Walkthrough
#
# === Building your certificate
#
# In order to start signing your gems, you'll need to build a private key and
# a self-signed certificate.  Here's how:
#
#   # build a private key and certificate for yourself:
#   $ gem cert --build you@example.com
#
# This could take anywhere from a few seconds to a minute or two, depending on
# the speed of your computer (public key algorithms aren't exactly the
# speediest crypto algorithms in the world).  When it's finished, you'll see
# the files "gem-private_key.pem" and "gem-public_cert.pem" in the current
# directory.
#
# First things first: Move both files to ~/.gem if you don't already have a
# key and certificate in that directory.  Ensure the file permissions make the
# key unreadable by others (by default the file is saved securely).
#
# Keep your private key hidden; if it's compromised, someone can sign packages
# as you (note: PKI has ways of mitigating the risk of stolen keys; more on
# that later).
#
# === Signing Gems
#
# In RubyGems 2 and newer there is no extra work to sign a gem.  RubyGems will
# automatically find your key and certificate in your home directory and use
# them to sign newly packaged gems.
#
# If your certificate is not self-signed (signed by a third party) RubyGems
# will attempt to load the certificate chain from the trusted certificates.
# Use <code>gem cert --add signing_cert.pem</code> to add your signers as
# trusted certificates.  See below for further information on certificate
# chains.
#
# If you build your gem it will automatically be signed.  If you peek inside
# your gem file, you'll see a couple of new files have been added:
#
#   $ tar tf your-gem-1.0.gem
#   metadata.gz
#   metadata.gz.sum
#   metadata.gz.sig # metadata signature
#   data.tar.gz
#   data.tar.gz.sum
#   data.tar.gz.sig # data signature
#
# === Manually signing gems
#
# If you wish to store your key in a separate secure location you'll need to
# set your gems up for signing by hand.  To do this, set the
# <code>signing_key</code> and <code>cert_chain</code> in the gemspec before
# packaging your gem:
#
#   s.signing_key = '/secure/path/to/gem-private_key.pem'
#   s.cert_chain = %w[/secure/path/to/gem-public_cert.pem]
#
# When you package your gem with these options set RubyGems will automatically
# load your key and certificate from the secure paths.
#
# === Signed gems and security policies
#
# Now let's verify the signature.  Go ahead and install the gem, but add the
# following options: <code>-P HighSecurity</code>, like this:
#
#   # install the gem with using the security policy "HighSecurity"
#   $ sudo gem install your.gem -P HighSecurity
#
# The <code>-P</code> option sets your security policy -- we'll talk about
# that in just a minute.  Eh, what's this?
#
#   $ gem install -P HighSecurity your-gem-1.0.gem
#   ERROR:  While executing gem ... (Gem::Security::Exception)
#       root cert /CN=you/DC=example is not trusted
#
# The culprit here is the security policy.  RubyGems has several different
# security policies.  Let's take a short break and go over the security
# policies.  Here's a list of the available security policies, and a brief
# description of each one:
#
# * NoSecurity - Well, no security at all.  Signed packages are treated like
#   unsigned packages.
# * LowSecurity - Pretty much no security.  If a package is signed then
#   RubyGems will make sure the signature matches the signing
#   certificate, and that the signing certificate hasn't expired, but
#   that's it.  A malicious user could easily circumvent this kind of
#   security.
# * MediumSecurity - Better than LowSecurity and NoSecurity, but still
#   fallible.  Package contents are verified against the signing
#   certificate, and the signing certificate is checked for validity,
#   and checked against the rest of the certificate chain (if you don't
#   know what a certificate chain is, stay tuned, we'll get to that).
#   The biggest improvement over LowSecurity is that MediumSecurity
#   won't install packages that are signed by untrusted sources.
#   Unfortunately, MediumSecurity still isn't totally secure -- a
#   malicious user can still unpack the gem, strip the signatures, and
#   distribute the gem unsigned.
# * HighSecurity - Here's the bugger that got us into this mess.
#   The HighSecurity policy is identical to the MediumSecurity policy,
#   except that it does not allow unsigned gems.  