openssl 2.2.1 → 3.2.0

data/ext/openssl/ossl_pkey.c

@@ -9,6 +9,10 @@
  */
 #include "ossl.h"
 
+#ifdef OSSL_USE_ENGINE
+# include <openssl/engine.h>
+#endif
+
 /*
  * Classes
  */
@@ -17,64 +21,6 @@ VALUE cPKey;
 VALUE ePKeyError;
 static ID id_private_q;
 
-/*
- * callback for generating keys
- */
-static VALUE
-call_check_ints0(VALUE arg)
-{
-    rb_thread_check_ints();
-    return Qnil;
-}
-
-static void *
-call_check_ints(void *arg)
-{
-    int state;
-    rb_protect(call_check_ints0, Qnil, &state);
-    return (void *)(VALUE)state;
-}
-
-int
-ossl_generate_cb_2(int p, int n, BN_GENCB *cb)
-{
-    VALUE ary;
-    struct ossl_generate_cb_arg *arg;
-    int state;
-
-    arg = (struct ossl_generate_cb_arg *)BN_GENCB_get_arg(cb);
-    if (arg->yield) {
-	ary = rb_ary_new2(2);
-	rb_ary_store(ary, 0, INT2NUM(p));
-	rb_ary_store(ary, 1, INT2NUM(n));
-
-	/*
-	* can be break by raising exception or 'break'
-	*/
-	rb_protect(rb_yield, ary, &state);
-	if (state) {
-	    arg->state = state;
-	    return 0;
-	}
-    }
-    if (arg->interrupted) {
-	arg->interrupted = 0;
-	state = (int)(VALUE)rb_thread_call_with_gvl(call_check_ints, NULL);
-	if (state) {
-	    arg->state = state;
-	    return 0;
-	}
-    }
-    return 1;
-}
-
-void
-ossl_generate_cb_stop(void *ptr)
-{
-    struct ossl_generate_cb_arg *arg = (struct ossl_generate_cb_arg *)ptr;
-    arg->interrupted = 1;
-}
-
 static void
 ossl_evp_pkey_free(void *ptr)
 {
@@ -89,40 +35,33 @@ const rb_data_type_t ossl_evp_pkey_type = {
     {
 	0, ossl_evp_pkey_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static VALUE
-pkey_new0(EVP_PKEY *pkey)
+pkey_new0(VALUE arg)
 {
-    VALUE obj;
-    int type;
-
-    if (!pkey || (type = EVP_PKEY_base_id(pkey)) == EVP_PKEY_NONE)
-	ossl_raise(rb_eRuntimeError, "pkey is empty");
+    EVP_PKEY *pkey = (EVP_PKEY *)arg;
+    VALUE klass, obj;
 
-    switch (type) {
+    switch (EVP_PKEY_base_id(pkey)) {
 #if !defined(OPENSSL_NO_RSA)
-    case EVP_PKEY_RSA:
-	return ossl_rsa_new(pkey);
+      case EVP_PKEY_RSA: klass = cRSA; break;
 #endif
 #if !defined(OPENSSL_NO_DSA)
-    case EVP_PKEY_DSA:
-	return ossl_dsa_new(pkey);
+      case EVP_PKEY_DSA: klass = cDSA; break;
 #endif
 #if !defined(OPENSSL_NO_DH)
-    case EVP_PKEY_DH:
-	return ossl_dh_new(pkey);
+      case EVP_PKEY_DH:  klass = cDH; break;
 #endif
 #if !defined(OPENSSL_NO_EC)
-    case EVP_PKEY_EC:
-	return ossl_ec_new(pkey);
+      case EVP_PKEY_EC:  klass = cEC; break;
 #endif
-    default:
-	obj = NewPKey(cPKey);
-	SetPKey(obj, pkey);
-	return obj;
+      default:           klass = cPKey; break;
     }
+    obj = rb_obj_alloc(klass);
+    RTYPEDDATA_DATA(obj) = pkey;
+    return obj;
 }
 
 VALUE
@@ -131,7 +70,7 @@ ossl_pkey_new(EVP_PKEY *pkey)
     VALUE obj;
     int status;
 
-    obj = rb_protect((VALUE (*)(VALUE))pkey_new0, (VALUE)pkey, &status);
+    obj = rb_protect(pkey_new0, (VALUE)pkey, &status);
     if (status) {
 	EVP_PKEY_free(pkey);
 	rb_jump_tag(status);
@@ -140,6 +79,137 @@ ossl_pkey_new(EVP_PKEY *pkey)
     return obj;
 }
 
