From cd38f6c5e141f18de1001b36baf3f18162d3d333 Mon Sep 17 00:00:00 2001
From: Kazuki Yamaguchi <k@rhe.jp>
Date: Thu, 14 May 2026 00:47:15 +0900
Subject: Merge openssl-4.0.2

The changes can be found at:

    https://github.com/ruby/openssl/compare/v4.0.1...v4.0.2
---
 ext/openssl/History.md             | 22 ++++++++++++
 ext/openssl/extconf.rb             |  3 ++
 ext/openssl/lib/openssl/version.rb |  2 +-
 ext/openssl/openssl.gemspec        |  2 +-
 ext/openssl/openssl_missing.h      | 23 ++++++++++++
 ext/openssl/ossl.c                 | 22 +++++++++---
 ext/openssl/ossl_asn1.c            | 47 +++++++++++++-----------
 ext/openssl/ossl_bio.c             |  6 +++-
 ext/openssl/ossl_ocsp.c            |  5 ++-
 ext/openssl/ossl_pkey.h            |  1 -
 ext/openssl/ossl_ts.c              |  2 +-
 ext/openssl/ossl_x509.h            | 12 +++----
 ext/openssl/ossl_x509attr.c        |  9 ++---
 ext/openssl/ossl_x509cert.c        | 12 +++----
 ext/openssl/ossl_x509crl.c         | 10 +++---
 ext/openssl/ossl_x509ext.c         | 19 +++++++---
 ext/openssl/ossl_x509name.c        |  5 +--
 ext/openssl/ossl_x509req.c         |  4 +--
 ext/openssl/ossl_x509revoked.c     |  7 ++--
 ext/openssl/ossl_x509store.c       | 10 +++---
 test/openssl/test_ossl.rb          | 10 ++++++
 test/openssl/test_pkey_rsa.rb      | 74 +++++++++++++++++++-------------------
 test/openssl/test_ssl.rb           |  8 +++--
 23 files changed, 203 insertions(+), 112 deletions(-)

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index c78c7e4633..ce01b3e0f2 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,3 +1,9 @@
+Version 4.0.2
+=============
+
+Merged changes in 3.2.4 and 3.3.3.
+
+
 Version 4.0.1
 =============
 
@@ -103,6 +109,12 @@ Notable changes
   [[GitHub #983]](https://github.com/ruby/openssl/pull/983)
 
 
+Version 3.3.3
+=============
+
+Merged changes in 3.2.4.
+
+
 Version 3.3.2
 =============
 
@@ -191,6 +203,16 @@ And various non-user-visible changes and bug fixes. Please see the commit
 history for more details.
 
 
+Version 3.2.4
+=============
+
+Notable changes
+---------------
+
+* Add support for OpenSSL 4.0.
+  [[GitHub #1051]](https://github.com/ruby/openssl/pull/1051)
+
+
 Version 3.2.3
 =============
 
diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index a897c86b65..06ed4f6ac3 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -169,6 +169,9 @@ have_func("TS_VERIFY_CTX_set0_certs(NULL, NULL)", ts_h)
 # added in 3.5.0
 have_func("SSL_get0_peer_signature_name(NULL, NULL)", ssl_h)
 
+# added in 4.0.0
+have_func("ASN1_BIT_STRING_set1(NULL, NULL, 0, 0)", "openssl/asn1.h")
+
 Logging::message "=== Checking done. ===\n"
 
 # Append flags from environment variables.
diff --git a/ext/openssl/lib/openssl/version.rb b/ext/openssl/lib/openssl/version.rb
index 45c150be11..395a720a31 100644
--- a/ext/openssl/lib/openssl/version.rb
+++ b/ext/openssl/lib/openssl/version.rb
@@ -2,5 +2,5 @@
 
 module OpenSSL
   # The version string of Ruby/OpenSSL.
-  VERSION = "4.0.1"
+  VERSION = "4.0.2"
 end
diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
index c594c6f177..af1775e3b0 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       = "4.0.1"
+  spec.version       = "4.0.2"
   spec.authors       = ["Martin Bosslet", "SHIBATA Hiroshi", "Zachary Scott", "Kazuki Yamaguchi"]
   spec.email         = ["ruby-core@ruby-lang.org"]
   spec.summary       = %q{SSL/TLS and general-purpose cryptography for Ruby}
diff --git a/ext/openssl/openssl_missing.h b/ext/openssl/openssl_missing.h
index 6592f9ccea..ed3b5b7c0f 100644
--- a/ext/openssl/openssl_missing.h
+++ b/ext/openssl/openssl_missing.h
@@ -29,4 +29,27 @@
 #  define EVP_PKEY_eq(a, b) EVP_PKEY_cmp(a, b)
 #endif
 
