https://github.com/ruby/openssl/commit/d07183f639

Check that OpenSSL::PKey::EC.builtin_curves returns an array in the
expected format.

Similarly to OpenSSL::Cipher.ciphers, OpenSSL::PKey::EC.builtin_curves
returns a list of known named curves rather than actually usable ones.

https://github.com/ruby/openssl/issues/671 found that the list may
include unapproved (and thus unusable) curves when the FIPS module is
loaded.

https://github.com/ruby/openssl/commit/c53cbabe00

(https://github.com/ruby/openssl/pull/586)

String#unpack1 avoids the intermediate array created by String#unpack
for single elements, while also making a call to Array#first/[0]
unnecessary.

https://github.com/ruby/openssl/commit/8eb0715a42

The behavior of EVP_PKEY_public_check changed between OpenSSL 1.1.1
and 3.0 so that it no longer validates the private key. Instead, private
keys can be validated through EVP_PKEY_private_check and
EVP_PKEY_pairwise_check.

[ky: simplified condition to use either EVP_PKEY_check() or
EVP_PKEY_public_check().]

https://github.com/ruby/openssl/commit/e38a63ab3d

Systems such as RHEL 9 are moving away from SHA1
disabling it completely in default configuration.

https://github.com/ruby/openssl/commit/32648da2f6

i2d_PUBKEY_bio() against an EC_KEY without the public key component
trggers a null dereference.

This is a regression introduced by commit https://github.com/ruby/openssl/commit/56f0d34d63fb ("pkey:
refactor #export/#to_pem and #to_der", 2017-06-14).

Fixes https://github.com/ruby/openssl/pull/527#issuecomment-1220504524
Fixes https://github.com/ruby/openssl/issues/369#issuecomment-1221554057

https://github.com/ruby/openssl/commit/f6ee0fa4de

Scan through the input for a private key, then fallback to generic
decoder.

OpenSSL 3.0's OSSL_DECODER supports encoded key parameters. The PEM
header "-----BEGIN EC PARAMETERS-----" is used by one of such encoding
formats. While this is useful for OpenSSL::PKey::PKey, an edge case has
been discovered.

The openssl CLI command line "openssl ecparam -genkey" prints two PEM
blocks in a row, one for EC parameters and another for the private key.
Feeding the whole output into OSSL_DECODER results in only the first PEM
block, the key parameters, being decoded. Previously, ruby/openssl did
not support decoding key parameters and it would decode the private key
PEM block instead.

While the new behavior is technically correct, "openssl ecparam -genkey"
is so widely used that ruby/openssl does not want to break existing
applications.

Fixes https://github.com/ruby/openssl/pull/535

https://github.com/ruby/openssl/commit/d486c82833

OpenSSL 3.0 made EVP_PKEY immutable. This means we can only have a const
pointer of the low level struct and the following methods can no longer
be provided when linked against OpenSSL 3.0:

 - OpenSSL::PKey::RSA#set_key
 - OpenSSL::PKey::RSA#set_factors
 - OpenSSL::PKey::RSA#set_crt_params
 - OpenSSL::PKey::DSA#set_pqg
 - OpenSSL::PKey::DSA#set_key
 - OpenSSL::PKey::DH#set_pqg
 - OpenSSL::PKey::DH#set_key
 - OpenSSL::PKey::EC#group=
 - OpenSSL::PKey::EC#private_key=
 - OpenSSL::PKey::EC#public_key=

There is no direct replacement for this functionality at the moment.
I plan to introduce a wrapper around EVP_PKEY_fromdata(), which takes
all key components at once to construct an EVP_PKEY.

https://github.com/ruby/openssl/commit/6848d2d969

OpenSSL::PKey::EC#generate_key! will not work on OpenSSL 3.0 because
keys are made immutable. Users should use OpenSSL::PKey.generate_key
instead.

https://github.com/ruby/openssl/commit/5e2e66cce8

Disabling ECC support of OpenSSL is impractical nowadays.

We still try to have the C extension compile on no-ec builds (as well
as no-dh or no-engine, etc.) as long as we can, but keeping test cases
for such an extreme scenario is not worth the effort.

https://github.com/ruby/openssl/commit/2cd01d4676