+#if OSSL_OPENSSL_PREREQ(3, 0, 0)
+# include <openssl/decoder.h>
+
+static EVP_PKEY *
+ossl_pkey_read(BIO *bio, const char *input_type, int selection, VALUE pass)
+{
+    void *ppass = (void *)pass;
+    OSSL_DECODER_CTX *dctx;
+    EVP_PKEY *pkey = NULL;
+    int pos = 0, pos2;
+
+    dctx = OSSL_DECODER_CTX_new_for_pkey(&pkey, input_type, NULL, NULL,
+                                         selection, NULL, NULL);
+    if (!dctx)
+        goto out;
+    if (OSSL_DECODER_CTX_set_pem_password_cb(dctx, ossl_pem_passwd_cb,
+                                             ppass) != 1)
+        goto out;
+    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;
+    }
+  out:
+    OSSL_BIO_reset(bio);
+    OSSL_DECODER_CTX_free(dctx);
+    return pkey;
+}
+
+EVP_PKEY *
+ossl_pkey_read_generic(BIO *bio, VALUE pass)
+{
+    EVP_PKEY *pkey = NULL;
+    /* First check DER, then check PEM. */
+    const char *input_types[] = {"DER", "PEM"};
+    int input_type_num = (int)(sizeof(input_types) / sizeof(char *));
+    /*
+     * Non-zero selections to try to decode.
+     *
+     * See EVP_PKEY_fromdata(3) - Selections to see all the selections.
+     *
+     * This is a workaround for the decoder failing to decode or returning
+     * bogus keys with selection 0, if a key management provider is different
+     * from a decoder provider. The workaround is to avoid using selection 0.
+     *
+     * Affected OpenSSL versions: >= 3.1.0, <= 3.1.2, or >= 3.0.0, <= 3.0.10
+     * Fixed OpenSSL versions: 3.2, next release of the 3.1.z and 3.0.z
+     *
+     * See https://github.com/openssl/openssl/pull/21519 for details.
+     *
+     * First check for private key formats (EVP_PKEY_KEYPAIR). 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.
+     *
+     * Note that we need to create the OSSL_DECODER_CTX variable each time when
+     * we use the different selection as a workaround.
+     * See https://github.com/openssl/openssl/issues/20657 for details.
+     */
+    int selections[] = {
+        EVP_PKEY_KEYPAIR,
+        EVP_PKEY_KEY_PARAMETERS,
+        EVP_PKEY_PUBLIC_KEY
+    };
+    int selection_num = (int)(sizeof(selections) / sizeof(int));
+    int i, j;
+
+    for (i = 0; i < input_type_num; i++) {
+        for (j = 0; j < selection_num; j++) {
+            pkey = ossl_pkey_read(bio, input_types[i], selections[j], pass);
+            if (pkey) {
+                goto out;
+            }
+        }
+    }
+  out:
+    return pkey;
+}
+#else
+EVP_PKEY *
+ossl_pkey_read_generic(BIO *bio, VALUE pass)
+{
+    void *ppass = (void *)pass;
+    EVP_PKEY *pkey;
+
+    if ((pkey = d2i_PrivateKey_bio(bio, NULL)))
+	goto out;
+    OSSL_BIO_reset(bio);
+    if ((pkey = d2i_PKCS8PrivateKey_bio(bio, NULL, ossl_pem_passwd_cb, ppass)))
+	goto out;
+    OSSL_BIO_reset(bio);
+    if ((pkey = d2i_PUBKEY_bio(bio, NULL)))
+	goto out;
+    OSSL_BIO_reset(bio);
+    /* PEM_read_bio_PrivateKey() also parses PKCS #8 formats */
+    if ((pkey = PEM_read_bio_PrivateKey(bio, NULL, ossl_pem_passwd_cb, ppass)))
+	goto out;
+    OSSL_BIO_reset(bio);
+    if ((pkey = PEM_read_bio_PUBKEY(bio, NULL, NULL, NULL)))
+	goto out;
+    OSSL_BIO_reset(bio);
+    if ((pkey = PEM_read_bio_Parameters(bio, NULL)))
+	goto out;
+
+  out:
+    return pkey;
+}
+#endif
+
 /*
  *  call-seq:
  *     OpenSSL::PKey.read(string [, pwd ]) -> PKey
@@ -149,7 +219,7 @@ ossl_pkey_new(EVP_PKEY *pkey)
  * instance of the appropriate PKey class.
  *
  * === Parameters
- * * _string+ is a DER- or PEM-encoded string containing an arbitrary private
+ * * _string_ is a DER- or PEM-encoded string containing an arbitrary private
  *   or public key.
  * * _io_ is an instance of IO containing a DER- or PEM-encoded
  *   arbitrary private or public key.
@@ -164,36 +234,283 @@ ossl_pkey_new_from_data(int argc, VALUE *argv, VALUE self)
     VALUE data, pass;
 