+/* added in 4.0.0 */
+#ifndef HAVE_ASN1_BIT_STRING_SET1
+static inline int
+ASN1_BIT_STRING_set1(ASN1_BIT_STRING *bitstr, const uint8_t *data,
+                     size_t length, int unused_bits)
+{
+    if (length > INT_MAX || !ASN1_STRING_set(bitstr, data, (int)length))
+        return 0;
+    bitstr->flags &= ~(ASN1_STRING_FLAG_BITS_LEFT | 0x07);
+    bitstr->flags |= ASN1_STRING_FLAG_BITS_LEFT | unused_bits;
+    return 1;
+}
+
+static inline int
+ASN1_BIT_STRING_get_length(const ASN1_BIT_STRING *bitstr, size_t *length,
+                           int *unused_bits)
+{
+    *length = bitstr->length;
+    *unused_bits = bitstr->flags & 0x07;
+    return 1;
+}
+#endif
+
 #endif /* _OSSL_OPENSSL_MISSING_H_ */
diff --git a/ext/openssl/ossl.c b/ext/openssl/ossl.c
index 98127fcba0..5716e6f100 100644
--- a/ext/openssl/ossl.c
+++ b/ext/openssl/ossl.c
@@ -34,7 +34,11 @@ ossl_##name##_ary2sk0(VALUE ary)                                \
                        " of class ##type##");                   \
         }                                                       \
         x = dup(val); /* NEED TO DUP */                         \
-        sk_##type##_push(sk, x);                                \
+        if (!sk_##type##_push(sk, x)) {                         \
+            type##_free(x);                                     \
+            sk_##type##_pop_free(sk, type##_free);              \
+            ossl_raise(eOSSLError, NULL);                       \
+        }                                                       \
     }                                                           \
     return (VALUE)sk;                                           \
 }                                                               \
@@ -523,10 +527,18 @@ ossl_fips_mode_set(VALUE self, VALUE enabled)
 static VALUE
 ossl_crypto_fixed_length_secure_compare(VALUE dummy, VALUE str1, VALUE str2)
 {
-    const unsigned char *p1 = (const unsigned char *)StringValuePtr(str1);
-    const unsigned char *p2 = (const unsigned char *)StringValuePtr(str2);
-    long len1 = RSTRING_LEN(str1);
-    long len2 = RSTRING_LEN(str2);
+    const unsigned char *p1;
+    const unsigned char *p2;
+    long len1;
+    long len2;
+
+    StringValue(str1);
+    StringValue(str2);
+
+    p1 = (const unsigned char *)RSTRING_PTR(str1);
+    p2 = (const unsigned char *)RSTRING_PTR(str2);
+    len1 = RSTRING_LEN(str1);
+    len2 = RSTRING_LEN(str2);
 
     if (len1 != len2) {
         ossl_raise(rb_eArgError, "inputs must be of equal length");
diff --git a/ext/openssl/ossl_asn1.c b/ext/openssl/ossl_asn1.c
index 71a87f0463..67c03b7f98 100644
--- a/ext/openssl/ossl_asn1.c
+++ b/ext/openssl/ossl_asn1.c
@@ -130,15 +130,17 @@ asn1integer_to_num(const ASN1_INTEGER *ai)
     if (!ai) {
         ossl_raise(rb_eTypeError, "ASN1_INTEGER is NULL!");
     }
+
+    num = ossl_bn_new(BN_value_one());
+    bn = GetBNPtr(num);
+
     if (ASN1_STRING_type(ai) == V_ASN1_ENUMERATED)
-        bn = ASN1_ENUMERATED_to_BN(ai, NULL);
+        bn = ASN1_ENUMERATED_to_BN(ai, bn);
     else
-        bn = ASN1_INTEGER_to_BN(ai, NULL);
+        bn = ASN1_INTEGER_to_BN(ai, bn);
 
     if (!bn)
         ossl_raise(eOSSLError, NULL);
-    num = ossl_bn_new(bn);
-    BN_free(bn);
 
     return num;
 }
@@ -226,7 +228,7 @@ obj_to_asn1int(VALUE obj)
 }
 
 static ASN1_BIT_STRING*
-obj_to_asn1bstr(VALUE obj, long unused_bits)
+obj_to_asn1bstr(VALUE obj, int unused_bits)
 {
     ASN1_BIT_STRING *bstr;
 
@@ -234,11 +236,11 @@ obj_to_asn1bstr(VALUE obj, long unused_bits)
         ossl_raise(eASN1Error, "unused_bits for a bitstring value must be in "\
                    "the range 0 to 7");
     StringValue(obj);
-    if(!(bstr = ASN1_BIT_STRING_new()))
-        ossl_raise(eASN1Error, NULL);
-    ASN1_BIT_STRING_set(bstr, (unsigned char *)RSTRING_PTR(obj), RSTRING_LENINT(obj));
-    bstr->flags &= ~(ASN1_STRING_FLAG_BITS_LEFT|0x07); /* clear */
-    bstr->flags |= ASN1_STRING_FLAG_BITS_LEFT | unused_bits;
+    if (!(bstr = ASN1_BIT_STRING_new()))
+        ossl_raise(eASN1Error, "ASN1_BIT_STRING_new");
+    if (!ASN1_BIT_STRING_set1(bstr, (uint8_t *)RSTRING_PTR(obj),
+                              RSTRING_LEN(obj), unused_bits))
+        ossl_raise(eASN1Error, "ASN1_BIT_STRING_set1");
 
     return bstr;
 }
@@ -362,22 +364,25 @@ decode_int(unsigned char* der, long length)
 }
 