A malicious user
#   doesn't have a whole lot of options here; they can't modify the
#   package contents without invalidating the signature, and they can't
#   modify or remove signature or the signing certificate chain, or
#   RubyGems will simply refuse to install the package.  Oh well, maybe
#   they'll have better luck causing problems for CPAN users instead :).
#
# The reason RubyGems refused to install your shiny new signed gem was because
# it was from an untrusted source.  Well, your code is infallible (naturally),
# so you need to add yourself as a trusted source:
#
#   # add trusted certificate
#   gem cert --add ~/.gem/gem-public_cert.pem
#
# You've now added your public certificate as a trusted source.  Now you can
# install packages signed by your private key without any hassle.  Let's try
# the install command above again:
#
#   # install the gem with using the HighSecurity policy (and this time
#   # without any shenanigans)
#   $ gem install -P HighSecurity your-gem-1.0.gem
#   Successfully installed your-gem-1.0
#   1 gem installed
#
# This time RubyGems will accept your signed package and begin installing.
#
# While you're waiting for RubyGems to work it's magic, have a look at some of
# the other security commands by running <code>gem help cert</code>:
#
#   Options:
#     -a, --add CERT                   Add a trusted certificate.
#     -l, --list [FILTER]              List trusted certificates where the
#                                      subject contains FILTER
#     -r, --remove FILTER              Remove trusted certificates where the
#                                      subject contains FILTER
#     -b, --build EMAIL_ADDR           Build private key and self-signed
#                                      certificate for EMAIL_ADDR
#     -C, --certificate CERT           Signing certificate for --sign
#     -K, --private-key KEY            Key for --sign or --build
#     -s, --sign CERT                  Signs CERT with the key from -K
#                                      and the certificate from -C
#
# We've already covered the <code>--build</code> option, and the
# <code>--add</code>, <code>--list</code>, and <code>--remove</code> commands
# seem fairly straightforward; they allow you to add, list, and remove the
# certificates in your trusted certificate list.  But what's with this
# <code>--sign</code> option?
#
# === Certificate chains
#
# To answer that question, let's take a look at "certificate chains", a
# concept I mentioned earlier.  There are a couple of problems with
# self-signed certificates: first of all, self-signed certificates don't offer
# a whole lot of security.  Sure, the certificate says Yukihiro Matsumoto, but
# how do I know it was actually generated and signed by matz himself unless he
# gave me the certificate in person?
#
# The second problem is scalability.  Sure, if there are 50 gem authors, then
# I have 50 trusted certificates, no problem.  What if there are 500 gem
# authors?  1000?  Having to constantly add new trusted certificates is a
# pain, and it actually makes the trust system less secure by encouraging
# RubyGems users to blindly trust new certificates.
#
# Here's where certificate chains come in.  A certificate chain establishes an
# arbitrarily long chain of trust between an issuing certificate and a child
# certificate.  So instead of trusting certificates on a per-developer basis,
# we use the PKI concept of certificate chains to build a logical hierarchy of
# trust.  Here's a hypothetical example of a trust hierarchy based (roughly)
# on geography:
#
#                         --------------------------
#                         | rubygems@rubygems.org |
#                         --------------------------
#                                     |
#                   -----------------------------------
#                   |                                 |
#       ----------------------------    -----------------------------
#       |  seattlerb@seattlerb.org |    | dcrubyists@richkilmer.com |
#       ----------------------------    -----------------------------
#            |                |                 |             |
#     ---------------   ----------------   -----------   --------------
#     |   drbrain   |   |   zenspider  |   | pabs@dc |   | tomcope@dc |
#     ---------------   ----------------   -----------   --------------
#
#
# Now, rather than having 4 trusted certificates (one for drbrain, zenspider,
# pabs@dc, and tomecope@dc), a user could actually get by with one
# certificate, the "rubygems@rubygems.org" certificate.
#
# Here's how it works:
#
# I install "rdoc-3.12.gem", a package signed by "drbrain".  