Package: release.debian.org
Severity: normal
User: release.debian....@packages.debian.org
Usertags: unblock
X-Debbugs-Cc: ruby...@packages.debian.org
Control: affects -1 + src:ruby3.1

Please unblock package ruby3.1

[ Reason ]
This release updates the openssl bindings, fixing a few regressions that
have been identified.

[ Impact ]
Without these changes, at least gitlab doesn't work correctly.

[ Tests ]
I had uploaded this to experimental some time ago, and the pseudo
excuses against unstable showed no regressions.

[ Risks ]
The changes are contained to the implementatin of a few openssl methods.
I think the risk is low. I had also tried updating to the new upstream
release 3.1.3, which includes this change, but thought that contained
too many non-critical changes.

[ Checklist ]
  [x] all changes are documented in the d/changelog
  [x] I reviewed all changes and I approve them
  [x] attach debdiff against the package in testing

[ Other info ]
I'm also attaching the actual patch included in this upload as it is
easier to read than the diff-in-diff in the debdiff.

unblock ruby3.1/3.1.2-7
diff --git a/debian/changelog b/debian/changelog
index c6bd035fc..54e474d21 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,15 @@
+ruby3.1 (3.1.2-7) unstable; urgency=medium
+
+  * Upload to unstable
+
+ -- Antonio Terceiro <terce...@debian.org>  Sat, 25 Mar 2023 14:20:34 -0300
+
+ruby3.1 (3.1.2-7~exp) experimental; urgency=medium
+
+  * Update openssl extension to to 3.0.1 (Closes: #1032070)
+
+ -- Antonio Terceiro <terce...@debian.org>  Sun, 05 Mar 2023 17:13:36 -0300
+
 ruby3.1 (3.1.2-6) unstable; urgency=medium
 