 static VALUE
-decode_bstr(unsigned char* der, long length, long *unused_bits)
+decode_bstr(unsigned char* der, long length, int *unused_bits)
 {
     ASN1_BIT_STRING *bstr;
     const unsigned char *p;
-    long len;
+    size_t len;
     VALUE ret;
+    int state;
 
     p = der;
-    if(!(bstr = d2i_ASN1_BIT_STRING(NULL, &p, length)))
-        ossl_raise(eASN1Error, NULL);
-    len = bstr->length;
-    *unused_bits = 0;
-    if(bstr->flags & ASN1_STRING_FLAG_BITS_LEFT)
-        *unused_bits = bstr->flags & 0x07;
-    ret = rb_str_new((const char *)bstr->data, len);
+    if (!(bstr = d2i_ASN1_BIT_STRING(NULL, &p, length)))
+        ossl_raise(eASN1Error, "d2i_ASN1_BIT_STRING");
+    if (!ASN1_BIT_STRING_get_length(bstr, &len, unused_bits)) {
+        ASN1_BIT_STRING_free(bstr);
+        ossl_raise(eASN1Error, "ASN1_BIT_STRING_get_length");
+    }
+    ret = ossl_str_new((const char *)ASN1_STRING_get0_data(bstr), len, &state);
     ASN1_BIT_STRING_free(bstr);
+    if (state)
+        rb_jump_tag(state);
 
     return ret;
 }
@@ -761,7 +766,7 @@ int_ossl_asn1_decode0_prim(unsigned char **pp, long length, long hlen, int tag,
 {
     VALUE value, asn1data;
     unsigned char *p;
-    long flag = 0;
+    int flag = 0;
 
     p = *pp;
 
@@ -818,7 +823,7 @@ int_ossl_asn1_decode0_prim(unsigned char **pp, long length, long hlen, int tag,
         asn1data = rb_obj_alloc(klass);
         ossl_asn1_initialize(4, args, asn1data);
         if(tag == V_ASN1_BIT_STRING){
-            rb_ivar_set(asn1data, sivUNUSED_BITS, LONG2NUM(flag));
+            rb_ivar_set(asn1data, sivUNUSED_BITS, INT2NUM(flag));
         }
     }
     else {
diff --git a/ext/openssl/ossl_bio.c b/ext/openssl/ossl_bio.c
index 4edde5091d..cc03c5d5f7 100644
--- a/ext/openssl/ossl_bio.c
+++ b/ext/openssl/ossl_bio.c
@@ -32,7 +32,11 @@ ossl_membio2str(BIO *bio)
     int state;
     BUF_MEM *buf;
 
-    BIO_get_mem_ptr(bio, &buf);
+    if (BIO_get_mem_ptr(bio, &buf) <= 0) {
+        BIO_free(bio);
+        ossl_raise(eOSSLError, "BIO_get_mem_ptr");
+    }
+
     ret = ossl_str_new(buf->data, buf->length, &state);
     BIO_free(bio);
     if (state)
diff --git a/ext/openssl/ossl_ocsp.c b/ext/openssl/ossl_ocsp.c
index ddb67fcf07..9dd4b466d2 100644
--- a/ext/openssl/ossl_ocsp.c
+++ b/ext/openssl/ossl_ocsp.c
@@ -922,7 +922,7 @@ ossl_ocspbres_get_status(VALUE self)
         VALUE ext = rb_ary_new();
         int ext_count = OCSP_SINGLERESP_get_ext_count(single);
         for (int j = 0; j < ext_count; j++) {
-            X509_EXTENSION *x509ext = OCSP_SINGLERESP_get_ext(single, j);
+            const X509_EXTENSION *x509ext = OCSP_SINGLERESP_get_ext(single, j);
             rb_ary_push(ext, ossl_x509ext_new(x509ext));
         }
         rb_ary_push(ary, ext);
@@ -1341,7 +1341,6 @@ static VALUE
 ossl_ocspsres_get_extensions(VALUE self)
 {
     OCSP_SINGLERESP *sres;
-    X509_EXTENSION *ext;
     int count, i;
     VALUE ary;
 
@@ -1350,7 +1349,7 @@ ossl_ocspsres_get_extensions(VALUE self)
     count = OCSP_SINGLERESP_get_ext_count(sres);
     ary = rb_ary_new2(count);
     for (i = 0; i < count; i++) {
-        ext = OCSP_SINGLERESP_get_ext(sres, i);
+        const X509_EXTENSION *ext = OCSP_SINGLERESP_get_ext(sres, i);
         rb_ary_push(ary, ossl_x509ext_new(ext)); /* will dup */
     }
 
diff --git a/ext/openssl/ossl_pkey.h b/ext/openssl/ossl_pkey.h
index 023361b90f..efba33b752 100644
--- a/ext/openssl/ossl_pkey.h
+++ b/ext/openssl/ossl_pkey.h
@@ -71,7 +71,6 @@ void Init_ossl_dh(void);
  * EC
  */
 extern VALUE cEC;
-VALUE ossl_ec_new(EVP_PKEY *);
 void Init_ossl_ec(void);
 