I've never heard
# of "drbrain", but his certificate has a valid signature from the
# "seattle.rb@seattlerb.org" certificate, which in turn has a valid signature
# from the "rubygems@rubygems.org" certificate.  Voila!  At this point, it's
# much more reasonable for me to trust a package signed by "drbrain", because
# I can establish a chain to "rubygems@rubygems.org", which I do trust.
#
# === Signing certificates
#
# The <code>--sign</code> option allows all this to happen.  A developer
# creates their build certificate with the <code>--build</code> option, then
# has their certificate signed by taking it with them to their next regional
# Ruby meetup (in our hypothetical example), and it's signed there by the
# person holding the regional RubyGems signing certificate, which is signed at
# the next RubyConf by the holder of the top-level RubyGems certificate.  At
# each point the issuer runs the same command:
#
#   # sign a certificate with the specified key and certificate
#   # (note that this modifies client_cert.pem!)
#   $ gem cert -K /mnt/floppy/issuer-priv_key.pem -C issuer-pub_cert.pem
#      --sign client_cert.pem
#
# Then the holder of issued certificate (in this case, your buddy "drbrain"),
# can start using this signed certificate to sign RubyGems.  By the way, in
# order to let everyone else know about his new fancy signed certificate,
# "drbrain" would save his newly signed certificate as
# <code>~/.gem/gem-public_cert.pem</code>
#
# Obviously this RubyGems trust infrastructure doesn't exist yet.  Also, in
# the "real world", issuers actually generate the child certificate from a
# certificate request, rather than sign an existing certificate.  And our
# hypothetical infrastructure is missing a certificate revocation system.
# These are that can be fixed in the future...
#
# At this point you should know how to do all of these new and interesting
# things:
#
# * build a gem signing key and certificate
# * adjust your security policy
# * modify your trusted certificate list
# * sign a certificate
#
# == Manually verifying signatures
#
# In case you don't trust RubyGems you can verify gem signatures manually:
#
# 1. Fetch and unpack the gem
#
#      gem fetch some_signed_gem
#      tar -xf some_signed_gem-1.0.gem
#
# 2. Grab the public key from the gemspec
#
#      gem spec some_signed_gem-1.0.gem cert_chain | \
#        ruby -ryaml -e 'puts YAML.load_documents($stdin)' > public_key.crt
#
# 3. Generate a SHA1 hash of the data.tar.gz
#
#      openssl dgst -sha1 < data.tar.gz > my.hash
#
# 4. Verify the signature
#
#      openssl rsautl -verify -inkey public_key.crt -certin \
#        -in data.tar.gz.sig > verified.hash
#
# 5. Compare your hash to the verified hash
#
#      diff -s verified.hash my.hash
#
# 6. Repeat 5 and 6 with metadata.gz
#
# == OpenSSL Reference
#
# The .pem files generated by --build and --sign are PEM files.  Here's a
# couple of useful OpenSSL commands for manipulating them:
#
#   # convert a PEM format X509 certificate into DER format:
#   # (note: Windows .cer files are X509 certificates in DER format)
#   $ openssl x509 -in input.pem -outform der -out output.der
#
#   # print out the certificate in a human-readable format:
#   $ openssl x509 -in input.pem -noout -text
#
# And you can do the same thing with the private key file as well:
#
#   # convert a PEM format RSA key into DER format:
#   $ openssl rsa -in input_key.pem -outform der -out output_key.der
#
#   # print out the key in a human readable format:
#   $ openssl rsa -in input_key.pem -noout -text
#
# == Bugs/TODO
#
# * There's no way to define a system-wide trust list.
# * custom security policies (from a YAML file, etc)
# * Simple method to generate a signed certificate request
# * Support for OCSP, SCVP, CRLs, or some other form of cert status check
#   (list is in order of preference)
# * Support for encrypted private keys
# * Some sort of semi-formal trust hierarchy (see long-winded explanation
#   above)
# * Path discovery (for gem certificate chains that don't have a self-signed
#   root) -- by the way, since we don't have this, THE ROOT OF THE CERTIFICATE
#   CHAIN MUST BE SELF SIGNED if Policy#verify_root is true (and it is for the
#   MediumSecurity and HighSecurity policies)
# * Better explanation of X509 naming (ie, we don't have to use email
#   addresses)
# * Honor AIA field (see note about OCSP above)
# * 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
#
# Paul Duncan <pabs@pablotron.org>
# http://pablotron.org/

