Merge openssl-3.2.4ruby_3_3

The changes can be found at:

    https://github.com/ruby/openssl/compare/v3.2.3...v3.2.4

25 files changed, 383 insertions, 138 deletions

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index f7ef59aa85..daadc41866 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,3 +1,13 @@
+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/depend b/ext/openssl/depend
index 0d03c85b80..a9668f48c4 100644
--- a/ext/openssl/depend
+++ b/ext/openssl/depend
@@ -1,6 +1,162 @@
 # AUTOGENERATED DEPENDENCIES START
 openssl_missing.o: $(RUBY_EXTCONF_H)
 openssl_missing.o: $(arch_hdrdir)/ruby/config.h
+openssl_missing.o: $(hdrdir)/ruby.h
+openssl_missing.o: $(hdrdir)/ruby/assert.h
+openssl_missing.o: $(hdrdir)/ruby/backward.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/assume.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/attributes.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/bool.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/inttypes.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/limits.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/long_long.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/stdalign.h
+openssl_missing.o: $(hdrdir)/ruby/backward/2/stdarg.h
+openssl_missing.o: $(hdrdir)/ruby/defines.h
+openssl_missing.o: $(hdrdir)/ruby/intern.h
+openssl_missing.o: $(hdrdir)/ruby/internal/abi.h
+openssl_missing.o: $(hdrdir)/ruby/internal/anyargs.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/char.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/double.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/fixnum.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/gid_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/int.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/intptr_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/long.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/long_long.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/mode_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/off_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/pid_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/short.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/size_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/st_data_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/arithmetic/uid_t.h
+openssl_missing.o: $(hdrdir)/ruby/internal/assume.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/alloc_size.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/artificial.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/cold.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/const.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/constexpr.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/deprecated.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/diagnose_if.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/enum_extensibility.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/error.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/flag_enum.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/forceinline.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/format.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/maybe_unused.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/noalias.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/nodiscard.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/noexcept.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/noinline.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/nonnull.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/noreturn.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/packed_struct.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/pure.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/restrict.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/returns_nonnull.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/warning.h
+openssl_missing.o: $(hdrdir)/ruby/internal/attr/weakref.h
+openssl_missing.o: $(hdrdir)/ruby/internal/cast.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is/apple.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is/clang.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is/gcc.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is/intel.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is/msvc.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_is/sunpro.h
+openssl_missing.o: $(hdrdir)/ruby/internal/compiler_since.h
+openssl_missing.o: $(hdrdir)/ruby/internal/config.h
+openssl_missing.o: $(hdrdir)/ruby/internal/constant_p.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rarray.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rbasic.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rbignum.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rclass.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rdata.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rfile.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rhash.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/robject.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rregexp.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rstring.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rstruct.h
+openssl_missing.o: $(hdrdir)/ruby/internal/core/rtypeddata.h
+openssl_missing.o: $(hdrdir)/ruby/internal/ctype.h
+openssl_missing.o: $(hdrdir)/ruby/internal/dllexport.h
+openssl_missing.o: $(hdrdir)/ruby/internal/dosish.h
+openssl_missing.o: $(hdrdir)/ruby/internal/error.h
+openssl_missing.o: $(hdrdir)/ruby/internal/eval.h
+openssl_missing.o: $(hdrdir)/ruby/internal/event.h
+openssl_missing.o: $(hdrdir)/ruby/internal/fl_type.h
+openssl_missing.o: $(hdrdir)/ruby/internal/gc.h
+openssl_missing.o: $(hdrdir)/ruby/internal/glob.h
+openssl_missing.o: $(hdrdir)/ruby/internal/globals.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/attribute.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/builtin.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/c_attribute.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/cpp_attribute.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/declspec_attribute.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/extension.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/feature.h
+openssl_missing.o: $(hdrdir)/ruby/internal/has/warning.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/array.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/bignum.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/class.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/compar.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/complex.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/cont.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/dir.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/enum.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/enumerator.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/error.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/eval.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/file.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/hash.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/io.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/load.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/marshal.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/numeric.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/object.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/parse.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/proc.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/process.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/random.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/range.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/rational.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/re.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/ruby.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/select.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/select/largesize.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/signal.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/sprintf.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/string.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/struct.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/thread.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/time.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/variable.h
+openssl_missing.o: $(hdrdir)/ruby/internal/intern/vm.h
+openssl_missing.o: $(hdrdir)/ruby/internal/interpreter.h
+openssl_missing.o: $(hdrdir)/ruby/internal/iterator.h
+openssl_missing.o: $(hdrdir)/ruby/internal/memory.h
+openssl_missing.o: $(hdrdir)/ruby/internal/method.h
+openssl_missing.o: $(hdrdir)/ruby/internal/module.h
+openssl_missing.o: $(hdrdir)/ruby/internal/newobj.h
+openssl_missing.o: $(hdrdir)/ruby/internal/scan_args.h
+openssl_missing.o: $(hdrdir)/ruby/internal/special_consts.h
+openssl_missing.o: $(hdrdir)/ruby/internal/static_assert.h
+openssl_missing.o: $(hdrdir)/ruby/internal/stdalign.h
+openssl_missing.o: $(hdrdir)/ruby/internal/stdbool.h
+openssl_missing.o: $(hdrdir)/ruby/internal/symbol.h
+openssl_missing.o: $(hdrdir)/ruby/internal/value.h
+openssl_missing.o: $(hdrdir)/ruby/internal/value_type.h
+openssl_missing.o: $(hdrdir)/ruby/internal/variable.h
+openssl_missing.o: $(hdrdir)/ruby/internal/warning_push.h
+openssl_missing.o: $(hdrdir)/ruby/internal/xmalloc.h
+openssl_missing.o: $(hdrdir)/ruby/missing.h
+openssl_missing.o: $(hdrdir)/ruby/ruby.h
+openssl_missing.o: $(hdrdir)/ruby/st.h
+openssl_missing.o: $(hdrdir)/ruby/subst.h
 openssl_missing.o: openssl_missing.c
 openssl_missing.o: openssl_missing.h
 ossl.o: $(RUBY_EXTCONF_H)
diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index 56f4a1c3ab..0de00b62a0 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -13,14 +13,7 @@
 