     rb_scan_args(argc, argv, "11", &data, &pass);
-    pass = ossl_pem_passwd_value(pass);
-
     bio = ossl_obj2bio(&data);
-    if ((pkey = d2i_PrivateKey_bio(bio, NULL)))
-	goto ok;
-    OSSL_BIO_reset(bio);
-    if ((pkey = d2i_PKCS8PrivateKey_bio(bio, NULL, ossl_pem_passwd_cb, (void *)pass)))
-	goto ok;
-    OSSL_BIO_reset(bio);
-    if ((pkey = d2i_PUBKEY_bio(bio, NULL)))
-	goto ok;
-    OSSL_BIO_reset(bio);
-    /* PEM_read_bio_PrivateKey() also parses PKCS #8 formats */
-    if ((pkey = PEM_read_bio_PrivateKey(bio, NULL, ossl_pem_passwd_cb, (void *)pass)))
-	goto ok;
-    OSSL_BIO_reset(bio);
-    if ((pkey = PEM_read_bio_PUBKEY(bio, NULL, NULL, NULL)))
-	goto ok;
-
-    BIO_free(bio);
-    ossl_raise(ePKeyError, "Could not parse PKey");
-
-ok:
+    pkey = ossl_pkey_read_generic(bio, ossl_pem_passwd_value(pass));
     BIO_free(bio);
+    if (!pkey)
+	ossl_raise(ePKeyError, "Could not parse PKey");
     return ossl_pkey_new(pkey);
 }
 