module Gem::Security

##
  # Gem::Security default exception type

class Exception < Gem::Exception; end

##
  # Digest algorithm used to sign gems

DIGEST_ALGORITHM =
    if defined?(OpenSSL::Digest::SHA256)
      OpenSSL::Digest::SHA256
    elsif defined?(OpenSSL::Digest::SHA1)
      OpenSSL::Digest::SHA1
    else
      require 'digest'
      Digest::SHA512
    end

##
  # Used internally to select the signing digest from all computed digests

DIGEST_NAME = # :nodoc:
    if DIGEST_ALGORITHM.method_defined? :name
      DIGEST_ALGORITHM.new.name
    else
      DIGEST_ALGORITHM.name[/::([^:]+)\z/, 1]
    end

##
  # Algorithm for creating the key pair used to sign gems

KEY_ALGORITHM =
    if defined?(OpenSSL::PKey::RSA)
      OpenSSL::PKey::RSA
    end

##
  # Length of keys created by KEY_ALGORITHM

KEY_LENGTH = 3072

##
  # Cipher used to encrypt the key pair used to sign gems.
  # Must be in the list returned by OpenSSL::Cipher.ciphers

KEY_CIPHER = OpenSSL::Cipher.new('AES-256-CBC') if defined?(OpenSSL::Cipher)

##
  # One day in seconds

ONE_DAY = 86400

##
  # One year in seconds

ONE_YEAR = ONE_DAY * 365

##
  # The default set of extensions are:
  #
  # * The certificate is not a certificate authority
  # * The key for the certificate may be used for key and data encipherment
  #   and digital signatures
  # * The certificate contains a subject key identifier

EXTENSIONS = {
    'basicConstraints'     => 'CA:FALSE',
    'keyUsage'             =>
      'keyEncipherment,dataEncipherment,digitalSignature',
    'subjectKeyIdentifier' => 'hash',
  }.freeze

def self.alt_name_or_x509_entry(certificate, x509_entry)
    alt_name = certificate.extensions.find do |extension|
      extension.oid == "#{x509_entry}AltName"
    end

return alt_name.value if alt_name

certificate.send x509_entry
  end

##
  # Creates an unsigned certificate for +subject+ and +key+.  The lifetime of
  # the key is from the current time to +age+ which defaults to one year.
  #
  # The +extensions+ restrict the key to the indicated uses.

def self.create_cert(subject, key, age = ONE_YEAR, extensions = EXTENSIONS,
                       serial = 1)
    cert = OpenSSL::X509::Certificate.new

cert.public_key = key.public_key
    cert.version    = 2
    cert.serial     = serial

cert.not_before = Time.now
    cert.not_after  = Time.now + age

cert.subject    = subject

ef = OpenSSL::X509::ExtensionFactory.new nil, cert

cert.extensions = extensions.map do |ext_name, value|
      ef.create_extension ext_name, value
    end

cert
  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
  # +key+.

def self.create_cert_email(email, key, age = ONE_YEAR, extensions = EXTENSIONS)
    subject = email_to_name email

extensions = extensions.merge "subjectAltName" => "email:#{email}"

create_cert_self_signed subject, key, age, extensions
  end

##
  # Creates a self-signed certificate with an issuer and subject of +subject+
  # and the given +extensions+ for the +key+.