 require "mkmf"
 
-ssl_dirs = nil
-if defined?(::TruffleRuby)
-  # Always respect the openssl prefix chosen by truffle/openssl-prefix
-  require 'truffle/openssl-prefix'
-  ssl_dirs = dir_config("openssl", ENV["OPENSSL_PREFIX"])
-else
-  ssl_dirs = dir_config("openssl")
-end
+ssl_dirs = dir_config("openssl")
 dir_config_given = ssl_dirs.any?
 
 _, ssl_ldir = ssl_dirs
@@ -193,6 +186,7 @@ have_func("TS_VERIFY_CTX_add_flags(NULL, 0)", ts_h)
 have_func("TS_RESP_CTX_set_time_cb(NULL, NULL, NULL)", ts_h)
 have_func("EVP_PBE_scrypt(\"\", 0, (unsigned char *)\"\", 0, 0, 0, 0, 0, NULL, 0)", evp_h)
 have_func("SSL_CTX_set_post_handshake_auth(NULL, 0)", ssl_h)
+have_func("ASN1_STRING_get0_data(NULL)", "openssl/asn1.h")
 
 # added in 1.1.1
 have_func("EVP_PKEY_check(NULL)", evp_h)
@@ -210,6 +204,9 @@ have_func("EVP_MD_CTX_get_pkey_ctx(NULL)", evp_h)
 have_func("EVP_PKEY_eq(NULL, NULL)", evp_h)
 have_func("EVP_PKEY_dup(NULL)", evp_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 63a404af9e..ca073a20ae 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 = "3.2.3"
+  VERSION = "3.2.4"
 end
diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
index cf42192384..1311fedc42 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       = "3.2.3"
+  spec.version       = "3.2.4"
   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.c b/ext/openssl/openssl_missing.c
index 4415703db4..59dbec6fc3 100644
--- a/ext/openssl/openssl_missing.c
+++ b/ext/openssl/openssl_missing.c
@@ -8,6 +8,7 @@
  * (See the file 'LICENCE'.)
  */
 #include RUBY_EXTCONF_H
+#include <ruby.h>
 
 #include <string.h> /* memcpy() */
 #include <openssl/x509_vfy.h>
diff --git a/ext/openssl/openssl_missing.h b/ext/openssl/openssl_missing.h
index 8629bfe505..9ddb5c8f04 100644
--- a/ext/openssl/openssl_missing.h
+++ b/ext/openssl/openssl_missing.h
@@ -210,6 +210,10 @@ IMPL_PKEY_GETTER(EC_KEY, ec)
     } while (0)
 #endif
 
+#if !defined(HAVE_ASN1_STRING_GET0_DATA)
+#  define ASN1_STRING_get0_data(x) ((x)->data)
+#endif
+
 /* added in 3.0.0 */
 #if !defined(HAVE_TS_VERIFY_CTX_SET_CERTS)
 #  define TS_VERIFY_CTX_set_certs(ctx, crts) TS_VERIFY_CTS_set_certs(ctx, crts)
@@ -235,4 +239,27 @@ IMPL_PKEY_GETTER(EC_KEY, ec)
 #  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 00eded55cb..ce74c0e0af 100644
--- a/ext/openssl/ossl.c
+++ b/ext/openssl/ossl.c
@@ -136,7 +136,7 @@ ossl_buf2str(char *buf, int len)
 }
 
 void
-ossl_bin2hex(unsigned char *in, char *out, size_t inlen)
+ossl_bin2hex(const unsigned char *in, char *out, size_t inlen)
 {
     const char *hex = "0123456789abcdef";
     size_t i;
diff --git a/ext/openssl/ossl.h b/ext/openssl/ossl.h
index 68d42b71e2..4d364c1f30 100644
--- a/ext/openssl/ossl.h
+++ b/ext/openssl/ossl.h
@@ -64,6 +64,7 @@
 