   * Add missing dependencies for pkg-config test
diff --git a/debian/patches/openssl-3.0.1.patch b/debian/patches/openssl-3.0.1.patch
new file mode 100644
index 000000000..0762cb65e
--- /dev/null
+++ b/debian/patches/openssl-3.0.1.patch
@@ -0,0 +1,495 @@
+From: Antonio Terceiro <terce...@debian.org>
+Date: Sun, 5 Mar 2023 17:09:05 -0300
+Subject: openssl 3.0.1
+
+This is a combination of several patches for openssl extension that fix
+bugs in its version 3.0.0.
+
+Forwarded: not-needed
+---
+ ext/openssl/History.md             | 40 +++++++++++++++++++++++++++++++++
+ ext/openssl/extconf.rb             |  5 +++--
+ ext/openssl/lib/openssl/pkey.rb    |  8 +++++++
+ ext/openssl/lib/openssl/version.rb |  2 +-
+ ext/openssl/openssl.gemspec        |  2 +-
+ ext/openssl/ossl_hmac.c            |  8 +++++++
+ ext/openssl/ossl_pkey.c            | 46 +++++++++++++++++++++++++++++++++++---
+ ext/openssl/ossl_pkey_ec.c         |  4 ++++
+ ext/openssl/ossl_x509cert.c        |  6 ++---
+ ext/openssl/ossl_x509crl.c         |  6 ++---
+ ext/openssl/ossl_x509req.c         |  6 ++---
+ ext/openssl/ossl_x509revoked.c     |  6 ++---
+ test/openssl/test_hmac.rb          |  8 +++++++
+ test/openssl/test_pkey_dsa.rb      | 19 ++++++++++++++++
+ test/openssl/test_pkey_ec.rb       | 25 +++++++++++++++++++++
+ test/openssl/test_pkey_rsa.rb      |  5 +++++
+ test/openssl/test_ssl.rb           |  6 +++++
+ 17 files changed, 183 insertions(+), 19 deletions(-)
+
+diff --git a/ext/openssl/History.md b/ext/openssl/History.md
+index 479ec3b..a4f6bd7 100644
+--- a/ext/openssl/History.md
++++ b/ext/openssl/History.md
+@@ -1,3 +1,27 @@
++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]](https://github.com/ruby/openssl/pull/531)
++* Work around OpenSSL 3.0's HMAC issues with a zero-length key.
++  [[GitHub #538]](https://github.com/ruby/openssl/pull/538)
++* Fix a regression in OpenSSL::PKey::DSA.generate's default of 'q' size.
++  [[GitHub #483]](https://github.com/ruby/openssl/issues/483)
++  [[GitHub #539]](https://github.com/ruby/openssl/pull/539)
++* Restore OpenSSL::PKey.read's ability to decode "openssl ecparam -genkey"
++  output when linked against OpenSSL 3.0.
++  [[GitHub #535]](https://github.com/ruby/openssl/pull/535)
++  [[GitHub #540]](https://github.com/ruby/openssl/pull/540)
++* Restore error checks in OpenSSL::PKey::EC#{to_der,to_pem}.
++  [[GitHub #541]](https://github.com/ruby/openssl/pull/541)
++
++
+ Version 3.0.0
+ =============
+ 
+@@ -100,6 +124,12 @@ Notable changes
+     [[GitHub #342]](https://github.com/ruby/openssl/issues/342)
+ 
+ 
++Version 2.2.2
++=============
++
++Merged changes in 2.1.4.
++
++
+ Version 2.2.1
+ =============
+ 
+@@ -194,6 +224,16 @@ Notable changes
+   [[GitHub #297]](https://github.com/ruby/openssl/pull/297)
+ 
+ 
++Version 2.1.4
++=============
++
++Bug fixes
++---------
++
++* Do not use pkg-config if --with-openssl-dir option is specified.
++ [[GitHub #486]](https://github.com/ruby/openssl/pull/486)
++
++
+ Version 2.1.3
+ =============
+ 
+diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
+index fedcb93..d2d7893 100644
+--- a/ext/openssl/extconf.rb
++++ b/ext/openssl/extconf.rb
+@@ -13,7 +13,7 @@
+ 
+ require "mkmf"
+ 
+-dir_config("openssl")
++dir_config_given = dir_config("openssl").any?
+ dir_config("kerberos")
+ 
+ Logging::message "=== OpenSSL for Ruby configurator ===\n"
+@@ -92,7 +92,7 @@ def find_openssl_library
+ end
+ 
+ Logging::message "=== Checking for required stuff... ===\n"
+-pkg_config_found = pkg_config("openssl") && have_header("openssl/ssl.h")
++pkg_config_found = !dir_config_given && pkg_config("openssl") && have_header("openssl/ssl.h")
+ 
+ if !pkg_config_found && !find_openssl_library
+   Logging::message "=== Checking for required stuff failed. ===\n"
+@@ -169,6 +169,7 @@ have_func("SSL_CTX_set_post_handshake_auth")
+ 
+ # added in 1.1.1
+ have_func("EVP_PKEY_check")
++have_func("EVP_PKEY_new_raw_private_key")
+ 
+ # added in 3.0.0
+ have_func("SSL_set0_tmp_dh_pkey")
+diff --git a/ext/openssl/lib/openssl/pkey.rb b/ext/openssl/lib/openssl/pkey.rb
+index c3e0629..d51f066 100644
+--- a/ext/openssl/lib/openssl/pkey.rb
++++ b/ext/openssl/lib/openssl/pkey.rb
+@@ -167,8 +167,16 @@ module OpenSSL::PKey
+       # +size+::
+       #   The desired key size in bits.
+       def generate(size, &blk)
++        # FIPS 186-4 specifies four (L,N) pairs: (1024,160), (2048,224),
++        # (2048,256), and (3072,256).
++        #
++        # q size is derived here with compatibility with
++        # DSA_generator_parameters_ex() which previous versions of ruby/openssl
++        # used to call.
++        qsize = size >= 2048 ? 256 : 160
+         dsaparams = OpenSSL::PKey.generate_parameters("DSA", {
+           "dsa_paramgen_bits" => size,
++          "dsa_paramgen_q_bits" => qsize,
+         }, &blk)
+         OpenSSL::PKey.generate_key(dsaparams)
+       end
+diff --git a/ext/openssl/lib/openssl/version.rb b/ext/openssl/lib/openssl/version.rb
+index 5e60604..b9e8444 100644
+--- a/ext/openssl/lib/openssl/version.rb
++++ b/ext/openssl/lib/openssl/version.rb
+@@ -1,5 +1,5 @@
+ # frozen_string_literal: true
+ 
+ module OpenSSL
+-  VERSION = "3.0.0"
++  VERSION = "3.0.1"
+ end
+diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
+index c6cd818..1c13505 100644
+--- a/ext/openssl/openssl.gemspec
++++ b/ext/openssl/openssl.gemspec
+@@ -1,6 +1,6 @@
+ Gem::Specification.new do |spec|
+   spec.name          = "openssl"
+-  spec.version       = "3.0.0"
++  spec.version       = "3.0.1"
+   spec.authors       = ["Martin Bosslet", "SHIBATA Hiroshi", "Zachary Scott", "Kazuki Yamaguchi"]
+   spec.email         = ["ruby-c...@ruby-lang.org"]
+   spec.summary       = %q{OpenSSL provides SSL, TLS and general purpose cryptography.}
+diff --git a/ext/openssl/ossl_hmac.c b/ext/openssl/ossl_hmac.c
+index bfe3a74..1a5f471 100644
+--- a/ext/openssl/ossl_hmac.c
++++ b/ext/openssl/ossl_hmac.c
+@@ -97,11 +97,19 @@ ossl_hmac_initialize(VALUE self, VALUE key, VALUE digest)
+ 
+     GetHMAC(self, ctx);
+     StringValue(key);
++#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
++    pkey = EVP_PKEY_new_raw_private_key(EVP_PKEY_HMAC, NULL,
++                                        (unsigned char *)RSTRING_PTR(key),
++                                        RSTRING_LENINT(key));
++    if (!pkey)
++        ossl_raise(eHMACError, "EVP_PKEY_new_raw_private_key");
++#else
+     pkey = EVP_PKEY_new_mac_key(EVP_PKEY_HMAC, NULL,
+                                 (unsigned char *)RSTRING_PTR(key),
+                                 RSTRING_LENINT(key));
+     if (!pkey)
+         ossl_raise(eHMACError, "EVP_PKEY_new_mac_key");
++#endif
+     if (EVP_DigestSignInit(ctx, NULL, ossl_evp_get_digestbyname(digest),
+                            NULL, pkey) != 1) {
+         EVP_PKEY_free(pkey);
+diff --git a/ext/openssl/ossl_pkey.c b/ext/openssl/ossl_pkey.c
+index 2a4835a..ee143d6 100644
+--- a/ext/openssl/ossl_pkey.c
++++ b/ext/openssl/ossl_pkey.c
+@@ -99,17 +99,56 @@ ossl_pkey_read_generic(BIO *bio, VALUE pass)
+     /* First check DER */
+     if (OSSL_DECODER_from_bio(dctx, bio) == 1)
+         goto out;
++    OSSL_BIO_reset(bio);
+ 
+     /* Then check PEM; multiple OSSL_DECODER_from_bio() calls may be needed */
+-    OSSL_BIO_reset(bio);
+     if (OSSL_DECODER_CTX_set_input_type(dctx, "PEM") != 1)
+         goto out;
+-    while (OSSL_DECODER_from_bio(dctx, bio) != 1) {
+-        if (BIO_eof(bio))
++    /*
++     * First check for private key formats. This is to keep compatibility with
++     * ruby/openssl < 3.0 which decoded the following as a private key.
++     *
++     *     $ openssl ecparam -name prime256v1 -genkey -outform PEM
++     *     -----BEGIN EC PARAMETERS-----
++     *     BggqhkjOPQMBBw==
++     *     -----END EC PARAMETERS-----
++     *     -----BEGIN EC PRIVATE KEY-----
++     *     MHcCAQEEIAG8ugBbA5MHkqnZ9ujQF93OyUfL9tk8sxqM5Wv5tKg5oAoGCCqGSM49
++     *     AwEHoUQDQgAEVcjhJfkwqh5C7kGuhAf8XaAjVuG5ADwb5ayg/cJijCgs+GcXeedj
++     *     86avKpGH84DXUlB23C/kPt+6fXYlitUmXQ==
++     *     -----END EC PRIVATE KEY-----
++     *
++     * While the first PEM block is a proper encoding of ECParameters, thus
++     * OSSL_DECODER_from_bio() would pick it up, ruby/openssl used to return
++     * the latter instead. Existing applications expect this behavior.
++     *
++     * Note that normally, the input is supposed to contain a single decodable
++     * PEM block only, so this special handling should not create a new problem.
++     */
++    OSSL_DECODER_CTX_set_selection(dctx, EVP_PKEY_KEYPAIR);
++    while (1) {
++        if (OSSL_DECODER_from_bio(dctx, bio) == 1)
+             goto out;
++        if (BIO_eof(bio))
++            break;
+         pos2 = BIO_tell(bio);
+         if (pos2 < 0 || pos2 <= pos)
++            break;
++        ossl_clear_error();
++        pos = pos2;
++    }
++
++    OSSL_BIO_reset(bio);
++    OSSL_DECODER_CTX_set_selection(dctx, 0);
++    while (1) {
++        if (OSSL_DECODER_from_bio(dctx, bio) == 1)
+             goto out;
++        if (BIO_eof(bio))
++            break;
++        pos2 = BIO_tell(bio);
++        if (pos2 < 0 || pos2 <= pos)
++            break;
++        ossl_clear_error();
+         pos = pos2;
+     }
+ 
+@@ -200,6 +239,7 @@ static VALUE
+ pkey_ctx_apply_options0(VALUE args_v)
+ {
+     VALUE *args = (VALUE *)args_v;
++    Check_Type(args[1], T_HASH);
+ 
+     rb_block_call(args[1], rb_intern("each"), 0, NULL,
+                   pkey_ctx_apply_options_i, args[0]);