+static VALUE
+pkey_ctx_apply_options_i(RB_BLOCK_CALL_FUNC_ARGLIST(i, ctx_v))
+{
+    VALUE key = rb_ary_entry(i, 0), value = rb_ary_entry(i, 1);
+    EVP_PKEY_CTX *ctx = (EVP_PKEY_CTX *)ctx_v;
+
+    if (SYMBOL_P(key))
+        key = rb_sym2str(key);
+    value = rb_String(value);
+
+    if (EVP_PKEY_CTX_ctrl_str(ctx, StringValueCStr(key), StringValueCStr(value)) <= 0)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_ctrl_str(ctx, %+"PRIsVALUE", %+"PRIsVALUE")",
+                   key, value);
+    return Qnil;
+}
+
+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]);
+    return Qnil;
+}
+
+static void
+pkey_ctx_apply_options(EVP_PKEY_CTX *ctx, VALUE options, int *state)
+{
+    VALUE args[2];
+    args[0] = (VALUE)ctx;
+    args[1] = options;
+
+    rb_protect(pkey_ctx_apply_options0, (VALUE)args, state);
+}
+
+struct pkey_blocking_generate_arg {
+    EVP_PKEY_CTX *ctx;
+    EVP_PKEY *pkey;
+    int state;
+    unsigned int yield: 1;
+    unsigned int genparam: 1;
+    unsigned int interrupted: 1;
+};
+
+static VALUE
+pkey_gen_cb_yield(VALUE ctx_v)
+{
+    EVP_PKEY_CTX *ctx = (void *)ctx_v;
+    int i, info_num;
+    VALUE *argv;
+
+    info_num = EVP_PKEY_CTX_get_keygen_info(ctx, -1);
+    argv = ALLOCA_N(VALUE, info_num);
+    for (i = 0; i < info_num; i++)
+        argv[i] = INT2NUM(EVP_PKEY_CTX_get_keygen_info(ctx, i));
+
+    return rb_yield_values2(info_num, argv);
+}
+
+static VALUE
+call_check_ints0(VALUE arg)
+{
+    rb_thread_check_ints();
+    return Qnil;
+}
+
+static void *
+call_check_ints(void *arg)
+{
+    int state;
+    rb_protect(call_check_ints0, Qnil, &state);
+    return (void *)(VALUE)state;
+}
+
+static int
+pkey_gen_cb(EVP_PKEY_CTX *ctx)
+{
+    struct pkey_blocking_generate_arg *arg = EVP_PKEY_CTX_get_app_data(ctx);
+    int state;
+
+    if (arg->yield) {
+        rb_protect(pkey_gen_cb_yield, (VALUE)ctx, &state);
+        if (state) {
+            arg->state = state;
+            return 0;
+        }
+    }
+    if (arg->interrupted) {
+        arg->interrupted = 0;
+        state = (int)(VALUE)rb_thread_call_with_gvl(call_check_ints, NULL);
+        if (state) {
+            arg->state = state;
+            return 0;
+        }
+    }
+    return 1;
+}
+
+static void
+pkey_blocking_gen_stop(void *ptr)
+{
+    struct pkey_blocking_generate_arg *arg = ptr;
+    arg->interrupted = 1;
+}
+
+static void *
+pkey_blocking_gen(void *ptr)
+{
+    struct pkey_blocking_generate_arg *arg = ptr;
+
+    if (arg->genparam && EVP_PKEY_paramgen(arg->ctx, &arg->pkey) <= 0)
+        return NULL;
+    if (!arg->genparam && EVP_PKEY_keygen(arg->ctx, &arg->pkey) <= 0)
+        return NULL;
+    return arg->pkey;
+}
+
+static VALUE
+pkey_generate(int argc, VALUE *argv, VALUE self, int genparam)
+{
+    EVP_PKEY_CTX *ctx;
+    VALUE alg, options;
+    struct pkey_blocking_generate_arg gen_arg = { 0 };
+    int state;
+
+    rb_scan_args(argc, argv, "11", &alg, &options);
+    if (rb_obj_is_kind_of(alg, cPKey)) {
+        EVP_PKEY *base_pkey;
+
+        GetPKey(alg, base_pkey);
+        ctx = EVP_PKEY_CTX_new(base_pkey, NULL/* engine */);
+        if (!ctx)
+            ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    }
+    else {
+#if OSSL_OPENSSL_PREREQ(3, 0, 0)
+        ctx = EVP_PKEY_CTX_new_from_name(NULL, StringValueCStr(alg), NULL);
+        if (!ctx)
+            ossl_raise(ePKeyError, "EVP_PKEY_CTX_new_from_name");
+#else
+        const EVP_PKEY_ASN1_METHOD *ameth;
+        ENGINE *tmpeng;
+        int pkey_id;
+
+        StringValue(alg);
+        ameth = EVP_PKEY_asn1_find_str(&tmpeng, RSTRING_PTR(alg),
+                                       RSTRING_LENINT(alg));
+        if (!ameth)
+            ossl_raise(ePKeyError, "algorithm %"PRIsVALUE" not found", alg);
+        EVP_PKEY_asn1_get0_info(&pkey_id, NULL, NULL, NULL, NULL, ameth);
+#if !defined(OPENSSL_NO_ENGINE)
+        if (tmpeng)
+            ENGINE_finish(tmpeng);
+#endif
+
+        ctx = EVP_PKEY_CTX_new_id(pkey_id, NULL/* engine */);
+        if (!ctx)
+            ossl_raise(ePKeyError, "EVP_PKEY_CTX_new_id");
+#endif
+    }
+
+    if (genparam && EVP_PKEY_paramgen_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_paramgen_init");
+    }
+    if (!genparam && EVP_PKEY_keygen_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_keygen_init");
+    }
+
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(ctx, options, &state);
+        if (state) {
+            EVP_PKEY_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+
+    gen_arg.genparam = genparam;
+    gen_arg.ctx = ctx;
+    gen_arg.yield = rb_block_given_p();
+    EVP_PKEY_CTX_set_app_data(ctx, &gen_arg);
+    EVP_PKEY_CTX_set_cb(ctx, pkey_gen_cb);
+    if (gen_arg.yield)
+        pkey_blocking_gen(&gen_arg);
+    else
+        rb_thread_call_without_gvl(pkey_blocking_gen, &gen_arg,
+                                   pkey_blocking_gen_stop, &gen_arg);
+    EVP_PKEY_CTX_free(ctx);
+    if (!gen_arg.pkey) {
+        if (gen_arg.state) {
+            ossl_clear_error();
+            rb_jump_tag(gen_arg.state);
+        }
+        else {
+            ossl_raise(ePKeyError, genparam ? "EVP_PKEY_paramgen" : "EVP_PKEY_keygen");
+        }
+    }
+
+    return ossl_pkey_new(gen_arg.pkey);
+}
+
+/*
+ * call-seq:
+ *    OpenSSL::PKey.generate_parameters(algo_name [, options]) -> pkey
+ *
+ * Generates new parameters for the algorithm. _algo_name_ is a String that
+ * represents the algorithm. The optional argument _options_ is a Hash that
+ * specifies the options specific to the algorithm. The order of the options
+ * can be important.
+ *
+ * A block can be passed optionally. The meaning of the arguments passed to
+ * the block varies depending on the implementation of the algorithm. The block
+ * may be called once or multiple times, or may not even be called.
+ *
+ * For the supported options, see the documentation for the 'openssl genpkey'
+ * utility command.
+ *
+ * == Example
+ *   pkey = OpenSSL::PKey.generate_parameters("DSA", "dsa_paramgen_bits" => 2048)
+ *   p pkey.p.num_bits #=> 2048
+ */
+static VALUE
+ossl_pkey_s_generate_parameters(int argc, VALUE *argv, VALUE self)
+{
+    return pkey_generate(argc, argv, self, 1);
+}
+
+/*
+ * call-seq:
+ *    OpenSSL::PKey.generate_key(algo_name [, options]) -> pkey
+ *    OpenSSL::PKey.generate_key(pkey [, options]) -> pkey
+ *
+ * Generates a new key (pair).
+ *
+ * If a String is given as the first argument, it generates a new random key
+ * for the algorithm specified by the name just as ::generate_parameters does.
+ * If an OpenSSL::PKey::PKey is given instead, it generates a new random key
+ * for the same algorithm as the key, using the parameters the key contains.
+ *
+ * See ::generate_parameters for the details of _options_ and the given block.
+ *
+ * == Example
+ *   pkey_params = OpenSSL::PKey.generate_parameters("DSA", "dsa_paramgen_bits" => 2048)
+ *   pkey_params.priv_key #=> nil
+ *   pkey = OpenSSL::PKey.generate_key(pkey_params)
+ *   pkey.priv_key #=> #<OpenSSL::BN 6277...
+ */
+static VALUE
+ossl_pkey_s_generate_key(int argc, VALUE *argv, VALUE self)
+{
+    return pkey_generate(argc, argv, self, 0);
+}
+
+/*
+ * TODO: There is no convenient way to check the presence of public key
+ * components on OpenSSL 3.0. But since keys are immutable on 3.0, pkeys without
+ * these should only be created by OpenSSL::PKey.generate_parameters or by
+ * parsing DER-/PEM-encoded string. We would need another flag for that.
+ */
 void
 ossl_pkey_check_public_key(const EVP_PKEY *pkey)
 {
+#if OSSL_OPENSSL_PREREQ(3, 0, 0)
+    if (EVP_PKEY_missing_parameters(pkey))
+        ossl_raise(ePKeyError, "parameters missing");
+#else
     void *ptr;
     const BIGNUM *n, *e, *pubkey;
 
