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ruby/ext/openssl/History.md

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Version 3.2.0

Compatibility

  • Ruby >= 2.7
    • Support for Ruby 2.6 has been removed. Note that Ruby 2.6 reached the end-of-life in 2022-04. [GitHub #639]
  • OpenSSL >= 1.0.2 or LibreSSL >= 3.1

Notable changes

  • Add a stub gemspec for JRuby, which depends on the jruby-openssl gem. [GitHub #598]
  • Add support for the FIPS module in OpenSSL 3.0/3.1. [GitHub #608]
  • Rework OpenSSL::PKey routines for loading DER or PEM encoded keys for better compatibility with OpenSSL 3.0/3.1 with the FIPS module. [GitHub #615] [GitHub #669]
  • Add OpenSSL::Provider module for loading and unloading OpenSSL 3 providers. [GitHub #635]
  • Add OpenSSL::PKey.new_raw_private_key, .new_raw_public_key, OpenSSL::PKey::PKey#raw_private_key, and #raw_public_key for public key algorithms that use "raw private/public key", such as X25519 and Ed25519. [GitHub #646]
  • Improve OpenSSL error messages to include additional information when it is available in OpenSSL's error queue. [GitHub #648]
  • Change OpenSSL::SSL::SSLContext#ca_file= and #ca_path= to raise OpenSSL::SSL::SSLError instead of printing a warning message. [GitHub #659]
  • Allow OpenSSL::X509::ExtensionFactory#create_extension to take OIDs in the dotted-decimal notation. [GitHub #141]

Version 3.1.0

Ruby/OpenSSL 3.1 will be maintained for the lifetime of Ruby 3.2.

Merged bug fixes in 2.2.3 and 3.0.2. Among the new features and changes are:

Notable changes

  • Add OpenSSL::SSL::SSLContext#ciphersuites= to allow setting TLS 1.3 cipher suites. [GitHub #493]
  • Add OpenSSL::SSL::SSLSocket#export_keying_material for exporting keying material of the session, as defined in RFC 5705. [GitHub #530]
  • Add OpenSSL::SSL::SSLContext#keylog_cb= for setting the TLS key logging callback, which is useful for supporting NSS's SSLKEYLOGFILE debugging output. [GitHub #536]
  • Remove the default digest algorithm from OpenSSL::OCSP::BasicResponse#sign and OpenSSL::OCSP::Request#sign. Omitting the 5th parameter of these methods used to be equivalent of specifying SHA-1. This default value is now removed and we will let the underlying OpenSSL library decide instead. [GitHub #507]
  • Add OpenSSL::BN#mod_sqrt. [GitHub #553]
  • Allow calling OpenSSL::Cipher#update with an empty string. This was prohibited to workaround an ancient bug in OpenSSL. [GitHub #568]
  • Fix build on platforms without socket support, such as WASI. OpenSSL::SSL will not be defined if OpenSSL is compiled with OPENSSL_NO_SOCK. [GitHub #558]
  • Improve support for recent LibreSSL versions. This includes HKDF support in LibreSSL 3.6 and Ed25519 support in LibreSSL 3.7.

Version 3.0.2

Merged changes in 2.2.3. Additionally, the following issues are fixed by this release.

Bug fixes

Version 3.0.1

Merged changes in 2.1.4 and 2.2.2. Additionally, the following issues are fixed by this release.

Bug fixes

  • Add missing type check in OpenSSL::PKey::PKey#sign's optional parameters. [GitHub #531]
  • Work around OpenSSL 3.0's HMAC issues with a zero-length key. [GitHub #538]
  • Fix a regression in OpenSSL::PKey::DSA.generate's default of 'q' size. [GitHub #483] [GitHub #539]
  • Restore OpenSSL::PKey.read's ability to decode "openssl ecparam -genkey" output when linked against OpenSSL 3.0. [GitHub #535] [GitHub #540]
  • Restore error checks in OpenSSL::PKey::EC#{to_der,to_pem}. [GitHub #541]

Version 3.0.0

Compatibility notes

  • OpenSSL 1.0.1 and Ruby 2.3-2.5 are no longer supported. [GitHub #396] [GitHub #466]

  • OpenSSL 3.0 support is added. It is the first major version bump from OpenSSL 1.1 and contains incompatible changes that affect Ruby/OpenSSL. Note that OpenSSL 3.0 support is preliminary and not all features are currently available: [GitHub #369]

    • Deprecate the ability to modify OpenSSL::PKey::PKey instances. OpenSSL 3.0 made EVP_PKEY structure immutable, and hence the following methods are not available when Ruby/OpenSSL is linked against OpenSSL 3.0. [GitHub #480]

      • OpenSSL::PKey::RSA#set_key, #set_factors, #set_crt_params
      • OpenSSL::PKey::DSA#set_pqg, #set_key
      • OpenSSL::PKey::DH#set_pqg, #set_key, #generate_key!
      • OpenSSL::PKey::EC#private_key=, #public_key=, #group=, #generate_key!