+diff --git a/ext/openssl/ossl_pkey_ec.c b/ext/openssl/ossl_pkey_ec.c
+index dee2154..06d59c2 100644
+--- a/ext/openssl/ossl_pkey_ec.c
++++ b/ext/openssl/ossl_pkey_ec.c
+@@ -414,6 +414,8 @@ ossl_ec_key_export(int argc, VALUE *argv, VALUE self)
+     EC_KEY *ec;
+ 
+     GetEC(self, ec);
++    if (EC_KEY_get0_public_key(ec) == NULL)
++        ossl_raise(eECError, "can't export - no public key set");
+     if (EC_KEY_get0_private_key(ec))
+         return ossl_pkey_export_traditional(argc, argv, self, 0);
+     else
+@@ -432,6 +434,8 @@ ossl_ec_key_to_der(VALUE self)
+     EC_KEY *ec;
+ 
+     GetEC(self, ec);
++    if (EC_KEY_get0_public_key(ec) == NULL)
++        ossl_raise(eECError, "can't export - no public key set");
+     if (EC_KEY_get0_private_key(ec))
+         return ossl_pkey_export_traditional(0, NULL, self, 1);
+     else
+diff --git a/ext/openssl/ossl_x509cert.c b/ext/openssl/ossl_x509cert.c
+index 996f184..9443541 100644
+--- a/ext/openssl/ossl_x509cert.c
++++ b/ext/openssl/ossl_x509cert.c
+@@ -642,12 +642,12 @@ ossl_x509_set_extensions(VALUE self, VALUE ary)
+ 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
+     }
+     GetX509(self, x509);
+-    while ((ext = X509_delete_ext(x509, 0)))
+-	X509_EXTENSION_free(ext);
++    for (i = X509_get_ext_count(x509); i > 0; i--)
++        X509_EXTENSION_free(X509_delete_ext(x509, 0));
+     for (i=0; i<RARRAY_LEN(ary); i++) {
+ 	ext = GetX509ExtPtr(RARRAY_AREF(ary, i));
+ 	if (!X509_add_ext(x509, ext, -1)) { /* DUPs ext */
+-	    ossl_raise(eX509CertError, NULL);
++	    ossl_raise(eX509CertError, "X509_add_ext");
+ 	}
+     }
+ 
+diff --git a/ext/openssl/ossl_x509crl.c b/ext/openssl/ossl_x509crl.c
+index 863f028..6c1d915 100644
+--- a/ext/openssl/ossl_x509crl.c
++++ b/ext/openssl/ossl_x509crl.c
+@@ -474,12 +474,12 @@ ossl_x509crl_set_extensions(VALUE self, VALUE ary)
+ 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
+     }
+     GetX509CRL(self, crl);
+-    while ((ext = X509_CRL_delete_ext(crl, 0)))
+-	X509_EXTENSION_free(ext);
++    for (i = X509_CRL_get_ext_count(crl); i > 0; i--)
++        X509_EXTENSION_free(X509_CRL_delete_ext(crl, 0));
+     for (i=0; i<RARRAY_LEN(ary); i++) {
+ 	ext = GetX509ExtPtr(RARRAY_AREF(ary, i)); /* NO NEED TO DUP */
+ 	if (!X509_CRL_add_ext(crl, ext, -1)) {
+-	    ossl_raise(eX509CRLError, NULL);
++	    ossl_raise(eX509CRLError, "X509_CRL_add_ext");
+ 	}
+     }
+ 
+diff --git a/ext/openssl/ossl_x509req.c b/ext/openssl/ossl_x509req.c
+index 6eb91e9..77a7d3f 100644
+--- a/ext/openssl/ossl_x509req.c
++++ b/ext/openssl/ossl_x509req.c
+@@ -380,13 +380,13 @@ ossl_x509req_set_attributes(VALUE self, VALUE ary)
+ 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Attr);
+     }
+     GetX509Req(self, req);
+-    while ((attr = X509_REQ_delete_attr(req, 0)))
+-	X509_ATTRIBUTE_free(attr);
++    for (i = X509_REQ_get_attr_count(req); i > 0; i--)
++        X509_ATTRIBUTE_free(X509_REQ_delete_attr(req, 0));
+     for (i=0;i<RARRAY_LEN(ary); i++) {
+ 	item = RARRAY_AREF(ary, i);
+ 	attr = GetX509AttrPtr(item);
+ 	if (!X509_REQ_add1_attr(req, attr)) {
+-	    ossl_raise(eX509ReqError, NULL);
++	    ossl_raise(eX509ReqError, "X509_REQ_add1_attr");
+ 	}
+     }
+     return ary;
+diff --git a/ext/openssl/ossl_x509revoked.c b/ext/openssl/ossl_x509revoked.c
+index 5fe6853..10b8aa4 100644
+--- a/ext/openssl/ossl_x509revoked.c
++++ b/ext/openssl/ossl_x509revoked.c
+@@ -223,13 +223,13 @@ ossl_x509revoked_set_extensions(VALUE self, VALUE ary)
+ 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
+     }
+     GetX509Rev(self, rev);
+-    while ((ext = X509_REVOKED_delete_ext(rev, 0)))
+-	X509_EXTENSION_free(ext);
++    for (i = X509_REVOKED_get_ext_count(rev); i > 0; i--)
++        X509_EXTENSION_free(X509_REVOKED_delete_ext(rev, 0));
+     for (i=0; i<RARRAY_LEN(ary); i++) {
+ 	item = RARRAY_AREF(ary, i);
+ 	ext = GetX509ExtPtr(item);
+ 	if(!X509_REVOKED_add_ext(rev, ext, -1)) {
+-	    ossl_raise(eX509RevError, NULL);
++	    ossl_raise(eX509RevError, "X509_REVOKED_add_ext");
+ 	}
+     }
+ 
+diff --git a/test/openssl/test_hmac.rb b/test/openssl/test_hmac.rb
+index 47cb371..08b888d 100644
+--- a/test/openssl/test_hmac.rb
++++ b/test/openssl/test_hmac.rb
+@@ -63,6 +63,14 @@ class OpenSSL::TestHMAC < OpenSSL::TestCase
+     b64digest = OpenSSL::HMAC.base64digest("MD5", key, "Hi There")
+     assert_equal "kpRyejY4uxwT9I74FYv8nQ==", b64digest
+   end
++
++  def test_zero_length_key
++    # Empty string as the key
++    hexdigest = OpenSSL::HMAC.hexdigest("SHA256", "\0"*32, "test")
++    assert_equal "43b0cef99265f9e34c10ea9d3501926d27b39f57c6d674561d8ba236e7a819fb", hexdigest
++    hexdigest = OpenSSL::HMAC.hexdigest("SHA256", "", "test")
++    assert_equal "43b0cef99265f9e34c10ea9d3501926d27b39f57c6d674561d8ba236e7a819fb", hexdigest
++  end
+ end
+ 
+ end
+diff --git a/test/openssl/test_pkey_dsa.rb b/test/openssl/test_pkey_dsa.rb
+index 726b7db..de6aa63 100644
+--- a/test/openssl/test_pkey_dsa.rb
++++ b/test/openssl/test_pkey_dsa.rb
+@@ -28,6 +28,25 @@ class OpenSSL::TestPKeyDSA < OpenSSL::PKeyTestCase
+     end
+   end
+ 
++  def test_generate
++    # DSA.generate used to call DSA_generate_parameters_ex(), which adjusts the
++    # size of q according to the size of p
++    key1024 = OpenSSL::PKey::DSA.generate(1024)
++    assert_predicate key1024, :private?
++    assert_equal 1024, key1024.p.num_bits
++    assert_equal 160, key1024.q.num_bits
++
++    key2048 = OpenSSL::PKey::DSA.generate(2048)
++    assert_equal 2048, key2048.p.num_bits
++    assert_equal 256, key2048.q.num_bits
++
++    if ENV["OSSL_TEST_ALL"] == "1" # slow
++      key3072 = OpenSSL::PKey::DSA.generate(3072)
++      assert_equal 3072, key3072.p.num_bits
++      assert_equal 256, key3072.q.num_bits
++    end
++  end
++
+   def test_sign_verify
+     dsa512 = Fixtures.pkey("dsa512")
+     data = "Sign me!"
+diff --git a/test/openssl/test_pkey_ec.rb b/test/openssl/test_pkey_ec.rb
+index ffe5a94..9a4818d 100644
+--- a/test/openssl/test_pkey_ec.rb
++++ b/test/openssl/test_pkey_ec.rb
+@@ -61,8 +61,10 @@ class OpenSSL::TestEC < OpenSSL::PKeyTestCase
+   def test_generate_key
+     ec = OpenSSL::PKey::EC.new("prime256v1")
+     assert_equal false, ec.private?
++    assert_raise(OpenSSL::PKey::ECError) { ec.to_der }
+     ec.generate_key!
+     assert_equal true, ec.private?
++    assert_nothing_raised { ec.to_der }
+   end if !openssl?(3, 0, 0)
+ 
+   def test_marshal
+@@ -199,6 +201,29 @@ class OpenSSL::TestEC < OpenSSL::PKeyTestCase
+     assert_equal pem, p256.export
+   end
+ 
++  def test_ECPrivateKey_with_parameters
++    p256 = Fixtures.pkey("p256")
++
++    # The format used by "openssl ecparam -name prime256v1 -genkey -outform PEM"
++    #
++    # "EC PARAMETERS" block should be ignored if it is followed by an
++    # "EC PRIVATE KEY" block
++    in_pem = <<~EOF
++    -----BEGIN EC PARAMETERS-----
++    BggqhkjOPQMBBw==
++    -----END EC PARAMETERS-----
++    -----BEGIN EC PRIVATE KEY-----
++    MHcCAQEEIID49FDqcf1O1eO8saTgG70UbXQw9Fqwseliit2aWhH1oAoGCCqGSM49
++    AwEHoUQDQgAEFglk2c+oVUIKQ64eZG9bhLNPWB7lSZ/ArK41eGy5wAzU/0G51Xtt
++    CeBUl+MahZtn9fO1JKdF4qJmS39dXnpENg==
++    -----END EC PRIVATE KEY-----
++    EOF
++
++    key = OpenSSL::PKey::EC.new(in_pem)
++    assert_same_ec p256, key
++    assert_equal p256.to_der, key.to_der
++  end
++
+   def test_ECPrivateKey_encrypted
+     p256 = Fixtures.pkey("p256")
+     # key = abcdef
+diff --git a/test/openssl/test_pkey_rsa.rb b/test/openssl/test_pkey_rsa.rb
+index 4bb39ed..fa84b76 100644
+--- a/test/openssl/test_pkey_rsa.rb
++++ b/test/openssl/test_pkey_rsa.rb
+@@ -108,6 +108,11 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
+                                       salt_length: 20, mgf1_hash: "SHA1")
+     # Defaults to PKCS #1 v1.5 padding => verification failure
+     assert_equal false, key.verify("SHA256", sig_pss, data)
++
++    # option type check
++    assert_raise_with_message(TypeError, /expected Hash/) {
++      key.sign("SHA256", data, ["x"])
++    }
+   end
+ 
+   def test_sign_verify_raw
+diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
+index a7607da..39964bf 100644
+--- a/test/openssl/test_ssl.rb
++++ b/test/openssl/test_ssl.rb
+@@ -676,10 +676,16 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
+     #     buzz.example.net, respectively).  ...
+     assert_equal(true, OpenSSL::SSL.verify_certificate_identity(
+       create_cert_with_san('DNS:baz*.example.com'), 'baz1.example.com'))
++
++    # LibreSSL 3.5.0+ doesn't support other wildcard certificates
++    # (it isn't required to, as RFC states MAY, not MUST)
++    return if libressl?(3, 5, 0)
++
+     assert_equal(true, OpenSSL::SSL.verify_certificate_identity(
+       create_cert_with_san('DNS:*baz.example.com'), 'foobaz.example.com'))
+     assert_equal(true, OpenSSL::SSL.verify_certificate_identity(
+       create_cert_with_san('DNS:b*z.example.com'), 'buzz.example.com'))
++
+     # Section 6.4.3 of RFC6125 states that client should NOT match identifier
+     # where wildcard is other than left-most label.
+     #
diff --git a/debian/patches/series b/debian/patches/series
index e2febb232..50eaef8ce 100644
--- a/debian/patches/series
+++ b/debian/patches/series
@@ -14,3 +14,4 @@ Fallback-PKG_CONFIG-to-the-configured-pkg-config-always.patch
 Honor-the-tool-prefix-against-pkg-config.patch
 Fix-for-tzdata-2022g.patch
 Merge-CGI-0.3.5.patch
+openssl-3.0.1.patch
From: Antonio Terceiro <terce...@debian.org>
Date: Sun, 5 Mar 2023 17:09:05 -0300
Subject: openssl 3.0.1