@@ -229,6 +546,7 @@ ossl_pkey_check_public_key(const EVP_PKEY *pkey)
 	return;
     }
     ossl_raise(ePKeyError, "public key missing");
+#endif
 }
 
 EVP_PKEY *
@@ -246,12 +564,19 @@ GetPrivPKeyPtr(VALUE obj)
 {
     EVP_PKEY *pkey;
 
-    if (rb_funcallv(obj, id_private_q, 0, NULL) != Qtrue) {
-	ossl_raise(rb_eArgError, "Private key is needed.");
-    }
     GetPKey(obj, pkey);
+    if (OSSL_PKEY_IS_PRIVATE(obj))
+        return pkey;
+    /*
+     * The EVP API does not provide a way to check if the EVP_PKEY has private
+     * components. Assuming it does...
+     */
+    if (!rb_respond_to(obj, id_private_q))
+        return pkey;
+    if (RTEST(rb_funcallv(obj, id_private_q, 0, NULL)))
+        return pkey;
 
-    return pkey;
+    rb_raise(rb_eArgError, "private key is needed");
 }
 
 EVP_PKEY *
@@ -271,16 +596,7 @@ DupPKeyPtr(VALUE obj)
 static VALUE
 ossl_pkey_alloc(VALUE klass)
 {
-    EVP_PKEY *pkey;
-    VALUE obj;
-
-    obj = NewPKey(klass);
-    if (!(pkey = EVP_PKEY_new())) {
-	ossl_raise(ePKeyError, NULL);
-    }
-    SetPKey(obj, pkey);
-
-    return obj;
+    return TypedData_Wrap_Struct(klass, &ossl_evp_pkey_type, NULL);
 }
 
 /*
@@ -299,6 +615,92 @@ ossl_pkey_initialize(VALUE self)
     return self;
 }
 
+#ifdef HAVE_EVP_PKEY_DUP
+static VALUE
+ossl_pkey_initialize_copy(VALUE self, VALUE other)
+{
+    EVP_PKEY *pkey, *pkey_other;
+
+    TypedData_Get_Struct(self, EVP_PKEY, &ossl_evp_pkey_type, pkey);
+    TypedData_Get_Struct(other, EVP_PKEY, &ossl_evp_pkey_type, pkey_other);
+    if (pkey)
+        rb_raise(rb_eTypeError, "pkey already initialized");
+    if (pkey_other) {
+        pkey = EVP_PKEY_dup(pkey_other);
+        if (!pkey)
+            ossl_raise(ePKeyError, "EVP_PKEY_dup");
+        RTYPEDDATA_DATA(self) = pkey;
+    }
+    return self;
+}
+#endif
+
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+/*
+ *  call-seq:
+ *      OpenSSL::PKey.new_raw_private_key(algo, string) -> PKey
+ *
+ * See the OpenSSL documentation for EVP_PKEY_new_raw_private_key()
+ */
+
+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);
+
+    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");
+
+    return ossl_pkey_new(pkey);
+}
+#endif
+
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+/*
+ *  call-seq:
+ *      OpenSSL::PKey.new_raw_public_key(algo, string) -> PKey
+ *
+ * See the OpenSSL documentation for EVP_PKEY_new_raw_public_key()
+ */
+
+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);
+
+    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");
+
+    return ossl_pkey_new(pkey);
+}
+#endif
+
 /*
  * call-seq:
  *    pkey.oid -> string
@@ -328,11 +730,94 @@ 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));
+    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));
+}
+
+/*
+ * call-seq:
+ *    pkey.to_text -> string
+ *
+ * Dumps key parameters, public key, and private key components contained in
+ * the key into a human-readable text.
+ *
+ * This is intended for debugging purpose.
+ *
+ * See also the man page EVP_PKEY_print_private(3).
+ */
+static VALUE
+ossl_pkey_to_text(VALUE self)
+{
+    EVP_PKEY *pkey;
+    BIO *bio;
+
+    GetPKey(self, pkey);
+    if (!(bio = BIO_new(BIO_s_mem())))
+        ossl_raise(ePKeyError, "BIO_new");
+
+    if (EVP_PKEY_print_private(bio, pkey, 0, NULL) == 1)
+        goto out;
+    OSSL_BIO_reset(bio);
+    if (EVP_PKEY_print_public(bio, pkey, 0, NULL) == 1)
+        goto out;
+    OSSL_BIO_reset(bio);
+    if (EVP_PKEY_print_params(bio, pkey, 0, NULL) == 1)
+        goto out;
+
+    BIO_free(bio);
+    ossl_raise(ePKeyError, "EVP_PKEY_print_params");
+
+  out:
+    return ossl_membio2str(bio);
+}
+
+VALUE
+ossl_pkey_export_traditional(int argc, VALUE *argv, VALUE self, int to_der)
+{
+    EVP_PKEY *pkey;
+    VALUE cipher, pass;
+    const EVP_CIPHER *enc = NULL;
+    BIO *bio;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "02", &cipher, &pass);
+    if (!NIL_P(cipher)) {
+	enc = ossl_evp_get_cipherbyname(cipher);
+	pass = ossl_pem_passwd_value(pass);
+    }
+
+    bio = BIO_new(BIO_s_mem());
+    if (!bio)
+	ossl_raise(ePKeyError, "BIO_new");
+    if (to_der) {
+	if (!i2d_PrivateKey_bio(bio, pkey)) {
+	    BIO_free(bio);
+	    ossl_raise(ePKeyError, "i2d_PrivateKey_bio");
+	}
+    }
+    else {
+#if OSSL_OPENSSL_PREREQ(1, 1, 0) || OSSL_LIBRESSL_PREREQ(3, 5, 0)
+	if (!PEM_write_bio_PrivateKey_traditional(bio, pkey, enc, NULL, 0,
+						  ossl_pem_passwd_cb,
+						  (void *)pass)) {
+#else
+	char pem_str[80];
+	const char *aname;
+
+	EVP_PKEY_asn1_get0_info(NULL, NULL, NULL, NULL, &aname, pkey->ameth);
+	snprintf(pem_str, sizeof(pem_str), "%s PRIVATE KEY", aname);
+	if (!PEM_ASN1_write_bio((i2d_of_void *)i2d_PrivateKey, pem_str, bio,
+				pkey, enc, NULL, 0, ossl_pem_passwd_cb,
+				(void *)pass)) {
+#endif
+	    BIO_free(bio);
+	    ossl_raise(ePKeyError, "PEM_write_bio_PrivateKey_traditional");
+	}
+    }
+    return ossl_membio2str(bio);
 }
 