    • Deprecate OpenSSL::Engine. The ENGINE API has been deprecated in OpenSSL 3.0 in favor of the new "provider" concept and will be removed in a future version. [GitHub #481]

  • OpenSSL::SSL::SSLContext#tmp_ecdh_callback has been removed. It has been deprecated since v2.0.0 because it is incompatible with modern OpenSSL versions. [GitHub #394]

  • OpenSSL::SSL::SSLSocket#read and #write now raise OpenSSL::SSL::SSLError if called before a TLS connection is established. Historically, they read/wrote unencrypted data to the underlying socket directly in that case. [GitHub #9] [GitHub #469]

Notable changes

  • Enhance OpenSSL::PKey's common interface. [GitHub #370]

    • Key deserialization: Enhance OpenSSL::PKey.read to handle PEM encoding of DH parameters, which used to be only deserialized by OpenSSL::PKey::DH.new. [GitHub #328]
    • Key generation: Add OpenSSL::PKey.generate_parameters and OpenSSL::PKey.generate_key. [GitHub #329]
    • Public key signing: Enhance OpenSSL::PKey::PKey#sign and #verify to use the new EVP_DigestSign() family to enable PureEdDSA support on OpenSSL 1.1.1 or later. They also now take optional algorithm-specific parameters for more control. [GitHub #329]
    • Low-level public key signing and verification: Add OpenSSL::PKey::PKey#sign_raw, #verify_raw, and #verify_recover. [GitHub #382]
    • Public key encryption: Add OpenSSL::PKey::PKey#encrypt and #decrypt. [GitHub #382]
    • Key agreement: Add OpenSSL::PKey::PKey#derive. [GitHub #329]
    • Key comparison: Add OpenSSL::PKey::PKey#compare? to conveniently check that two keys have common parameters and a public key. [GitHub #383]

  • Add OpenSSL::BN#set_flags and #get_flags. This can be used in combination with OpenSSL::BN::CONSTTIME to force constant-time computation. [GitHub #417]

  • Add OpenSSL::BN#abs to get the absolute value of the BIGNUM. [GitHub #430]

  • Add OpenSSL::SSL::SSLSocket#getbyte. [GitHub #438]

  • Add OpenSSL::SSL::SSLContext#tmp_dh=. [GitHub #459]

  • Add OpenSSL::X509::Certificate.load to load a PEM-encoded and concatenated list of X.509 certificates at once. [GitHub #441]

  • Change OpenSSL::X509::Certificate.new to attempt to deserialize the given string first as DER encoding first and then as PEM encoding to ensure the round-trip consistency. [GitHub #442]

  • Update various part of the code base to use the modern API. No breaking changes are intended with this. This includes:

Version 2.2.3

Bug fixes

  • Fix serveral methods in OpenSSL::PKey::EC::Point attempting to raise an error with an incorrect class, which would end up with a TypeError. [GitHub #570]
  • Fix OpenSSL::PKey::EC::Point#eql? and OpenSSL::PKey::EC::Group#eql? incorrectly treated OpenSSL's internal errors as "not equal". [GitHub #564]
  • Fix build with LibreSSL 3.5 or later.

Version 2.2.2

Merged changes in 2.1.4.

Version 2.2.1

Merged changes in 2.1.3. Additionally, the following issues are fixed by this release.

Bug fixes

  • Fix crash in OpenSSL::Timestamp::{Request,Response,TokenInfo}.new when invalid arguments are given. [GitHub #407]
  • Fix OpenSSL::Timestamp::Factory#create_timestamp with LibreSSL on platforms where time_t has a different size from long. [GitHub #454]

Version 2.2.0

Compatibility notes

  • Remove unsupported MDC2, DSS, DSS1, and SHA algorithms.
  • Remove OpenSSL::PKCS7::SignerInfo#name alias for #issuer. [GitHub #266]
  • Deprecate OpenSSL::Config#add_value and #[]= for future removal. [GitHub #322]