This is a combination of several patches for openssl extension that fix
bugs in its version 3.0.0.

Forwarded: not-needed
---
 ext/openssl/History.md             | 40 +++++++++++++++++++++++++++++++++
 ext/openssl/extconf.rb             |  5 +++--
 ext/openssl/lib/openssl/pkey.rb    |  8 +++++++
 ext/openssl/lib/openssl/version.rb |  2 +-
 ext/openssl/openssl.gemspec        |  2 +-
 ext/openssl/ossl_hmac.c            |  8 +++++++
 ext/openssl/ossl_pkey.c            | 46 +++++++++++++++++++++++++++++++++++---
 ext/openssl/ossl_pkey_ec.c         |  4 ++++
 ext/openssl/ossl_x509cert.c        |  6 ++---
 ext/openssl/ossl_x509crl.c         |  6 ++---
 ext/openssl/ossl_x509req.c         |  6 ++---
 ext/openssl/ossl_x509revoked.c     |  6 ++---
 test/openssl/test_hmac.rb          |  8 +++++++
 test/openssl/test_pkey_dsa.rb      | 19 ++++++++++++++++
 test/openssl/test_pkey_ec.rb       | 25 +++++++++++++++++++++
 test/openssl/test_pkey_rsa.rb      |  5 +++++
 test/openssl/test_ssl.rb           |  6 +++++
 17 files changed, 183 insertions(+), 19 deletions(-)