 #if OSSL_OPENSSL_PREREQ(3, 0, 0)
 # define OSSL_USE_PROVIDER
+# include <openssl/provider.h>
 #endif
 
 /*
@@ -119,7 +120,7 @@ do{\
  * Convert binary string to hex string. The caller is responsible for
  * ensuring out has (2 * len) bytes of capacity.
  */
-void ossl_bin2hex(unsigned char *in, char *out, size_t len);
+void ossl_bin2hex(const unsigned char *in, char *out, size_t len);
 
 /*
  * Our default PEM callback
diff --git a/ext/openssl/ossl_asn1.c b/ext/openssl/ossl_asn1.c
index f26a4759cf..3579321383 100644
--- a/ext/openssl/ossl_asn1.c
+++ b/ext/openssl/ossl_asn1.c
@@ -17,17 +17,18 @@ static VALUE ossl_asn1_initialize(int argc, VALUE *argv, VALUE self);
  * DATE conversion
  */
 VALUE
-asn1time_to_time(const ASN1_TIME *time)
+asn1time_to_time(const ASN1_TIME *time_)
 {
+    ASN1_TIME *time = (ASN1_TIME *)time_; // const cast for OpenSSL 1.0.2
     struct tm tm;
     VALUE argv[6];
     int count;
 
     memset(&tm, 0, sizeof(struct tm));
 
-    switch (time->type) {
+    switch (ASN1_STRING_type(time)) {
     case V_ASN1_UTCTIME:
-	count = sscanf((const char *)time->data, "%2d%2d%2d%2d%2d%2dZ",
+	count = sscanf((const char *)ASN1_STRING_get0_data(time), "%2d%2d%2d%2d%2d%2dZ",
 		&tm.tm_year, &tm.tm_mon, &tm.tm_mday, &tm.tm_hour, &tm.tm_min,
 		&tm.tm_sec);
 
@@ -35,7 +36,7 @@ asn1time_to_time(const ASN1_TIME *time)
 	    tm.tm_sec = 0;
 	} else if (count != 6) {
 	    ossl_raise(rb_eTypeError, "bad UTCTIME format: \"%s\"",
-		    time->data);
+		    ASN1_STRING_get0_data(time));
 	}
 	if (tm.tm_year < 69) {
 	    tm.tm_year += 2000;
@@ -44,7 +45,7 @@ asn1time_to_time(const ASN1_TIME *time)
 	}
 	break;
     case V_ASN1_GENERALIZEDTIME:
-	count = sscanf((const char *)time->data, "%4d%2d%2d%2d%2d%2dZ",
+	count = sscanf((const char *)ASN1_STRING_get0_data(time), "%4d%2d%2d%2d%2d%2dZ",
 		&tm.tm_year, &tm.tm_mon, &tm.tm_mday, &tm.tm_hour, &tm.tm_min,
 		&tm.tm_sec);
 	if (count == 5) {
@@ -52,7 +53,7 @@ asn1time_to_time(const ASN1_TIME *time)
 	}
 	else if (count != 6) {
 		ossl_raise(rb_eTypeError, "bad GENERALIZEDTIME format: \"%s\"",
-			time->data);
+			ASN1_STRING_get0_data(time));
 	}
 	break;
     default:
@@ -97,7 +98,8 @@ ossl_time_split(VALUE time, time_t *sec, int *days)
 VALUE
 asn1str_to_str(const ASN1_STRING *str)
 {
-    return rb_str_new((const char *)str->data, str->length);
+    return rb_str_new((const char *)ASN1_STRING_get0_data(str),
+                      ASN1_STRING_length(str));
 }
 
 /*
@@ -112,9 +114,9 @@ asn1integer_to_num(const ASN1_INTEGER *ai)
     if (!ai) {
 	ossl_raise(rb_eTypeError, "ASN1_INTEGER is NULL!");
     }
-    if (ai->type == V_ASN1_ENUMERATED)
-	/* const_cast: workaround for old OpenSSL */
-	bn = ASN1_ENUMERATED_to_BN((ASN1_ENUMERATED *)ai, NULL);
+    if (ASN1_STRING_type((ASN1_STRING *)ai) == V_ASN1_ENUMERATED)
+        /* const_cast: workaround for old OpenSSL */
+        bn = ASN1_ENUMERATED_to_BN((ASN1_ENUMERATED *)ai, NULL);
     else
 	bn = ASN1_INTEGER_to_BN(ai, NULL);
 
@@ -210,7 +212,7 @@ 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;
 
@@ -218,11 +220,11 @@ 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;
 }
@@ -346,22 +348,25 @@ 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;
 }
@@ -746,7 +751,7 @@ 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;
 