 static VALUE
@@ -397,6 +882,18 @@ ossl_pkey_private_to_der(int argc, VALUE *argv, VALUE self)
  *
  * Serializes the private key to PEM-encoded PKCS #8 format. See #private_to_der
  * for more details.
+ *
+ * An unencrypted PEM-encoded key will look like:
+ *
+ *   -----BEGIN PRIVATE KEY-----
+ *   [...]
+ *   -----END PRIVATE KEY-----
+ *
+ * An encrypted PEM-encoded key will look like:
+ *
+ *   -----BEGIN ENCRYPTED PRIVATE KEY-----
+ *   [...]
+ *   -----END ENCRYPTED PRIVATE KEY-----
  */
 static VALUE
 ossl_pkey_private_to_pem(int argc, VALUE *argv, VALUE self)
@@ -404,8 +901,37 @@ ossl_pkey_private_to_pem(int argc, VALUE *argv, VALUE self)
     return do_pkcs8_export(argc, argv, self, 0);
 }
 
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+/*
+ *  call-seq:
+ *     pkey.raw_private_key   => string
+ *
+ *  See the OpenSSL documentation for EVP_PKEY_get_raw_private_key()
+ */
+
 static VALUE
-do_spki_export(VALUE self, int to_der)
+ossl_pkey_raw_private_key(VALUE self)
+{
+    EVP_PKEY *pkey;
+    VALUE str;
+    size_t len;
+
+    GetPKey(self, pkey);
+    if (EVP_PKEY_get_raw_private_key(pkey, NULL, &len) != 1)
+        ossl_raise(ePKeyError, "EVP_PKEY_get_raw_private_key");
+    str = rb_str_new(NULL, len);
+
+    if (EVP_PKEY_get_raw_private_key(pkey, (unsigned char *)RSTRING_PTR(str), &len) != 1)
+        ossl_raise(ePKeyError, "EVP_PKEY_get_raw_private_key");
+
+    rb_str_set_len(str, len);
+
+    return str;
+}
+#endif
+
+VALUE
+ossl_pkey_export_spki(VALUE self, int to_der)
 {
     EVP_PKEY *pkey;
     BIO *bio;
@@ -438,7 +964,7 @@ do_spki_export(VALUE self, int to_der)
 static VALUE
 ossl_pkey_public_to_der(VALUE self)
 {
-    return do_spki_export(self, 1);
+    return ossl_pkey_export_spki(self, 1);
 }
 