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index 479ec3b..a4f6bd7 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,3 +1,27 @@
+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]](https://github.com/ruby/openssl/pull/531)
+* Work around OpenSSL 3.0's HMAC issues with a zero-length key.
+  [[GitHub #538]](https://github.com/ruby/openssl/pull/538)
+* Fix a regression in OpenSSL::PKey::DSA.generate's default of 'q' size.
+  [[GitHub #483]](https://github.com/ruby/openssl/issues/483)
+  [[GitHub #539]](https://github.com/ruby/openssl/pull/539)
+* Restore OpenSSL::PKey.read's ability to decode "openssl ecparam -genkey"
+  output when linked against OpenSSL 3.0.
+  [[GitHub #535]](https://github.com/ruby/openssl/pull/535)
+  [[GitHub #540]](https://github.com/ruby/openssl/pull/540)
+* Restore error checks in OpenSSL::PKey::EC#{to_der,to_pem}.
+  [[GitHub #541]](https://github.com/ruby/openssl/pull/541)
+
+
 Version 3.0.0
 =============
 
@@ -100,6 +124,12 @@ Notable changes
     [[GitHub #342]](https://github.com/ruby/openssl/issues/342)
 
 
+Version 2.2.2
+=============
+
+Merged changes in 2.1.4.
+
+
 Version 2.2.1
 =============
 
@@ -194,6 +224,16 @@ Notable changes
   [[GitHub #297]](https://github.com/ruby/openssl/pull/297)
 
 
+Version 2.1.4
+=============
+
+Bug fixes
+---------
+
+* Do not use pkg-config if --with-openssl-dir option is specified.
+ [[GitHub #486]](https://github.com/ruby/openssl/pull/486)
+
+
 Version 2.1.3
 =============
 
diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index fedcb93..d2d7893 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -13,7 +13,7 @@
 
 require "mkmf"
 
-dir_config("openssl")
+dir_config_given = dir_config("openssl").any?
 dir_config("kerberos")
 
 Logging::message "=== OpenSSL for Ruby configurator ===\n"
@@ -92,7 +92,7 @@ def find_openssl_library
 end
 
 Logging::message "=== Checking for required stuff... ===\n"
-pkg_config_found = pkg_config("openssl") && have_header("openssl/ssl.h")
+pkg_config_found = !dir_config_given && pkg_config("openssl") && have_header("openssl/ssl.h")
 
 if !pkg_config_found && !find_openssl_library
   Logging::message "=== Checking for required stuff failed. ===\n"
@@ -169,6 +169,7 @@ have_func("SSL_CTX_set_post_handshake_auth")
 