@@ -793,18 +798,18 @@ int_ossl_asn1_decode0_prim(unsigned char **pp, long length, long hlen, int tag,
     *num_read = hlen + length;
 
     if (tc == sym_UNIVERSAL &&
-	tag < ossl_asn1_info_size && ossl_asn1_info[tag].klass) {
-	VALUE klass = *ossl_asn1_info[tag].klass;
-	VALUE args[4];
-	args[0] = value;
-	args[1] = INT2NUM(tag);
-	args[2] = Qnil;
-	args[3] = tc;
-	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));
-	}
+        tag < ossl_asn1_info_size && ossl_asn1_info[tag].klass) {
+        VALUE klass = *ossl_asn1_info[tag].klass;
+        VALUE args[4];
+        args[0] = value;
+        args[1] = INT2NUM(tag);
+        args[2] = Qnil;
+        args[3] = tc;
+        asn1data = rb_obj_alloc(klass);
+        ossl_asn1_initialize(4, args, asn1data);
+        if(tag == V_ASN1_BIT_STRING){
+            rb_ivar_set(asn1data, sivUNUSED_BITS, INT2NUM(flag));
+        }
     }
     else {
 	asn1data = rb_obj_alloc(cASN1Data);
diff --git a/ext/openssl/ossl_ns_spki.c b/ext/openssl/ossl_ns_spki.c
index 9bed1f330e..ac9937eaa8 100644
--- a/ext/openssl/ossl_ns_spki.c
+++ b/ext/openssl/ossl_ns_spki.c
@@ -230,13 +230,12 @@ ossl_spki_get_challenge(VALUE self)
     NETSCAPE_SPKI *spki;
 
     GetSPKI(self, spki);
-    if (spki->spkac->challenge->length <= 0) {
-	OSSL_Debug("Challenge.length <= 0?");
-	return rb_str_new(0, 0);
+    if (ASN1_STRING_length(spki->spkac->challenge) <= 0) {
+        OSSL_Debug("Challenge.length <= 0?");
+        return rb_str_new(0, 0);
     }
 
-    return rb_str_new((const char *)spki->spkac->challenge->data,
-		      spki->spkac->challenge->length);
+    return asn1str_to_str(spki->spkac->challenge);
 }
 
 /*
diff --git a/ext/openssl/ossl_ocsp.c b/ext/openssl/ossl_ocsp.c
index df986bb3ee..b4b326fbd1 100644
--- a/ext/openssl/ossl_ocsp.c
+++ b/ext/openssl/ossl_ocsp.c
@@ -900,7 +900,6 @@ ossl_ocspbres_get_status(VALUE self)
     OCSP_CERTID *cid;
     ASN1_TIME *revtime, *thisupd, *nextupd;
     int status, reason;
-    X509_EXTENSION *x509ext;
     VALUE ret, ary, ext;
     int count, ext_count, i, j;
 
@@ -927,7 +926,7 @@ ossl_ocspbres_get_status(VALUE self)
 	ext = rb_ary_new();
 	ext_count = OCSP_SINGLERESP_get_ext_count(single);
 	for(j = 0; j < ext_count; j++){
-	    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);
@@ -1358,7 +1357,6 @@ static VALUE
 ossl_ocspsres_get_extensions(VALUE self)
 {
     OCSP_SINGLERESP *sres;
-    X509_EXTENSION *ext;
     int count, i;
     VALUE ary;
 
@@ -1367,7 +1365,7 @@ 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 */
     }
 
@@ -1565,8 +1563,9 @@ ossl_ocspcid_get_issuer_name_hash(VALUE self)
     GetOCSPCertId(self, id);
     OCSP_id_get0_info(&name_hash, NULL, NULL, NULL, id);
 
-    ret = rb_str_new(NULL, name_hash->length * 2);
-    ossl_bin2hex(name_hash->data, RSTRING_PTR(ret), name_hash->length);
+    ret = rb_str_new(NULL, ASN1_STRING_length(name_hash) * 2);
+    ossl_bin2hex(ASN1_STRING_get0_data(name_hash), RSTRING_PTR(ret),
+                 ASN1_STRING_length(name_hash));
 
     return ret;
 }
@@ -1588,8 +1587,9 @@ ossl_ocspcid_get_issuer_key_hash(VALUE self)
     GetOCSPCertId(self, id);
     OCSP_id_get0_info(NULL, NULL, &key_hash, NULL, id);
 
-    ret = rb_str_new(NULL, key_hash->length * 2);
-    ossl_bin2hex(key_hash->data, RSTRING_PTR(ret), key_hash->length);
+    ret = rb_str_new(NULL, ASN1_STRING_length(key_hash) * 2);
+    ossl_bin2hex(ASN1_STRING_get0_data(key_hash), RSTRING_PTR(ret),
+                 ASN1_STRING_length(key_hash));
 
     return ret;
 }
diff --git a/ext/openssl/ossl_pkcs7.c b/ext/openssl/ossl_pkcs7.c
index 7e5fb9c1b2..41ace21d27 100644
--- a/ext/openssl/ossl_pkcs7.c
+++ b/ext/openssl/ossl_pkcs7.c
@@ -932,7 +932,7 @@ static VALUE
 ossl_pkcs7si_get_signed_time(VALUE self)
 {
     PKCS7_SIGNER_INFO *p7si;
-    ASN1_TYPE *asn1obj;
+    const ASN1_TYPE *asn1obj;
 