 #define OSSL_PKEY_BN_DEF_GETTER0(_keytype, _type, _name, _get)          \
diff --git a/ext/openssl/ossl_ts.c b/ext/openssl/ossl_ts.c
index b31a854a63..393e08acff 100644
--- a/ext/openssl/ossl_ts.c
+++ b/ext/openssl/ossl_ts.c
@@ -706,7 +706,7 @@ ossl_ts_resp_get_tsa_certificate(VALUE self)
     TS_RESP *resp;
     PKCS7 *p7;
     PKCS7_SIGNER_INFO *ts_info;
-    X509 *cert;
+    const X509 *cert;
 
     GetTSResponse(self, resp);
     if (!(p7 = TS_RESP_get_token(resp)))
diff --git a/ext/openssl/ossl_x509.h b/ext/openssl/ossl_x509.h
index d25167ee7b..71932ef1a9 100644
--- a/ext/openssl/ossl_x509.h
+++ b/ext/openssl/ossl_x509.h
@@ -29,7 +29,7 @@ void Init_ossl_x509(void);
  */
 extern VALUE cX509Attr;
 
-VALUE ossl_x509attr_new(X509_ATTRIBUTE *);
+VALUE ossl_x509attr_new(const X509_ATTRIBUTE *);
 X509_ATTRIBUTE *GetX509AttrPtr(VALUE);
 void Init_ossl_x509attr(void);
 
@@ -38,7 +38,7 @@ void Init_ossl_x509attr(void);
  */
 extern VALUE cX509Cert;
 
-VALUE ossl_x509_new(X509 *);
+VALUE ossl_x509_new(const X509 *);
 X509 *GetX509CertPtr(VALUE);
 X509 *DupX509CertPtr(VALUE);
 void Init_ossl_x509cert(void);
@@ -46,7 +46,7 @@ void Init_ossl_x509cert(void);
 /*
  * X509CRL
  */
-VALUE ossl_x509crl_new(X509_CRL *);
+VALUE ossl_x509crl_new(const X509_CRL *);
 X509_CRL *GetX509CRLPtr(VALUE);
 void Init_ossl_x509crl(void);
 
@@ -55,14 +55,14 @@ void Init_ossl_x509crl(void);
  */
 extern VALUE cX509Ext;
 
-VALUE ossl_x509ext_new(X509_EXTENSION *);
+VALUE ossl_x509ext_new(const X509_EXTENSION *);
 X509_EXTENSION *GetX509ExtPtr(VALUE);
 void Init_ossl_x509ext(void);
 
 /*
  * X509Name
  */
-VALUE ossl_x509name_new(X509_NAME *);
+VALUE ossl_x509name_new(const X509_NAME *);
 X509_NAME *GetX509NamePtr(VALUE);
 void Init_ossl_x509name(void);
 
@@ -77,7 +77,7 @@ void Init_ossl_x509req(void);
  */
 extern VALUE cX509Rev;
 
-VALUE ossl_x509revoked_new(X509_REVOKED *);
+VALUE ossl_x509revoked_new(const X509_REVOKED *);
 X509_REVOKED *DupX509RevokedPtr(VALUE);
 void Init_ossl_x509revoked(void);
 
diff --git a/ext/openssl/ossl_x509attr.c b/ext/openssl/ossl_x509attr.c
index 4769e56e1e..b0773e7a7d 100644
--- a/ext/openssl/ossl_x509attr.c
+++ b/ext/openssl/ossl_x509attr.c
@@ -48,13 +48,14 @@ static const rb_data_type_t ossl_x509attr_type = {
  * Public
  */
 VALUE
-ossl_x509attr_new(X509_ATTRIBUTE *attr)
+ossl_x509attr_new(const X509_ATTRIBUTE *attr)
 {
     X509_ATTRIBUTE *new;
     VALUE obj;
 
     obj = NewX509Attr(cX509Attr);
-    new = X509_ATTRIBUTE_dup(attr);
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    new = X509_ATTRIBUTE_dup((X509_ATTRIBUTE *)attr);
     if (!new)
         ossl_raise(eX509AttrError, "X509_ATTRIBUTE_dup");
     SetX509Attr(obj, new);
@@ -196,7 +197,7 @@ ossl_x509attr_set_value(VALUE self, VALUE value)
         ossl_raise(eX509AttrError, "attribute value must be ASN1::Set");
 
     if (X509_ATTRIBUTE_count(attr)) { /* populated, reset first */
-        ASN1_OBJECT *obj = X509_ATTRIBUTE_get0_object(attr);
+        const ASN1_OBJECT *obj = X509_ATTRIBUTE_get0_object(attr);
         X509_ATTRIBUTE *new_attr = X509_ATTRIBUTE_create_by_OBJ(NULL, obj, 0, NULL, -1);
         if (!new_attr) {
             sk_ASN1_TYPE_pop_free(sk, ASN1_TYPE_free);
@@ -240,7 +241,7 @@ ossl_x509attr_get_value(VALUE self)
 
     count = X509_ATTRIBUTE_count(attr);
     for (i = 0; i < count; i++)
-        sk_ASN1_TYPE_push(sk, X509_ATTRIBUTE_get0_type(attr, i));
+        sk_ASN1_TYPE_push(sk, (ASN1_TYPE *)X509_ATTRIBUTE_get0_type(attr, i));
 