 # added in 1.1.1
 have_func("EVP_PKEY_check")
+have_func("EVP_PKEY_new_raw_private_key")
 
 # added in 3.0.0
 have_func("SSL_set0_tmp_dh_pkey")
diff --git a/ext/openssl/lib/openssl/pkey.rb b/ext/openssl/lib/openssl/pkey.rb
index c3e0629..d51f066 100644
--- a/ext/openssl/lib/openssl/pkey.rb
+++ b/ext/openssl/lib/openssl/pkey.rb
@@ -167,8 +167,16 @@ module OpenSSL::PKey
       # +size+::
       #   The desired key size in bits.
       def generate(size, &blk)
+        # FIPS 186-4 specifies four (L,N) pairs: (1024,160), (2048,224),
+        # (2048,256), and (3072,256).
+        #
+        # q size is derived here with compatibility with
+        # DSA_generator_parameters_ex() which previous versions of ruby/openssl
+        # used to call.
+        qsize = size >= 2048 ? 256 : 160
         dsaparams = OpenSSL::PKey.generate_parameters("DSA", {
           "dsa_paramgen_bits" => size,
+          "dsa_paramgen_q_bits" => qsize,
         }, &blk)
         OpenSSL::PKey.generate_key(dsaparams)
       end
diff --git a/ext/openssl/lib/openssl/version.rb b/ext/openssl/lib/openssl/version.rb
index 5e60604..b9e8444 100644
--- a/ext/openssl/lib/openssl/version.rb
+++ b/ext/openssl/lib/openssl/version.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
 
 module OpenSSL
-  VERSION = "3.0.0"
+  VERSION = "3.0.1"
 end
diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
index c6cd818..1c13505 100644
--- a/ext/openssl/openssl.gemspec
+++ b/ext/openssl/openssl.gemspec
@@ -1,6 +1,6 @@
 Gem::Specification.new do |spec|
   spec.name          = "openssl"
-  spec.version       = "3.0.0"
+  spec.version       = "3.0.1"
   spec.authors       = ["Martin Bosslet", "SHIBATA Hiroshi", "Zachary Scott", "Kazuki Yamaguchi"]
   spec.email         = ["ruby-c...@ruby-lang.org"]
   spec.summary       = %q{OpenSSL provides SSL, TLS and general purpose cryptography.}
diff --git a/ext/openssl/ossl_hmac.c b/ext/openssl/ossl_hmac.c
index bfe3a74..1a5f471 100644
--- a/ext/openssl/ossl_hmac.c
+++ b/ext/openssl/ossl_hmac.c
@@ -97,11 +97,19 @@ ossl_hmac_initialize(VALUE self, VALUE key, VALUE digest)
 
     GetHMAC(self, ctx);
     StringValue(key);
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+    pkey = EVP_PKEY_new_raw_private_key(EVP_PKEY_HMAC, NULL,
+                                        (unsigned char *)RSTRING_PTR(key),
+                                        RSTRING_LENINT(key));
+    if (!pkey)
+        ossl_raise(eHMACError, "EVP_PKEY_new_raw_private_key");
+#else
     pkey = EVP_PKEY_new_mac_key(EVP_PKEY_HMAC, NULL,
                                 (unsigned char *)RSTRING_PTR(key),
                                 RSTRING_LENINT(key));
     if (!pkey)
         ossl_raise(eHMACError, "EVP_PKEY_new_mac_key");
+#endif
     if (EVP_DigestSignInit(ctx, NULL, ossl_evp_get_digestbyname(digest),
                            NULL, pkey) != 1) {
         EVP_PKEY_free(pkey);
diff --git a/ext/openssl/ossl_pkey.c b/ext/openssl/ossl_pkey.c
index 2a4835a..ee143d6 100644
--- a/ext/openssl/ossl_pkey.c
+++ b/ext/openssl/ossl_pkey.c
@@ -99,17 +99,56 @@ ossl_pkey_read_generic(BIO *bio, VALUE pass)
     /* First check DER */
     if (OSSL_DECODER_from_bio(dctx, bio) == 1)
         goto out;
+    OSSL_BIO_reset(bio);
 
     /* Then check PEM; multiple OSSL_DECODER_from_bio() calls may be needed */
-    OSSL_BIO_reset(bio);
     if (OSSL_DECODER_CTX_set_input_type(dctx, "PEM") != 1)
         goto out;
-    while (OSSL_DECODER_from_bio(dctx, bio) != 1) {
-        if (BIO_eof(bio))
+    /*
+     * First check for private key formats. This is to keep compatibility with
+     * ruby/openssl < 3.0 which decoded the following as a private key.
+     *
+     *     $ openssl ecparam -name prime256v1 -genkey -outform PEM
+     *     -----BEGIN EC PARAMETERS-----
+     *     BggqhkjOPQMBBw==
+     *     -----END EC PARAMETERS-----
+     *     -----BEGIN EC PRIVATE KEY-----
+     *     MHcCAQEEIAG8ugBbA5MHkqnZ9ujQF93OyUfL9tk8sxqM5Wv5tKg5oAoGCCqGSM49
+     *     AwEHoUQDQgAEVcjhJfkwqh5C7kGuhAf8XaAjVuG5ADwb5ayg/cJijCgs+GcXeedj
+     *     86avKpGH84DXUlB23C/kPt+6fXYlitUmXQ==
+     *     -----END EC PRIVATE KEY-----
+     *
+     * While the first PEM block is a proper encoding of ECParameters, thus
+     * OSSL_DECODER_from_bio() would pick it up, ruby/openssl used to return
+     * the latter instead. Existing applications expect this behavior.
+     *
+     * Note that normally, the input is supposed to contain a single decodable
+     * PEM block only, so this special handling should not create a new problem.
+     */
+    OSSL_DECODER_CTX_set_selection(dctx, EVP_PKEY_KEYPAIR);
+    while (1) {
+        if (OSSL_DECODER_from_bio(dctx, bio) == 1)
             goto out;
+        if (BIO_eof(bio))
+            break;
         pos2 = BIO_tell(bio);
         if (pos2 < 0 || pos2 <= pos)
+            break;
+        ossl_clear_error();
+        pos = pos2;
+    }
+
+    OSSL_BIO_reset(bio);
+    OSSL_DECODER_CTX_set_selection(dctx, 0);
+    while (1) {
+        if (OSSL_DECODER_from_bio(dctx, bio) == 1)
             goto out;
+        if (BIO_eof(bio))
+            break;
+        pos2 = BIO_tell(bio);
+        if (pos2 < 0 || pos2 <= pos)
+            break;
+        ossl_clear_error();
         pos = pos2;
     }
 