     GetPKCS7si(self, p7si);
 
diff --git a/ext/openssl/ossl_pkey.c b/ext/openssl/ossl_pkey.c
index 9e0835d38c..c579135bde 100644
--- a/ext/openssl/ossl_pkey.c
+++ b/ext/openssl/ossl_pkey.c
@@ -636,6 +636,30 @@ ossl_pkey_initialize_copy(VALUE self, VALUE other)
 #endif
 
 #ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+
+#ifndef OSSL_USE_PROVIDER
+static int
+lookup_pkey_type(VALUE type)
+{
+    const EVP_PKEY_ASN1_METHOD *ameth;
+    int pkey_id;
+
+    StringValue(type);
+    /*
+     * XXX: EVP_PKEY_asn1_find_str() looks up a PEM type string. Should we use
+     * OBJ_txt2nid() instead (and then somehow check if the NID is an acceptable
+     * EVP_PKEY type)?
+     * It is probably fine, though, since it can handle all algorithms that
+     * support raw keys in 1.1.1: { X25519, X448, ED25519, ED448, HMAC }.
+     */
+    ameth = EVP_PKEY_asn1_find_str(NULL, RSTRING_PTR(type), RSTRING_LENINT(type));
+    if (!ameth)
+        ossl_raise(ePKeyError, "algorithm %"PRIsVALUE" not found", type);
+    EVP_PKEY_asn1_get0_info(&pkey_id, NULL, NULL, NULL, NULL, ameth);
+    return pkey_id;
+}
+#endif
+
 /*
  *  call-seq:
  *      OpenSSL::PKey.new_raw_private_key(algo, string) -> PKey
@@ -647,22 +671,23 @@ static VALUE
 ossl_pkey_new_raw_private_key(VALUE self, VALUE type, VALUE key)
 {
     EVP_PKEY *pkey;
-    const EVP_PKEY_ASN1_METHOD *ameth;
-    int pkey_id;
     size_t keylen;
 
-    StringValue(type);
     StringValue(key);
-    ameth = EVP_PKEY_asn1_find_str(NULL, RSTRING_PTR(type), RSTRING_LENINT(type));
-    if (!ameth)
-        ossl_raise(ePKeyError, "algorithm %"PRIsVALUE" not found", type);
-    EVP_PKEY_asn1_get0_info(&pkey_id, NULL, NULL, NULL, NULL, ameth);
-
     keylen = RSTRING_LEN(key);
 
+#ifdef OSSL_USE_PROVIDER
+    pkey = EVP_PKEY_new_raw_private_key_ex(NULL, StringValueCStr(type), NULL,
+                                           (unsigned char *)RSTRING_PTR(key),
+                                           keylen);
+    if (!pkey)
+        ossl_raise(ePKeyError, "EVP_PKEY_new_raw_private_key_ex");
+#else
+    int pkey_id = lookup_pkey_type(type);
     pkey = EVP_PKEY_new_raw_private_key(pkey_id, NULL, (unsigned char *)RSTRING_PTR(key), keylen);
     if (!pkey)
         ossl_raise(ePKeyError, "EVP_PKEY_new_raw_private_key");
+#endif
 
     return ossl_pkey_new(pkey);
 }
@@ -680,22 +705,23 @@ static VALUE
 ossl_pkey_new_raw_public_key(VALUE self, VALUE type, VALUE key)
 {
     EVP_PKEY *pkey;
-    const EVP_PKEY_ASN1_METHOD *ameth;
-    int pkey_id;
     size_t keylen;
 
-    StringValue(type);
     StringValue(key);
-    ameth = EVP_PKEY_asn1_find_str(NULL, RSTRING_PTR(type), RSTRING_LENINT(type));
-    if (!ameth)
-        ossl_raise(ePKeyError, "algorithm %"PRIsVALUE" not found", type);
-    EVP_PKEY_asn1_get0_info(&pkey_id, NULL, NULL, NULL, NULL, ameth);
-
     keylen = RSTRING_LEN(key);
 
+#ifdef OSSL_USE_PROVIDER
+    pkey = EVP_PKEY_new_raw_public_key_ex(NULL, StringValueCStr(type), NULL,
+                                          (unsigned char *)RSTRING_PTR(key),
+                                          keylen);
+    if (!pkey)
+        ossl_raise(ePKeyError, "EVP_PKEY_new_raw_public_key_ex");
+#else
+    int pkey_id = lookup_pkey_type(type);
     pkey = EVP_PKEY_new_raw_public_key(pkey_id, NULL, (unsigned char *)RSTRING_PTR(key), keylen);
     if (!pkey)
         ossl_raise(ePKeyError, "EVP_PKEY_new_raw_public_key");
+#endif
 
     return ossl_pkey_new(pkey);
 }
@@ -715,6 +741,10 @@ ossl_pkey_oid(VALUE self)
 