     if ((len = i2d_ASN1_SET_ANY(sk, NULL)) <= 0) {
         sk_ASN1_TYPE_free(sk);
diff --git a/ext/openssl/ossl_x509cert.c b/ext/openssl/ossl_x509cert.c
index 95679c7d24..de246759ab 100644
--- a/ext/openssl/ossl_x509cert.c
+++ b/ext/openssl/ossl_x509cert.c
@@ -48,13 +48,14 @@ static const rb_data_type_t ossl_x509_type = {
  * Public
  */
 VALUE
-ossl_x509_new(X509 *x509)
+ossl_x509_new(const X509 *x509)
 {
     X509 *new;
     VALUE obj;
 
     obj = NewX509(cX509Cert);
-    new = X509_dup(x509);
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    new = X509_dup((X509 *)x509);
     if (!new)
         ossl_raise(eX509CertError, "X509_dup");
     SetX509(obj, new);
@@ -345,7 +346,7 @@ static VALUE
 ossl_x509_get_subject(VALUE self)
 {
     X509 *x509;
-    X509_NAME *name;
+    const X509_NAME *name;
 
     GetX509(self, x509);
     if (!(name = X509_get_subject_name(x509))) { /* NO DUP - don't free! */
@@ -380,7 +381,7 @@ static VALUE
 ossl_x509_get_issuer(VALUE self)
 {
     X509 *x509;
-    X509_NAME *name;
+    const X509_NAME *name;
 
     GetX509(self, x509);
     if(!(name = X509_get_issuer_name(x509))) { /* NO DUP - don't free! */
@@ -603,14 +604,13 @@ ossl_x509_get_extensions(VALUE self)
 {
     X509 *x509;
     int count, i;
-    X509_EXTENSION *ext;
     VALUE ary;
 
     GetX509(self, x509);
     count = X509_get_ext_count(x509);
     ary = rb_ary_new_capa(count);
     for (i=0; i<count; i++) {
-        ext = X509_get_ext(x509, i); /* NO DUP - don't free! */
+        const X509_EXTENSION *ext = X509_get_ext(x509, i);
         rb_ary_push(ary, ossl_x509ext_new(ext));
     }
 
diff --git a/ext/openssl/ossl_x509crl.c b/ext/openssl/ossl_x509crl.c
index a221429c34..9b59bda9e2 100644
--- a/ext/openssl/ossl_x509crl.c
+++ b/ext/openssl/ossl_x509crl.c
@@ -58,13 +58,14 @@ GetX509CRLPtr(VALUE obj)
 }
 
 VALUE
-ossl_x509crl_new(X509_CRL *crl)
+ossl_x509crl_new(const X509_CRL *crl)
 {
     X509_CRL *tmp;
     VALUE obj;
 
     obj = NewX509CRL(cX509CRL);
-    tmp = X509_CRL_dup(crl);
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    tmp = X509_CRL_dup((X509_CRL *)crl);
     if (!tmp)
         ossl_raise(eX509CRLError, "X509_CRL_dup");
     SetX509CRL(obj, tmp);
@@ -289,7 +290,7 @@ ossl_x509crl_get_revoked(VALUE self)
     num = sk_X509_REVOKED_num(sk);
     ary = rb_ary_new_capa(num);
     for(i=0; i<num; i++) {
-        X509_REVOKED *rev = sk_X509_REVOKED_value(sk, i);
+        const X509_REVOKED *rev = sk_X509_REVOKED_value(sk, i);
         rb_ary_push(ary, ossl_x509revoked_new(rev));
     }
 
@@ -443,14 +444,13 @@ ossl_x509crl_get_extensions(VALUE self)
 {
     X509_CRL *crl;
     int count, i;
-    X509_EXTENSION *ext;
     VALUE ary;
 
     GetX509CRL(self, crl);
     count = X509_CRL_get_ext_count(crl);
     ary = rb_ary_new_capa(count);
     for (i=0; i<count; i++) {
-        ext = X509_CRL_get_ext(crl, i); /* NO DUP - don't free! */
+        const X509_EXTENSION *ext = X509_CRL_get_ext(crl, i);
         rb_ary_push(ary, ossl_x509ext_new(ext));
     }
 
diff --git a/ext/openssl/ossl_x509ext.c b/ext/openssl/ossl_x509ext.c
index ef66ecc3fe..1fe727d3f1 100644
--- a/ext/openssl/ossl_x509ext.c
+++ b/ext/openssl/ossl_x509ext.c
@@ -62,13 +62,14 @@ static const rb_data_type_t ossl_x509ext_type = {
  * Public
  */
 VALUE
-ossl_x509ext_new(X509_EXTENSION *ext)
+ossl_x509ext_new(const X509_EXTENSION *ext)
 {
     X509_EXTENSION *new;
     VALUE obj;
 
     obj = NewX509Ext(cX509Ext);
-    new = X509_EXTENSION_dup(ext);
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    new = X509_EXTENSION_dup((X509_EXTENSION *)ext);
     if (!new)
         ossl_raise(eX509ExtError, "X509_EXTENSION_dup");
     SetX509Ext(obj, new);
@@ -338,12 +339,20 @@ ossl_x509ext_set_value(VALUE self, VALUE data)
     GetX509Ext(self, ext);
     data = ossl_to_der_if_possible(data);
     StringValue(data);
-    asn1s = X509_EXTENSION_get_data(ext);
 