@@ -200,6 +239,7 @@ static VALUE
 pkey_ctx_apply_options0(VALUE args_v)
 {
     VALUE *args = (VALUE *)args_v;
+    Check_Type(args[1], T_HASH);
 
     rb_block_call(args[1], rb_intern("each"), 0, NULL,
                   pkey_ctx_apply_options_i, args[0]);
diff --git a/ext/openssl/ossl_pkey_ec.c b/ext/openssl/ossl_pkey_ec.c
index dee2154..06d59c2 100644
--- a/ext/openssl/ossl_pkey_ec.c
+++ b/ext/openssl/ossl_pkey_ec.c
@@ -414,6 +414,8 @@ ossl_ec_key_export(int argc, VALUE *argv, VALUE self)
     EC_KEY *ec;
 
     GetEC(self, ec);
+    if (EC_KEY_get0_public_key(ec) == NULL)
+        ossl_raise(eECError, "can't export - no public key set");
     if (EC_KEY_get0_private_key(ec))
         return ossl_pkey_export_traditional(argc, argv, self, 0);
     else
@@ -432,6 +434,8 @@ ossl_ec_key_to_der(VALUE self)
     EC_KEY *ec;
 
     GetEC(self, ec);
+    if (EC_KEY_get0_public_key(ec) == NULL)
+        ossl_raise(eECError, "can't export - no public key set");
     if (EC_KEY_get0_private_key(ec))
         return ossl_pkey_export_traditional(0, NULL, self, 1);
     else
diff --git a/ext/openssl/ossl_x509cert.c b/ext/openssl/ossl_x509cert.c
index 996f184..9443541 100644
--- a/ext/openssl/ossl_x509cert.c
+++ b/ext/openssl/ossl_x509cert.c
@@ -642,12 +642,12 @@ ossl_x509_set_extensions(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
     }
     GetX509(self, x509);
-    while ((ext = X509_delete_ext(x509, 0)))
-	X509_EXTENSION_free(ext);
+    for (i = X509_get_ext_count(x509); i > 0; i--)
+        X509_EXTENSION_free(X509_delete_ext(x509, 0));
     for (i=0; i<RARRAY_LEN(ary); i++) {
 	ext = GetX509ExtPtr(RARRAY_AREF(ary, i));
 	if (!X509_add_ext(x509, ext, -1)) { /* DUPs ext */
-	    ossl_raise(eX509CertError, NULL);
+	    ossl_raise(eX509CertError, "X509_add_ext");
 	}
     }
 
diff --git a/ext/openssl/ossl_x509crl.c b/ext/openssl/ossl_x509crl.c
index 863f028..6c1d915 100644
--- a/ext/openssl/ossl_x509crl.c
+++ b/ext/openssl/ossl_x509crl.c
@@ -474,12 +474,12 @@ ossl_x509crl_set_extensions(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
     }
     GetX509CRL(self, crl);
-    while ((ext = X509_CRL_delete_ext(crl, 0)))
-	X509_EXTENSION_free(ext);
+    for (i = X509_CRL_get_ext_count(crl); i > 0; i--)
+        X509_EXTENSION_free(X509_CRL_delete_ext(crl, 0));
     for (i=0; i<RARRAY_LEN(ary); i++) {
 	ext = GetX509ExtPtr(RARRAY_AREF(ary, i)); /* NO NEED TO DUP */
 	if (!X509_CRL_add_ext(crl, ext, -1)) {
-	    ossl_raise(eX509CRLError, NULL);
+	    ossl_raise(eX509CRLError, "X509_CRL_add_ext");
 	}
     }
 
diff --git a/ext/openssl/ossl_x509req.c b/ext/openssl/ossl_x509req.c
index 6eb91e9..77a7d3f 100644
--- a/ext/openssl/ossl_x509req.c
+++ b/ext/openssl/ossl_x509req.c
@@ -380,13 +380,13 @@ ossl_x509req_set_attributes(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Attr);
     }
     GetX509Req(self, req);
-    while ((attr = X509_REQ_delete_attr(req, 0)))
-	X509_ATTRIBUTE_free(attr);
+    for (i = X509_REQ_get_attr_count(req); i > 0; i--)
+        X509_ATTRIBUTE_free(X509_REQ_delete_attr(req, 0));
     for (i=0;i<RARRAY_LEN(ary); i++) {
 	item = RARRAY_AREF(ary, i);
 	attr = GetX509AttrPtr(item);
 	if (!X509_REQ_add1_attr(req, attr)) {
-	    ossl_raise(eX509ReqError, NULL);
+	    ossl_raise(eX509ReqError, "X509_REQ_add1_attr");
 	}
     }
     return ary;
diff --git a/ext/openssl/ossl_x509revoked.c b/ext/openssl/ossl_x509revoked.c
index 5fe6853..10b8aa4 100644
--- a/ext/openssl/ossl_x509revoked.c
+++ b/ext/openssl/ossl_x509revoked.c
@@ -223,13 +223,13 @@ ossl_x509revoked_set_extensions(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
     }
     GetX509Rev(self, rev);
-    while ((ext = X509_REVOKED_delete_ext(rev, 0)))
-	X509_EXTENSION_free(ext);
+    for (i = X509_REVOKED_get_ext_count(rev); i > 0; i--)
+        X509_EXTENSION_free(X509_REVOKED_delete_ext(rev, 0));
     for (i=0; i<RARRAY_LEN(ary); i++) {
 	item = RARRAY_AREF(ary, i);
 	ext = GetX509ExtPtr(item);
 	if(!X509_REVOKED_add_ext(rev, ext, -1)) {
-	    ossl_raise(eX509RevError, NULL);
+	    ossl_raise(eX509RevError, "X509_REVOKED_add_ext");
 	}
     }
 