Notable changes

  • Change default OpenSSL::SSL::SSLServer#listen backlog argument from 5 to Socket::SOMAXCONN. [GitHub #286]
  • Make OpenSSL::HMAC#== use a timing safe string comparison. [GitHub #284]
  • Add support for SHA3 and BLAKE digests. [GitHub #282]
  • Add OpenSSL::SSL::SSLSocket.open for opening a TCPSocket and returning an OpenSSL::SSL::SSLSocket for it. [GitHub #225]
  • Support marshalling of OpenSSL::X509 and OpenSSL::PKey objects. [GitHub #281] [GitHub #363]
  • Add OpenSSL.secure_compare for timing safe string comparison for strings of possibly unequal length. [GitHub #280]
  • Add OpenSSL.fixed_length_secure_compare for timing safe string comparison for strings of equal length. [GitHub #269]
  • Add OpenSSL::SSL::SSLSocket#{finished_message,peer_finished_message} for last finished message sent and received. [GitHub #250]
  • Add OpenSSL::Timestamp module for handing timestamp requests and responses. [GitHub #204]
  • Add helper methods for OpenSSL::X509::Certificate: find_extension, subject_key_identifier, authority_key_identifier, crl_uris, ca_issuer_uris and ocsp_uris, and for OpenSSL::X509::CRL: find_extension and subject_key_identifier. [GitHub #260] [GitHub #275] [GitHub #293]
  • Add OpenSSL::ECPoint#add for performing elliptic curve point addition. [GitHub #261]
  • Make OpenSSL::PKey::RSA#{export,to_der} check key, factors, and crt_params to do proper private key serialization. [GitHub #258]
  • Add OpenSSL::SSL::{SSLSocket,SSLServer}#fileno, returning the underlying socket file descriptor number. [GitHub #247]
  • Support client certificates with TLS 1.3, and support post-handshake authentication with OpenSSL 1.1.1+. [GitHub #239]
  • Add OpenSSL::ASN1::ObjectId#== for equality testing.
  • Add OpenSSL::X509::Extension#value_der for the raw value of the extension. [GitHub #234]
  • Significantly reduce allocated memory in OpenSSL::Buffering#do_write. [GitHub #212]
  • Ensure all valid IPv6 addresses are considered valid as elements of subjectAlternativeName in certificates. [GitHub #185]
  • Allow recipient's certificate to be omitted in PCKS7#decrypt. [GitHub #183]
  • Add support for reading keys in PKCS #8 format and export via instance methods added to OpenSSL::PKey classes: private_to_der, private_to_pem, public_to_der and public_to_pem. [GitHub #297]

Version 2.1.4

Bug fixes

  • Do not use pkg-config if --with-openssl-dir option is specified. [GitHub #486]

Version 2.1.3

Bug fixes

  • Fix deprecation warnings on Ruby 3.0.
  • Add ".include" directive support in OpenSSL::Config. [GitHub #216]
  • Fix handling of IPv6 address SANs. [GitHub #185]
  • Hostname verification failure with OpenSSL::SSL::SSLContext#verify_hostname= sets a proper error code. [GitHub #350]
  • Fix crash with OpenSSL::BN.new(nil, 2). [Bug #15760]
  • OpenSSL::SSL::SSLSocket#sys{read,write} prevent internal string buffers from being modified by another thread. [GitHub #453]
  • Fix misuse of input record separator in OpenSSL::Buffering where it was for output.
  • Fix wrong integer casting in OpenSSL::PKey::EC#dsa_verify_asn1. [GitHub #460]
  • extconf.rb explicitly checks that OpenSSL's version number is 1.0.1 or newer but also less than 3.0. Ruby/OpenSSL v2.1.x and v2.2.x will not support OpenSSL 3.0 API. [GitHub #458]
  • Activate digest gem correctly. digest library could go into an inconsistent state if there are multiple versions of digest is installed and openssl is required before digest. [GitHub #463]
  • Fix GC.compact compatibility. [GitHub #464] [GitHub #465]

Version 2.1.2

Merged changes in 2.0.9.

Version 2.1.1

Merged changes in 2.0.8.