+    asn1s = ASN1_OCTET_STRING_new();
+    if (!asn1s)
+        ossl_raise(eX509ExtError, "ASN1_OCTET_STRING_new");
     if (!ASN1_OCTET_STRING_set(asn1s, (unsigned char *)RSTRING_PTR(data),
                                RSTRING_LENINT(data))) {
+        ASN1_OCTET_STRING_free(asn1s);
         ossl_raise(eX509ExtError, "ASN1_OCTET_STRING_set");
     }
+    if (!X509_EXTENSION_set_data(ext, asn1s)) {
+        ASN1_OCTET_STRING_free(asn1s);
+        ossl_raise(eX509ExtError, "X509_EXTENSION_set_data");
+    }
+    ASN1_OCTET_STRING_free(asn1s);
 
     return data;
 }
@@ -386,7 +395,7 @@ ossl_x509ext_get_value(VALUE obj)
     if (!(out = BIO_new(BIO_s_mem())))
         ossl_raise(eX509ExtError, NULL);
     if (!X509V3_EXT_print(out, ext, 0, 0))
-        ASN1_STRING_print(out, (ASN1_STRING *)X509_EXTENSION_get_data(ext));
+        ASN1_STRING_print(out, X509_EXTENSION_get_data(ext));
     ret = ossl_membio2str(out);
 
     return ret;
@@ -396,7 +405,7 @@ static VALUE
 ossl_x509ext_get_value_der(VALUE obj)
 {
     X509_EXTENSION *ext;
-    ASN1_OCTET_STRING *value;
+    const ASN1_OCTET_STRING *value;
 
     GetX509Ext(obj, ext);
     if ((value = X509_EXTENSION_get_data(ext)) == NULL)
diff --git a/ext/openssl/ossl_x509name.c b/ext/openssl/ossl_x509name.c
index 5b3c3f7261..2b66a4a097 100644
--- a/ext/openssl/ossl_x509name.c
+++ b/ext/openssl/ossl_x509name.c
@@ -53,13 +53,14 @@ static const rb_data_type_t ossl_x509name_type = {
  * Public
  */
 VALUE
-ossl_x509name_new(X509_NAME *name)
+ossl_x509name_new(const X509_NAME *name)
 {
     X509_NAME *new;
     VALUE obj;
 
     obj = NewX509Name(cX509Name);
-    new = X509_NAME_dup(name);
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    new = X509_NAME_dup((X509_NAME *)name);
     if (!new)
         ossl_raise(eX509NameError, "X509_NAME_dup");
     SetX509Name(obj, new);
diff --git a/ext/openssl/ossl_x509req.c b/ext/openssl/ossl_x509req.c
index 433cc461a9..ad5dd08033 100644
--- a/ext/openssl/ossl_x509req.c
+++ b/ext/openssl/ossl_x509req.c
@@ -231,7 +231,7 @@ static VALUE
 ossl_x509req_get_subject(VALUE self)
 {
     X509_REQ *req;
-    X509_NAME *name;
+    const X509_NAME *name;
 
     GetX509Req(self, req);
     if (!(name = X509_REQ_get_subject_name(req))) { /* NO DUP - don't free */
@@ -351,7 +351,7 @@ ossl_x509req_get_attributes(VALUE self)
 {
     X509_REQ *req;
     int count, i;
-    X509_ATTRIBUTE *attr;
+    const X509_ATTRIBUTE *attr;
     VALUE ary;
 
     GetX509Req(self, req);
diff --git a/ext/openssl/ossl_x509revoked.c b/ext/openssl/ossl_x509revoked.c
index b88c390c72..0151961e9f 100644
--- a/ext/openssl/ossl_x509revoked.c
+++ b/ext/openssl/ossl_x509revoked.c
@@ -48,13 +48,14 @@ static const rb_data_type_t ossl_x509rev_type = {
  * PUBLIC
  */
 VALUE
-ossl_x509revoked_new(X509_REVOKED *rev)
+ossl_x509revoked_new(const X509_REVOKED *rev)
 {
     X509_REVOKED *new;
     VALUE obj;
 
     obj = NewX509Rev(cX509Rev);
-    new = X509_REVOKED_dup(rev);
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    new = X509_REVOKED_dup((X509_REVOKED *)rev);
     if (!new)
         ossl_raise(eX509RevError, "X509_REVOKED_dup");
     SetX509Rev(obj, new);
@@ -185,7 +186,7 @@ ossl_x509revoked_get_extensions(VALUE self)
 {
     X509_REVOKED *rev;
     int count, i;
-    X509_EXTENSION *ext;
+    const X509_EXTENSION *ext;
     VALUE ary;
 