diff --git a/test/openssl/test_hmac.rb b/test/openssl/test_hmac.rb
index 47cb371..08b888d 100644
--- a/test/openssl/test_hmac.rb
+++ b/test/openssl/test_hmac.rb
@@ -63,6 +63,14 @@ class OpenSSL::TestHMAC < OpenSSL::TestCase
     b64digest = OpenSSL::HMAC.base64digest("MD5", key, "Hi There")
     assert_equal "kpRyejY4uxwT9I74FYv8nQ==", b64digest
   end
+
+  def test_zero_length_key
+    # Empty string as the key
+    hexdigest = OpenSSL::HMAC.hexdigest("SHA256", "\0"*32, "test")
+    assert_equal "43b0cef99265f9e34c10ea9d3501926d27b39f57c6d674561d8ba236e7a819fb", hexdigest
+    hexdigest = OpenSSL::HMAC.hexdigest("SHA256", "", "test")
+    assert_equal "43b0cef99265f9e34c10ea9d3501926d27b39f57c6d674561d8ba236e7a819fb", hexdigest
+  end
 end
 
 end
diff --git a/test/openssl/test_pkey_dsa.rb b/test/openssl/test_pkey_dsa.rb
index 726b7db..de6aa63 100644
--- a/test/openssl/test_pkey_dsa.rb
+++ b/test/openssl/test_pkey_dsa.rb
@@ -28,6 +28,25 @@ class OpenSSL::TestPKeyDSA < OpenSSL::PKeyTestCase
     end
   end
 
+  def test_generate
+    # DSA.generate used to call DSA_generate_parameters_ex(), which adjusts the
+    # size of q according to the size of p
+    key1024 = OpenSSL::PKey::DSA.generate(1024)
+    assert_predicate key1024, :private?
+    assert_equal 1024, key1024.p.num_bits
+    assert_equal 160, key1024.q.num_bits
+
+    key2048 = OpenSSL::PKey::DSA.generate(2048)
+    assert_equal 2048, key2048.p.num_bits
+    assert_equal 256, key2048.q.num_bits
+
+    if ENV["OSSL_TEST_ALL"] == "1" # slow
+      key3072 = OpenSSL::PKey::DSA.generate(3072)
+      assert_equal 3072, key3072.p.num_bits
+      assert_equal 256, key3072.q.num_bits
+    end
+  end
+
   def test_sign_verify
     dsa512 = Fixtures.pkey("dsa512")
     data = "Sign me!"
diff --git a/test/openssl/test_pkey_ec.rb b/test/openssl/test_pkey_ec.rb
index ffe5a94..9a4818d 100644
--- a/test/openssl/test_pkey_ec.rb
+++ b/test/openssl/test_pkey_ec.rb
@@ -61,8 +61,10 @@ class OpenSSL::TestEC < OpenSSL::PKeyTestCase
   def test_generate_key
     ec = OpenSSL::PKey::EC.new("prime256v1")
     assert_equal false, ec.private?
+    assert_raise(OpenSSL::PKey::ECError) { ec.to_der }
     ec.generate_key!
     assert_equal true, ec.private?
+    assert_nothing_raised { ec.to_der }
   end if !openssl?(3, 0, 0)
 
   def test_marshal
@@ -199,6 +201,29 @@ class OpenSSL::TestEC < OpenSSL::PKeyTestCase
     assert_equal pem, p256.export
   end
 
+  def test_ECPrivateKey_with_parameters
+    p256 = Fixtures.pkey("p256")
+
+    # The format used by "openssl ecparam -name prime256v1 -genkey -outform PEM"
+    #
+    # "EC PARAMETERS" block should be ignored if it is followed by an
+    # "EC PRIVATE KEY" block
+    in_pem = <<~EOF
+    -----BEGIN EC PARAMETERS-----
+    BggqhkjOPQMBBw==
+    -----END EC PARAMETERS-----
+    -----BEGIN EC PRIVATE KEY-----
+    MHcCAQEEIID49FDqcf1O1eO8saTgG70UbXQw9Fqwseliit2aWhH1oAoGCCqGSM49
+    AwEHoUQDQgAEFglk2c+oVUIKQ64eZG9bhLNPWB7lSZ/ArK41eGy5wAzU/0G51Xtt
+    CeBUl+MahZtn9fO1JKdF4qJmS39dXnpENg==
+    -----END EC PRIVATE KEY-----
+    EOF
+
+    key = OpenSSL::PKey::EC.new(in_pem)
+    assert_same_ec p256, key
+    assert_equal p256.to_der, key.to_der
+  end
+
   def test_ECPrivateKey_encrypted
     p256 = Fixtures.pkey("p256")
     # key = abcdef
diff --git a/test/openssl/test_pkey_rsa.rb b/test/openssl/test_pkey_rsa.rb
index 4bb39ed..fa84b76 100644
--- a/test/openssl/test_pkey_rsa.rb
+++ b/test/openssl/test_pkey_rsa.rb
@@ -108,6 +108,11 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
                                       salt_length: 20, mgf1_hash: "SHA1")
     # Defaults to PKCS #1 v1.5 padding => verification failure
     assert_equal false, key.verify("SHA256", sig_pss, data)
+
+    # option type check
+    assert_raise_with_message(TypeError, /expected Hash/) {
+      key.sign("SHA256", data, ["x"])
+    }
   end
 
   def test_sign_verify_raw
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index a7607da..39964bf 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -676,10 +676,16 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     #     buzz.example.net, respectively).  ...
     assert_equal(true, OpenSSL::SSL.verify_certificate_identity(
       create_cert_with_san('DNS:baz*.example.com'), 'baz1.example.com'))
+
+    # LibreSSL 3.5.0+ doesn't support other wildcard certificates
+    # (it isn't required to, as RFC states MAY, not MUST)
+    return if libressl?(3, 5, 0)
+
     assert_equal(true, OpenSSL::SSL.verify_certificate_identity(
       create_cert_with_san('DNS:*baz.example.com'), 'foobaz.example.com'))
     assert_equal(true, OpenSSL::SSL.verify_certificate_identity(
       create_cert_with_san('DNS:b*z.example.com'), 'buzz.example.com'))
+
     # Section 6.4.3 of RFC6125 states that client should NOT match identifier
     # where wildcard is other than left-most label.
     #

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