 /*
@@ -446,123 +972,698 @@ ossl_pkey_public_to_der(VALUE self)
  *    pkey.public_to_pem -> string
  *
  * Serializes the public key to PEM-encoded X.509 SubjectPublicKeyInfo format.
+ *
+ * A PEM-encoded key will look like:
+ *
+ *   -----BEGIN PUBLIC KEY-----
+ *   [...]
+ *   -----END PUBLIC KEY-----
  */
 static VALUE
 ossl_pkey_public_to_pem(VALUE self)
 {
-    return do_spki_export(self, 0);
+    return ossl_pkey_export_spki(self, 0);
+}
+
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+/*
+ *  call-seq:
+ *     pkey.raw_public_key   => string
+ *
+ *  See the OpenSSL documentation for EVP_PKEY_get_raw_public_key()
+ */
+
+static VALUE
+ossl_pkey_raw_public_key(VALUE self)
+{
+    EVP_PKEY *pkey;
+    VALUE str;
+    size_t len;
+
+    GetPKey(self, pkey);
+    if (EVP_PKEY_get_raw_public_key(pkey, NULL, &len) != 1)
+        ossl_raise(ePKeyError, "EVP_PKEY_get_raw_public_key");
+    str = rb_str_new(NULL, len);
+
+    if (EVP_PKEY_get_raw_public_key(pkey, (unsigned char *)RSTRING_PTR(str), &len) != 1)
+        ossl_raise(ePKeyError, "EVP_PKEY_get_raw_public_key");
+
+    rb_str_set_len(str, len);
+
+    return str;
 }
+#endif
 
 /*
  *  call-seq:
- *      pkey.sign(digest, data) -> String
+ *      pkey.compare?(another_pkey) -> true | false
  *
- * To sign the String _data_, _digest_, an instance of OpenSSL::Digest, must
- * be provided. The return value is again a String containing the signature.
- * A PKeyError is raised should errors occur.
- * Any previous state of the Digest instance is irrelevant to the signature
- * outcome, the digest instance is reset to its initial state during the
- * operation.
+ * Used primarily to check if an OpenSSL::X509::Certificate#public_key compares to its private key.
  *
  * == Example
- *   data = 'Sign me!'
- *   digest = OpenSSL::Digest.new('SHA256')
- *   pkey = OpenSSL::PKey::RSA.new(2048)
- *   signature = pkey.sign(digest, data)
+ *   x509 = OpenSSL::X509::Certificate.new(pem_encoded_certificate)
+ *   rsa_key = OpenSSL::PKey::RSA.new(pem_encoded_private_key)
+ *
+ *   rsa_key.compare?(x509.public_key) => true | false
+ */
+static VALUE
+ossl_pkey_compare(VALUE self, VALUE other)
+{
+    int ret;
+    EVP_PKEY *selfPKey;
+    EVP_PKEY *otherPKey;
+
+    GetPKey(self, selfPKey);
+    GetPKey(other, otherPKey);
+
+    /* Explicitly check the key type given EVP_PKEY_ASN1_METHOD(3)
+     * docs param_cmp could return any negative number.
+     */
+    if (EVP_PKEY_id(selfPKey) != EVP_PKEY_id(otherPKey))
+        ossl_raise(rb_eTypeError, "cannot match different PKey types");
+
+    ret = EVP_PKEY_eq(selfPKey, otherPKey);
+
+    if (ret == 0)
+        return Qfalse;
+    else if (ret == 1)
+        return Qtrue;
+    else
+        ossl_raise(ePKeyError, "EVP_PKEY_eq");
+}
+
+/*
+ * call-seq:
+ *    pkey.sign(digest, data [, options]) -> string
+ *
+ * Hashes and signs the +data+ using a message digest algorithm +digest+ and
+ * a private key +pkey+.
+ *
+ * See #verify for the verification operation.
+ *
+ * See also the man page EVP_DigestSign(3).
+ *
+ * +digest+::
+ *   A String that represents the message digest algorithm name, or +nil+
+ *   if the PKey type requires no digest algorithm.
+ *   For backwards compatibility, this can be an instance of OpenSSL::Digest.
+ *   Its state will not affect the signature.
+ * +data+::
+ *   A String. The data to be hashed and signed.
+ * +options+::
+ *   A Hash that contains algorithm specific control operations to \OpenSSL.
+ *   See OpenSSL's man page EVP_PKEY_CTX_ctrl_str(3) for details.
+ *   +options+ parameter was added in version 3.0.
+ *
+ * Example:
+ *   data = "Sign me!"
+ *   pkey = OpenSSL::PKey.generate_key("RSA", rsa_keygen_bits: 2048)
+ *   signopts = { rsa_padding_mode: "pss" }
+ *   signature = pkey.sign("SHA256", data, signopts)
+ *
+ *   # Creates a copy of the RSA key pkey, but without the private components
+ *   pub_key = pkey.public_key
+ *   puts pub_key.verify("SHA256", signature, data, signopts) # => true
  */
 static VALUE
-ossl_pkey_sign(VALUE self, VALUE digest, VALUE data)
+ossl_pkey_sign(int argc, VALUE *argv, VALUE self)
 {
     EVP_PKEY *pkey;
-    const EVP_MD *md;
+    VALUE digest, data, options, sig;
+    const EVP_MD *md = NULL;
     EVP_MD_CTX *ctx;
-    unsigned int buf_len;
-    VALUE str;
-    int result;
+    EVP_PKEY_CTX *pctx;
+    size_t siglen;
+    int state;
 