     GetX509Rev(self, rev);
diff --git a/ext/openssl/ossl_x509store.c b/ext/openssl/ossl_x509store.c
index be1458cec5..408e18c6c4 100644
--- a/ext/openssl/ossl_x509store.c
+++ b/ext/openssl/ossl_x509store.c
@@ -512,10 +512,8 @@ static void
 ossl_x509stctx_free(void *ptr)
 {
     X509_STORE_CTX *ctx = ptr;
-    if (X509_STORE_CTX_get0_untrusted(ctx))
-        sk_X509_pop_free(X509_STORE_CTX_get0_untrusted(ctx), X509_free);
-    if (X509_STORE_CTX_get0_cert(ctx))
-        X509_free(X509_STORE_CTX_get0_cert(ctx));
+    sk_X509_pop_free(X509_STORE_CTX_get0_untrusted(ctx), X509_free);
+    X509_free((X509 *)X509_STORE_CTX_get0_cert(ctx));
     X509_STORE_CTX_free(ctx);
 }
 
@@ -736,7 +734,7 @@ static VALUE
 ossl_x509stctx_get_curr_cert(VALUE self)
 {
     X509_STORE_CTX *ctx;
-    X509 *x509;
+    const X509 *x509;
 
     GetX509StCtx(self, ctx);
     x509 = X509_STORE_CTX_get_current_cert(ctx);
@@ -758,7 +756,7 @@ static VALUE
 ossl_x509stctx_get_curr_crl(VALUE self)
 {
     X509_STORE_CTX *ctx;
-    X509_CRL *crl;
+    const X509_CRL *crl;
 
     GetX509StCtx(self, ctx);
     crl = X509_STORE_CTX_get0_current_crl(ctx);
diff --git a/test/openssl/test_ossl.rb b/test/openssl/test_ossl.rb
index 51262985f5..1b9bde53ef 100644
--- a/test/openssl/test_ossl.rb
+++ b/test/openssl/test_ossl.rb
@@ -24,6 +24,16 @@ class OpenSSL::TestOSSL < OpenSSL::TestCase
     assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "bbbb") }
   end
 
+  def test_fixed_length_secure_compare_uaf
+    str1 = "A" * 1000000
+    evil_obj = Object.new
+    evil_obj.define_singleton_method(:to_str) do
+      str1.replace("C" * 1000000)
+      "B" * 1000000
+    end
+    assert_false(OpenSSL.fixed_length_secure_compare(str1, evil_obj))
+  end
+
   def test_secure_compare
     assert_false(OpenSSL.secure_compare("aaa", "a"))
     assert_false(OpenSSL.secure_compare("aaa", "aa"))
diff --git a/test/openssl/test_pkey_rsa.rb b/test/openssl/test_pkey_rsa.rb
index 86f51cf438..1716aef380 100644
--- a/test/openssl/test_pkey_rsa.rb
+++ b/test/openssl/test_pkey_rsa.rb
@@ -462,54 +462,54 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
 
   def test_private_encoding_encrypted
     rsa = Fixtures.pkey("rsa2048")
-    encoded = rsa.private_to_der("aes-128-cbc", "abcdef")
+    encoded = rsa.private_to_der("aes-128-cbc", "abcdefgh")
     asn1 = OpenSSL::ASN1.decode(encoded) # PKCS #8 EncryptedPrivateKeyInfo
     assert_kind_of OpenSSL::ASN1::Sequence, asn1
     assert_equal 2, asn1.value.size
     assert_not_equal rsa.private_to_der, encoded
-    assert_same_rsa rsa, OpenSSL::PKey.read(encoded, "abcdef")
-    assert_same_rsa rsa, OpenSSL::PKey.read(encoded) { "abcdef" }
+    assert_same_rsa rsa, OpenSSL::PKey.read(encoded, "abcdefgh")
+    assert_same_rsa rsa, OpenSSL::PKey.read(encoded) { "abcdefgh" }
     assert_raise(OpenSSL::PKey::PKeyError) { OpenSSL::PKey.read(encoded, "abcxyz") }
 
-    encoded = rsa.private_to_pem("aes-128-cbc", "abcdef")
+    encoded = rsa.private_to_pem("aes-128-cbc", "abcdefgh")
     assert_match (/BEGIN ENCRYPTED PRIVATE KEY/), encoded.lines[0]
-    assert_same_rsa rsa, OpenSSL::PKey.read(encoded, "abcdef")
+    assert_same_rsa rsa, OpenSSL::PKey.read(encoded, "abcdefgh")
 