def self.create_cert_self_signed(subject, key, age = ONE_YEAR,
                                   extensions = EXTENSIONS, serial = 1)
    certificate = create_cert subject, key, age, extensions

sign certificate, key, certificate, age, extensions, serial
  end

##
  # Creates a new key pair of the specified +length+ and +algorithm+.  The
  # default is a 3072 bit RSA key.

def self.create_key(length = KEY_LENGTH, algorithm = KEY_ALGORITHM)
    algorithm.new length
  end

##
  # Turns +email_address+ into an OpenSSL::X509::Name

def self.email_to_name(email_address)
    email_address = email_address.gsub(/[^\w@.-]+/i, '_')

cn, dcs = email_address.split '@'

dcs = dcs.split '.'

name = "CN=#{cn}/#{dcs.map { |dc| "DC=#{dc}" }.join '/'}"

OpenSSL::X509::Name.parse name
  end

##
  # Signs +expired_certificate+ with +private_key+ if the keys match and the
  # expired certificate was self-signed.
  #--
  # TODO increment serial

def self.re_sign(expired_certificate, private_key, age = ONE_YEAR,
                   extensions = EXTENSIONS)
    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

unless expired_certificate.subject.to_s ==
           expired_certificate.issuer.to_s
      subject = alt_name_or_x509_entry expired_certificate, :subject
      issuer  = alt_name_or_x509_entry expired_certificate, :issuer

raise Gem::Security::Exception,
            "#{subject} is not self-signed, contact #{issuer} " +
            "to obtain a valid certificate"
    end

serial = expired_certificate.serial + 1

create_cert_self_signed(expired_certificate.subject, private_key, age,
                            extensions, serial)
  end

##
  # Resets the trust directory for verifying gems.

def self.reset
    @trust_dir = nil
  end

##
  # Sign the public key from +certificate+ with the +signing_key+ and
  # +signing_cert+, using the Gem::Security::DIGEST_ALGORITHM.  Uses the
  # default certificate validity range and extensions.
  #
  # Returns the newly signed certificate.

def self.sign(certificate, signing_key, signing_cert,
                age = ONE_YEAR, extensions = EXTENSIONS, serial = 1)
    signee_subject = certificate.subject
    signee_key     = certificate.public_key

alt_name = certificate.extensions.find do |extension|
      extension.oid == 'subjectAltName'
    end

extensions = extensions.merge 'subjectAltName' => alt_name.value if
      alt_name

issuer_alt_name = signing_cert.extensions.find do |extension|
      extension.oid == 'subjectAltName'
    end

extensions = extensions.merge 'issuerAltName' => issuer_alt_name.value if
      issuer_alt_name

signed = create_cert signee_subject, signee_key, age, extensions, serial
    signed.issuer = signing_cert.subject

signed.sign signing_key, Gem::Security::DIGEST_ALGORITHM.new
  end

##
  # Returns a Gem::Security::TrustDir which wraps the directory where trusted
  # certificates live.

def self.trust_dir
    return @trust_dir if @trust_dir

dir = File.join Gem.user_home, '.gem', 'trust'

@trust_dir ||= Gem::Security::TrustDir.new dir
  end

##
  # Enumerates the trusted certificates via Gem::Security::TrustDir.

def self.trusted_certificates(&block)
    trust_dir.each_certificate(&block)
  end

##
  # Writes +pemmable+, which must respond to +to_pem+ to +path+ with the given
  # +permissions+. If passed +cipher+ and +passphrase+ those arguments will be
  # passed to +to_pem+.

def self.write(pemmable, path, permissions = 0600, passphrase = nil, cipher = KEY_CIPHER)
    path = File.expand_path path

File.open path, 'wb', permissions do |io|
      if passphrase and cipher
        io.write pemmable.to_pem cipher, passphrase
      else
        io.write pemmable.to_pem
      end
    end

path
  end

reset

end

if defined?(OpenSSL::SSL)
  require 'rubygems/security/policy'
  require 'rubygems/security/policies'
  require 'rubygems/security/trust_dir'
end

require 'rubygems/security/signer'

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