Version 2.1.0

Notable changes

  • Support for OpenSSL versions before 1.0.1 and LibreSSL versions before 2.5 is removed. [GitHub #86]
  • OpenSSL::BN#negative?, #+@, and #-@ are added.
  • OpenSSL::SSL::SSLSocket#connect raises a more informative exception when certificate verification fails. [GitHub #99]
  • OpenSSL::KDF module is newly added. In addition to PBKDF2-HMAC that has moved from OpenSSL::PKCS5, scrypt and HKDF are supported. [GitHub #109] [GitHub #173]
  • OpenSSL.fips_mode is added. We had the setter, but not the getter. [GitHub #125]
  • OpenSSL::OCSP::Request#signed? is added.
  • OpenSSL::ASN1 handles the indefinite length form better. OpenSSL::ASN1.decode no longer wrongly treats the end-of-contents octets as part of the content. OpenSSL::ASN1::ASN1Data#infinite_length is renamed to #indefinite_length. [GitHub #98]
  • OpenSSL::X509::Name#add_entry now accepts two additional keyword arguments 'loc' and 'set'. [GitHub #94]
  • OpenSSL::SSL::SSLContext#min_version= and #max_version= are added to replace #ssl_version= that was built on top of the deprecated OpenSSL C API. Use of that method and the constant OpenSSL::SSL::SSLContext::METHODS is now deprecated. [GitHub #142]
  • OpenSSL::X509::Name#to_utf8 is added. [GitHub #26] [GitHub #143]
  • OpenSSL::X509::{Extension,Attribute,Certificate,CRL,Revoked,Request} can be compared with == operator. [GitHub #161]
  • TLS Fallback Signaling Cipher Suite Value (SCSV) support is added. [GitHub #165]
  • Build failure with OpenSSL 1.1 built with no-deprecated is fixed. [GitHub #160]
  • OpenSSL::Buffering#write accepts an arbitrary number of arguments. [Feature #9323] [GitHub #162]
  • OpenSSL::PKey::RSA#sign_pss and #verify_pss are added. They perform RSA-PSS signature and verification. [GitHub #75] [GitHub #76] [GitHub #169]
  • OpenSSL::SSL::SSLContext#add_certificate is added. [GitHub #167]
  • OpenSSL::PKey::EC::Point#to_octet_string is added. OpenSSL::PKey::EC::Point.new can now take String as the second argument. [GitHub #177]

Version 2.0.9

Security fixes

Bug fixes

Version 2.0.8

Bug fixes

Version 2.0.7

Bug fixes

  • OpenSSL::Cipher#auth_data= could segfault if called against a non-AEAD cipher. [Bug #14024]
  • OpenSSL::X509::Certificate#public_key= (and similar methods) could segfault when an instance of OpenSSL::PKey::PKey with no public key components is passed. [Bug #14087] [GitHub #168]

Version 2.0.6

Bug fixes

  • The session_remove_cb set to an OpenSSL::SSL::SSLContext is no longer called during GC.
  • A possible deadlock in OpenSSL::SSL::SSLSocket#sysread is fixed. [GitHub #139]
  • OpenSSL::BN#hash could return an unnormalized fixnum value on Windows. [Bug #13877]
  • OpenSSL::SSL::SSLSocket#sysread and #sysread_nonblock set the length of the destination buffer String to 0 on error. [GitHub #153]
  • Possible deadlock is fixed. This happened only when built with older versions of OpenSSL (before 1.1.0) or LibreSSL. [GitHub #155]

Version 2.0.5

Bug fixes

  • Reading a PEM/DER-encoded private key or certificate from an IO object did not work properly on mswin platforms. [ruby/openssl#128]
  • Broken length check in the PEM passphrase callback is fixed.
  • It failed to compile when OpenSSL is configured without TLS 1.0 support.

Version 2.0.4

Bug fixes

  • It now compiles with LibreSSL without renaming on Windows (mswin).
  • A workaround for the error queue leak of X509_load_cert_crl_file() that causes random errors is added. [Bug #11033]

Version 2.0.3

Bug fixes

  • OpenSSL::ASN1::Constructive#each which was broken by 2.0.0 is fixed. [ruby/openssl#96]
  • Fixed build with static OpenSSL libraries on Windows. [Bug #13080]
  • OpenSSL::X509::Name#eql? which was broken by 2.0.0 is fixed.

Version 2.0.2

Bug fixes

  • Fix build with early 0.9.8 series which did not have SSL_CTX_clear_options(). [ruby-core:78693]

Version 2.0.1

Bug fixes

Version 2.0.0

This is the first release of openssl gem, formerly a standard library of Ruby, ext/openssl. This is the successor of the version included in Ruby 2.3.

Compatibility notes

  • Support for OpenSSL version 0.9.6 and 0.9.7 is completely removed. openssl gem still works with OpenSSL 0.9.8, but users are strongly encouraged to upgrade to at least 1.0.1, as OpenSSL < 1.0.1 will not receive any security fixes from the OpenSSL development team.