     GetPKey(self, pkey);
     nid = EVP_PKEY_id(pkey);
+#ifdef OSSL_USE_PROVIDER
+    if (nid == EVP_PKEY_KEYMGMT)
+        ossl_raise(ePKeyError, "EVP_PKEY_id");
+#endif
     return rb_str_new_cstr(OBJ_nid2sn(nid));
 }
 
@@ -728,13 +758,23 @@ static VALUE
 ossl_pkey_inspect(VALUE self)
 {
     EVP_PKEY *pkey;
-    int nid;
 
     GetPKey(self, pkey);
-    nid = EVP_PKEY_id(pkey);
-    return rb_sprintf("#<%"PRIsVALUE":%p oid=%s>",
-                      rb_class_name(CLASS_OF(self)), (void *)self,
-                      OBJ_nid2sn(nid));
+    VALUE str = rb_sprintf("#<%"PRIsVALUE":%p",
+                           rb_obj_class(self), (void *)self);
+    int nid = EVP_PKEY_id(pkey);
+#ifdef OSSL_USE_PROVIDER
+    if (nid != EVP_PKEY_KEYMGMT)
+#endif
+    rb_str_catf(str, " oid=%s", OBJ_nid2sn(nid));
+#ifdef OSSL_USE_PROVIDER
+    rb_str_catf(str, " type_name=%s", EVP_PKEY_get0_type_name(pkey));
+    const OSSL_PROVIDER *prov = EVP_PKEY_get0_provider(pkey);
+    if (prov)
+        rb_str_catf(str, " provider=%s", OSSL_PROVIDER_get0_name(prov));
+#endif
+    rb_str_catf(str, ">");
+    return str;
 }
 
 /*
diff --git a/ext/openssl/ossl_provider.c b/ext/openssl/ossl_provider.c
index 981c6ccdc7..6ec8187990 100644
--- a/ext/openssl/ossl_provider.c
+++ b/ext/openssl/ossl_provider.c
@@ -5,8 +5,6 @@
 #include "ossl.h"
 
 #ifdef OSSL_USE_PROVIDER
-# include <openssl/provider.h>
-
 #define NewProvider(klass) \
     TypedData_Wrap_Struct((klass), &ossl_provider_type, 0)
 #define SetProvider(obj, provider) do { \
diff --git a/ext/openssl/ossl_ts.c b/ext/openssl/ossl_ts.c
index f698bdc7ff..7d01b0b8ba 100644
--- a/ext/openssl/ossl_ts.c
+++ b/ext/openssl/ossl_ts.c
@@ -288,7 +288,7 @@ ossl_ts_req_get_msg_imprint(VALUE self)
     mi = TS_REQ_get_msg_imprint(req);
     hashed_msg = TS_MSG_IMPRINT_get_msg(mi);
 
-    ret = rb_str_new((const char *)hashed_msg->data, hashed_msg->length);
+    ret = asn1str_to_str(hashed_msg);
 
     return ret;
 }
@@ -497,7 +497,7 @@ ossl_ts_req_to_der(VALUE self)
         ossl_raise(eTimestampError, "Message imprint missing algorithm");
 
     hashed_msg = TS_MSG_IMPRINT_get_msg(mi);
-    if (!hashed_msg->length)
+    if (!ASN1_STRING_length(hashed_msg))
         ossl_raise(eTimestampError, "Message imprint missing hashed message");
 
     return asn1_to_der((void *)req, (int (*)(void *, unsigned char **))i2d_TS_REQ);
@@ -730,7 +730,7 @@ 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)))
@@ -974,7 +974,7 @@ ossl_ts_token_info_get_msg_imprint(VALUE self)
     GetTSTokenInfo(self, info);
     mi = TS_TST_INFO_get_msg_imprint(info);
     hashed_msg = TS_MSG_IMPRINT_get_msg(mi);
-    ret = rb_str_new((const char *)hashed_msg->data, hashed_msg->length);
+    ret = asn1str_to_str(hashed_msg);
 
     return ret;
 }
diff --git a/ext/openssl/ossl_x509.h b/ext/openssl/ossl_x509.h
index 4fadfa6b82..7448ca2e7d 100644
--- a/ext/openssl/ossl_x509.h
+++ b/ext/openssl/ossl_x509.h
@@ -30,7 +30,7 @@ void Init_ossl_x509(void);
 extern VALUE cX509Attr;
 extern VALUE eX509AttrError;
 
-VALUE ossl_x509attr_new(X509_ATTRIBUTE *);
+VALUE ossl_x509attr_new(const X509_ATTRIBUTE *);
 X509_ATTRIBUTE *GetX509AttrPtr(VALUE);
 void Init_ossl_x509attr(void);
 