     # Use openssl instead of certtool due to https://gitlab.com/gnutls/gnutls/-/issues/1632
-    # openssl pkcs8 -in test/openssl/fixtures/pkey/rsa2048.pem -topk8 -v2 aes-128-cbc -passout pass:abcdef
+    # openssl pkcs8 -in test/openssl/fixtures/pkey/rsa2048.pem -topk8 -v2 aes-128-cbc -passout pass:abcdefgh
     pem = <<~EOF
-    -----BEGIN ENCRYPTED PRIVATE KEY-----
-    MIIFLTBXBgkqhkiG9w0BBQ0wSjApBgkqhkiG9w0BBQwwHAQIay5V8CDQi5oCAggA
-    MAwGCCqGSIb3DQIJBQAwHQYJYIZIAWUDBAECBBB6eyagcbsvdQlM1kPcH7kiBIIE
-    0Ng1apIyoPAZ4BfC4kMNeSmeAv3XspxqYi3uWzXiNyTcoE6390swrwM6WvdpXvLI
-    /n/V06krxPZ9X4fBG2kLUzXt5f09lEvmQU1HW1wJGU5Sq3bNeXBrlJF4DzJE4WWd
-    whVVvNMm44ghdzN/jGSw3z+6d717N+waa7vrpBDsHjhsPNwxpyzUvcFPFysTazxx
-    kN/dziIBF6SRKi6w8VaJEMQ8czGu5T3jOc2e/1p3/AYhHLPS4NHhLR5OUh0TKqLK
-    tANAqI9YqCAjhqcYCmN3mMQXY52VfOqG9hlX1x9ZQyqiH7l102EWbPqouk6bCBLQ
-    wHepPg4uK99Wsdh65qEryNnXQ5ZmO6aGb6T3TFENCaNKmi8Nh+/5dr7J7YfhIwpo
-    FqHvk0hrZ8r3EQlr8/td0Yb1/IKzeQ34638uXf9UxK7C6o+ilsmJDR4PHJUfZL23
-    Yb9qWJ0GEzd5AMsI7x6KuUxSuH9nKniv5Tzyty3Xmb4FwXUyADWE19cVuaT+HrFz
-    GraKnA3UXbEgWAU48/l4K2HcAHyHDD2Kbp8k+o1zUkH0fWUdfE6OUGtx19Fv44Jh
-    B7xDngK8K48C6nrj06/DSYfXlb2X7WQiapeG4jt6U57tLH2XAjHCkvu0IBZ+//+P
-    yIWduEHQ3w8FBRcIsTNJo5CjkGk580TVQB/OBLWfX48Ay3oF9zgnomDIlVjl9D0n
-    lKxw/KMCLkvB78rUeGbr1Kwj36FhGpTBw3FgcYGa5oWFZTlcOgMTXLqlbb9JnDlA
-    Zs7Tu0WTyOTV/Dne9nEm39Dzu6wRojiIpmygTD4FI7rmOy3CYNvL3XPv7XQj0hny
-    Ee/fLxugYlQnwPZSqOVEQY2HsG7AmEHRsvy4bIWIGt+yzAPZixt9MUdJh91ttRt7
-    QA/8J1pAsGqEuQpF6UUINZop3J7twfhO4zWYN/NNQ52eWNX2KLfjfGRhrvatzmZ0
-    BuCsCI9hwEeE6PTlhbX1Rs177MrDc3vlqz2V3Po0OrFjXAyg9DR/OC4iK5wOG2ZD
-    7StVSP8bzwQXsz3fJ0ardKXgnU2YDAP6Vykjgt+nFI09HV/S2faOc2g/UK4Y2khl
-    J93u/GHMz/Kr3bKWGY1/6nPdIdFheQjsiNhd5gI4tWik2B3QwU9mETToZ2LSvDHU
-    jYCys576xJLkdMM6nJdq72z4tCoES9IxyHVs4uLjHKIo/ZtKr+8xDo8IL4ax3U8+
-    NMhs/lwReHmPGahm1fu9zLRbNCVL7e0zrOqbjvKcSEftObpV/LLcPYXtEm+lZcck
-    /PMw49HSE364anKEXCH1cyVWJwdZRpFUHvRpLIrpHru7/cthhiEMdLgK1/x8sLob
-    DiyieLxH1DPeXT4X+z94ER4IuPVOcV5AXc/omghispEX6DNUnn5jC4e3WyabjUbw
-    MuO9lVH9Wi2/ynExCqVmQkdbTXuLwjni1fJ27Q5zb0aCmhO8eq6P869NCjhJuiUj
-    NI9XtGLP50YVWE0kL8KEJqnyFudky8Khzk4/dyixQFqin5GfT4vetrLunGHy7lRB
-    3LpnFrpMOr+0xr1RW1k9vlmjRsJSiojJfReYO7gH3B5swiww2azogoL+4jhF1Jxh
-    OYLWdkKhP2jSVGqtIDtny0O4lBm2+hLpWjiI0mJQ7wdA
-    -----END ENCRYPTED PRIVATE KEY-----
+-----BEGIN ENCRYPTED PRIVATE KEY-----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+-----END ENCRYPTED PRIVATE KEY-----
     EOF
-    assert_same_rsa rsa, OpenSSL::PKey.read(pem, "abcdef")
+    assert_same_rsa rsa, OpenSSL::PKey.read(pem, "abcdefgh")
   end
 
   def test_params
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index ce1b2c1e96..e4fd581079 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -1909,7 +1909,9 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
       }
     }
     start_server(ctx_proc: ctx_proc) do |port|
-      server_connect(port) { |ssl|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.groups = "P-256" # Exclude RFC 7919 groups
+      server_connect(port, ctx) { |ssl|
         assert called, "dh callback should be called"
         assert_equal dh.to_der, ssl.tmp_key.to_der
       }
@@ -2172,7 +2174,9 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
       ctx.tmp_dh = dh
     }
     start_server(ctx_proc: ctx_proc) do |port|
-      server_connect(port) { |ssl|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.groups = "P-256" # Exclude RFC 7919 groups
+      server_connect(port, ctx) { |ssl|
         assert_equal dh.to_der, ssl.tmp_key.to_der
       }
     end
-- 
cgit v1.2.3