Supported platforms

  • OpenSSL 1.0.0, 1.0.1, 1.0.2, 1.1.0
  • OpenSSL < 0.9.8 is no longer supported.
  • LibreSSL 2.3, 2.4, 2.5
  • Ruby 2.3, 2.4

Notable changes

  • Add support for OpenSSL 1.1.0. [Feature #12324]

  • Add support for LibreSSL

  • OpenSSL::Cipher

    • OpenSSL::Cipher#key= and #iv= reject too long inputs. They used to truncate silently. [Bug #12561]

    • OpenSSL::Cipher#iv_len= is added. It allows changing IV (nonce) length if using AEAD ciphers. [Bug #8667], [Bug #10420], [GH ruby/ruby#569], [GH ruby/openssl#58]

    • OpenSSL::Cipher#auth_tag_len= is added. This sets the authentication tag length to be generated by an AEAD cipher.

  • OpenSSL::OCSP

    • Accessor methods are added to OpenSSL::OCSP::CertificateId. [Feature #7181]

    • OpenSSL::OCSP::Request and BasicResponse can be signed with non-SHA-1 hash algorithm. [Feature #11552]

    • OpenSSL::OCSP::CertificateId and BasicResponse can be encoded into DER.

    • A new class OpenSSL::OCSP::SingleResponse is added for convenience.

    • OpenSSL::OCSP::BasicResponse#add_status accepts absolute times. They used to accept only relative seconds from the current time.

  • OpenSSL::PKey

    • OpenSSL::PKey::EC follows the general PKey interface. [Bug #6567]

    • OpenSSL::PKey.read raises OpenSSL::PKey::PKeyError instead of ArgumentError for consistency with OpenSSL::PKey::{DH,DSA,RSA,EC}#new. [Bug #11774], [GH ruby/openssl#55]

    • OpenSSL::PKey::EC::Group retrieved by OpenSSL::PKey::EC#group is no longer linked with the EC key. Modifications to the EC::Group have no effect on the key. [GH ruby/openssl#71]

    • OpenSSL::PKey::EC::Point#to_bn allows specifying the point conversion form by the optional argument.

  • OpenSSL::SSL

    • OpenSSL::SSL::SSLSocket#tmp_key is added. A client can call it after the connection is established to retrieve the ephemeral key. [GH ruby/ruby#1318]

    • The automatic ephemeral ECDH curve selection is enabled by default when built with OpenSSL >= 1.0.2 or LibreSSL.

    • OpenSSL::SSL::SSLContext#security_level= is added. You can set the "security level" of the SSL context. This is effective only when built with OpenSSL 1.1.0.

    • A new option 'verify_hostname' is added to OpenSSL::SSL::SSLContext. When it is enabled, and the SNI hostname is also set, the hostname verification on the server certificate is automatically performed. It is now enabled by OpenSSL::SSL::SSLContext#set_params. [GH ruby/openssl#60]

Removals

  • OpenSSL::Engine

    • OpenSSL::Engine.cleanup does nothing when built with OpenSSL 1.1.0.

  • OpenSSL::SSL

    • OpenSSL::PKey::DH::DEFAULT_512 is removed. Hence servers no longer use 512-bit DH group by default. It is considered too weak nowadays. [Bug #11968], [GH ruby/ruby#1196]

    • RC4 cipher suites are removed from OpenSSL::SSL::SSLContext::DEFAULT_PARAMS. RC4 is now considered to be weak. [GH ruby/openssl#50]

Deprecations

  • OpenSSL::PKey

    • OpenSSL::PKey::RSA#n=, #e=, #d=, #p=, #q=, #dmp1=, #dmq1=, #iqmp=, OpenSSL::PKey::DSA#p=, #q=, #g=, #priv_key=, #pub_key=, OpenSSL::PKey::DH#p=, #g=, #priv_key= and #pub_key= are deprecated. They are disabled when built with OpenSSL 1.1.0, due to its API change. Instead, OpenSSL::PKey::RSA#set_key, #set_factors, #set_crt_params, OpenSSL::PKey::DSA#set_pqg, #set_key, OpenSSL::PKey::DH#set_pqg and #set_key are added.

  • OpenSSL::Random

    • OpenSSL::Random.pseudo_bytes is deprecated, and not defined when built with OpenSSL 1.1.0. Use OpenSSL::Random.random_bytes instead.

  • OpenSSL::SSL

    • OpenSSL::SSL::SSLContext#tmp_ecdh_callback is deprecated, as the underlying API SSL_CTX_set_tmp_ecdh_callback() is removed in OpenSSL 1.1.0. It was first added in Ruby 2.3.0. To specify the curve to be used in ephemeral ECDH, use OpenSSL::SSL::SSLContext#ecdh_curves=. The automatic curve selection is also now enabled by default when built with a capable OpenSSL.