@@ -40,7 +40,7 @@ void Init_ossl_x509attr(void);
 extern VALUE cX509Cert;
 extern VALUE eX509CertError;
 
-VALUE ossl_x509_new(X509 *);
+VALUE ossl_x509_new(const X509 *);
 X509 *GetX509CertPtr(VALUE);
 X509 *DupX509CertPtr(VALUE);
 void Init_ossl_x509cert(void);
@@ -51,7 +51,7 @@ void Init_ossl_x509cert(void);
 extern VALUE cX509CRL;
 extern VALUE eX509CRLError;
 
-VALUE ossl_x509crl_new(X509_CRL *);
+VALUE ossl_x509crl_new(const X509_CRL *);
 X509_CRL *GetX509CRLPtr(VALUE);
 void Init_ossl_x509crl(void);
 
@@ -62,7 +62,7 @@ extern VALUE cX509Ext;
 extern VALUE cX509ExtFactory;
 extern VALUE eX509ExtError;
 
-VALUE ossl_x509ext_new(X509_EXTENSION *);
+VALUE ossl_x509ext_new(const X509_EXTENSION *);
 X509_EXTENSION *GetX509ExtPtr(VALUE);
 void Init_ossl_x509ext(void);
 
@@ -72,7 +72,7 @@ void Init_ossl_x509ext(void);
 extern VALUE cX509Name;
 extern VALUE eX509NameError;
 
-VALUE ossl_x509name_new(X509_NAME *);
+VALUE ossl_x509name_new(const X509_NAME *);
 X509_NAME *GetX509NamePtr(VALUE);
 void Init_ossl_x509name(void);
 
@@ -91,7 +91,7 @@ void Init_ossl_x509req(void);
 extern VALUE cX509Rev;
 extern VALUE eX509RevError;
 
-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 d1d8bb5e95..0057148436 100644
--- a/ext/openssl/ossl_x509attr.c
+++ b/ext/openssl/ossl_x509attr.c
@@ -48,7 +48,7 @@ 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;
@@ -57,7 +57,8 @@ ossl_x509attr_new(X509_ATTRIBUTE *attr)
     if (!attr) {
 	new = X509_ATTRIBUTE_new();
     } else {
-	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, NULL);
@@ -174,7 +175,7 @@ static VALUE
 ossl_x509attr_get_oid(VALUE self)
 {
     X509_ATTRIBUTE *attr;
-    ASN1_OBJECT *oid;
+    const ASN1_OBJECT *oid;
     BIO *out;
     VALUE ret;
     int nid;
@@ -186,7 +187,7 @@ ossl_x509attr_get_oid(VALUE self)
     else{
 	if (!(out = BIO_new(BIO_s_mem())))
 	    ossl_raise(eX509AttrError, NULL);
-	i2a_ASN1_OBJECT(out, oid);
+	i2a_ASN1_OBJECT(out, (ASN1_OBJECT *)oid);
 	ret = ossl_membio2str(out);
     }
 
@@ -214,7 +215,7 @@ ossl_x509attr_set_value(VALUE self, VALUE value)
 
     GetX509Attr(self, attr);
     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)
 	    ossl_raise(eX509AttrError, NULL);
@@ -256,7 +257,7 @@ 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 aa6b9bb7ce..2727278ed0 100644
--- a/ext/openssl/ossl_x509cert.c
+++ b/ext/openssl/ossl_x509cert.c
@@ -48,7 +48,7 @@ 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;
@@ -57,7 +57,8 @@ ossl_x509_new(X509 *x509)
     if (!x509) {
 	new = X509_new();
     } else {
-	new = X509_dup(x509);
+	/* OpenSSL 1.1.1 takes a non-const pointer */
+	new = X509_dup((X509 *)x509);
     }
     if (!new) {
 	ossl_raise(eX509CertError, NULL);
@@ -351,7 +352,7 @@ 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! */
@@ -386,7 +387,7 @@ 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! */
@@ -608,7 +609,6 @@ ossl_x509_get_extensions(VALUE self)
 {
     X509 *x509;
     int count, i;
-    X509_EXTENSION *ext;
     VALUE ary;
 
     GetX509(self, x509);
@@ -618,7 +618,7 @@ ossl_x509_get_extensions(VALUE self)
     }
     ary = rb_ary_new2(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 80e29f9df2..5244a666d0 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 = crl ? X509_CRL_dup(crl) : X509_CRL_new();
+    /* OpenSSL 1.1.1 takes a non-const pointer */
+    tmp = crl ? X509_CRL_dup((X509_CRL *)crl) : X509_CRL_new();
     if(!tmp) ossl_raise(eX509CRLError, NULL);
     SetX509CRL(obj, tmp);
 
@@ -274,7 +275,7 @@ ossl_x509crl_get_revoked(VALUE self)
 {
     X509_CRL *crl;
     int i, num;
-    X509_REVOKED *rev;
+    const X509_REVOKED *rev;
     VALUE ary, revoked;
 
     GetX509CRL(self, crl);
@@ -440,7 +441,6 @@ ossl_x509crl_get_extensions(VALUE self)
 {
     X509_CRL *crl;
     int count, i;
-    X509_EXTENSION *ext;
     VALUE ary;
 
     GetX509CRL(self, crl);
@@ -451,7 +451,7 @@ ossl_x509crl_get_extensions(VALUE self)
     }
     ary = rb_ary_new2(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 192d09bd3f..b63b0c73d3 100644
--- a/ext/openssl/ossl_x509ext.c
+++ b/ext/openssl/ossl_x509ext.c
@@ -62,7 +62,7 @@ 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;
@@ -71,7 +71,8 @@ ossl_x509ext_new(X509_EXTENSION *ext)
     if (!ext) {
 	new = X509_EXTENSION_new();
     } else {
-	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, NULL);
@@ -346,12 +347,20 @@ 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))) {
-	ossl_raise(eX509ExtError, "ASN1_OCTET_STRING_set");
+                               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;
 }
@@ -371,7 +380,7 @@ static VALUE
 ossl_x509ext_get_oid(VALUE obj)
 {
     X509_EXTENSION *ext;
-    ASN1_OBJECT *extobj;
+    const ASN1_OBJECT *extobj;
     BIO *out;
     VALUE ret;
     int nid;
@@ -383,7 +392,7 @@ ossl_x509ext_get_oid(VALUE obj)
     else{
 	if (!(out = BIO_new(BIO_s_mem())))
 	    ossl_raise(eX509ExtError, NULL);
-	i2a_ASN1_OBJECT(out, extobj);
+	i2a_ASN1_OBJECT(out, (ASN1_OBJECT *)extobj);
 	ret = ossl_membio2str(out);
     }
 
@@ -411,13 +420,13 @@ 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)
 	ossl_raise(eX509ExtError, NULL);
 
-    return rb_str_new((const char *)value->data, value->length);
+    return asn1str_to_str(value);
 }
 
 static VALUE
diff --git a/ext/openssl/ossl_x509name.c b/ext/openssl/ossl_x509name.c
index 9591912f70..90ec2d96a2 100644
--- a/ext/openssl/ossl_x509name.c
+++ b/ext/openssl/ossl_x509name.c
@@ -53,7 +53,7 @@ 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;
@@ -62,7 +62,8 @@ ossl_x509name_new(X509_NAME *name)
     if (!name) {
 	new = X509_NAME_new();
     } else {
-	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, NULL);
@@ -360,7 +361,7 @@ ossl_x509name_to_a(VALUE self)
     }
     ret = rb_ary_new2(entries);
     for (i=0; i<entries; i++) {
-	if (!(entry = X509_NAME_get_entry(name, i))) {
+	if (!(entry = (X509_NAME_ENTRY *)X509_NAME_get_entry(name, i))) {
 	    ossl_raise(eX509NameError, NULL);
 	}
 	if (!i2t_ASN1_OBJECT(long_name, sizeof(long_name),
@@ -374,8 +375,9 @@ ossl_x509name_to_a(VALUE self)
 	    short_name = OBJ_nid2sn(nid);
 	    vname = rb_str_new2(short_name); /*do not free*/
 	}
-	value = X509_NAME_ENTRY_get_data(entry);
-	ary = rb_ary_new3(3, vname, asn1str_to_str(value), INT2NUM(value->type));
+	value = (ASN1_STRING *)X509_NAME_ENTRY_get_data(entry);
+	ary = rb_ary_new3(3, vname, asn1str_to_str(value),
+                          INT2NUM(ASN1_STRING_type(value)));
 	rb_ary_push(ret, ary);
     }
     return ret;
diff --git a/ext/openssl/ossl_x509req.c b/ext/openssl/ossl_x509req.c
index f058185151..ef8e0bccfa 100644
--- a/ext/openssl/ossl_x509req.c
+++ b/ext/openssl/ossl_x509req.c
@@ -230,7 +230,7 @@ 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 */
@@ -348,7 +348,7 @@ 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 108447c868..b4916d34b3 100644
--- a/ext/openssl/ossl_x509revoked.c
+++ b/ext/openssl/ossl_x509revoked.c
@@ -48,7 +48,7 @@ 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;
@@ -57,7 +57,8 @@ ossl_x509revoked_new(X509_REVOKED *rev)
     if (!rev) {
 	new = X509_REVOKED_new();
     } else {
-	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, NULL);
@@ -189,7 +190,7 @@ 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 f27381ca90..110b5934d7 100644
--- a/ext/openssl/ossl_x509store.c
+++ b/ext/openssl/ossl_x509store.c
@@ -521,10 +521,8 @@ 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);
 }
 
@@ -765,7 +763,7 @@ 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);