     pkey = GetPrivPKeyPtr(self);
-    md = ossl_evp_get_digestbyname(digest);
+    rb_scan_args(argc, argv, "21", &digest, &data, &options);
+    if (!NIL_P(digest))
+        md = ossl_evp_get_digestbyname(digest);
     StringValue(data);
-    str = rb_str_new(0, EVP_PKEY_size(pkey));
 
     ctx = EVP_MD_CTX_new();
     if (!ctx)
-	ossl_raise(ePKeyError, "EVP_MD_CTX_new");
-    if (!EVP_SignInit_ex(ctx, md, NULL)) {
-	EVP_MD_CTX_free(ctx);
-	ossl_raise(ePKeyError, "EVP_SignInit_ex");
+        ossl_raise(ePKeyError, "EVP_MD_CTX_new");
+    if (EVP_DigestSignInit(ctx, &pctx, md, /* engine */NULL, pkey) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestSignInit");
+    }
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(pctx, options, &state);
+        if (state) {
+            EVP_MD_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+#if OSSL_OPENSSL_PREREQ(1, 1, 1) || OSSL_LIBRESSL_PREREQ(3, 4, 0)
+    if (EVP_DigestSign(ctx, NULL, &siglen, (unsigned char *)RSTRING_PTR(data),
+                       RSTRING_LEN(data)) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestSign");
+    }
+    if (siglen > LONG_MAX) {
+        EVP_MD_CTX_free(ctx);
+        rb_raise(ePKeyError, "signature would be too large");
+    }
+    sig = ossl_str_new(NULL, (long)siglen, &state);
+    if (state) {
+        EVP_MD_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_DigestSign(ctx, (unsigned char *)RSTRING_PTR(sig), &siglen,
+                       (unsigned char *)RSTRING_PTR(data),
+                       RSTRING_LEN(data)) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestSign");
     }
-    if (!EVP_SignUpdate(ctx, RSTRING_PTR(data), RSTRING_LEN(data))) {
-	EVP_MD_CTX_free(ctx);
-	ossl_raise(ePKeyError, "EVP_SignUpdate");
+#else
+    if (EVP_DigestSignUpdate(ctx, RSTRING_PTR(data), RSTRING_LEN(data)) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestSignUpdate");
     }
-    result = EVP_SignFinal(ctx, (unsigned char *)RSTRING_PTR(str), &buf_len, pkey);
+    if (EVP_DigestSignFinal(ctx, NULL, &siglen) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestSignFinal");
+    }
+    if (siglen > LONG_MAX) {
+        EVP_MD_CTX_free(ctx);
+        rb_raise(ePKeyError, "signature would be too large");
+    }
+    sig = ossl_str_new(NULL, (long)siglen, &state);
+    if (state) {
+        EVP_MD_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_DigestSignFinal(ctx, (unsigned char *)RSTRING_PTR(sig),
+                            &siglen) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestSignFinal");
+    }
+#endif
     EVP_MD_CTX_free(ctx);
-    if (!result)
-	ossl_raise(ePKeyError, "EVP_SignFinal");
-    rb_str_set_len(str, buf_len);
-
-    return str;
+    rb_str_set_len(sig, siglen);
+    return sig;
 }
 
 /*
- *  call-seq:
- *      pkey.verify(digest, signature, data) -> String
+ * call-seq:
+ *    pkey.verify(digest, signature, data [, options]) -> true or false
  *
- * To verify the String _signature_, _digest_, an instance of
- * OpenSSL::Digest, must be provided to re-compute the message digest of the
- * original _data_, also a String. The return value is +true+ if the
- * signature is valid, +false+ otherwise. A PKeyError is raised should errors
- * occur.
- * Any previous state of the Digest instance is irrelevant to the validation
- * outcome, the digest instance is reset to its initial state during the
- * operation.
+ * Verifies the +signature+ for the +data+ using a message digest algorithm
+ * +digest+ and a public key +pkey+.
  *
- * == Example
- *   data = 'Sign me!'
- *   digest = OpenSSL::Digest.new('SHA256')
- *   pkey = OpenSSL::PKey::RSA.new(2048)
- *   signature = pkey.sign(digest, data)
- *   pub_key = pkey.public_key
- *   puts pub_key.verify(digest, signature, data) # => true
+ * Returns +true+ if the signature is successfully verified, +false+ otherwise.
+ * The caller must check the return value.
+ *
+ * See #sign for the signing operation and an example.
+ *
+ * See also the man page EVP_DigestVerify(3).
+ *
+ * +digest+::
+ *   See #sign.
+ * +signature+::
+ *   A String containing the signature to be verified.
+ * +data+::
+ *   See #sign.
+ * +options+::
+ *   See #sign. +options+ parameter was added in version 3.0.
  */
 static VALUE
-ossl_pkey_verify(VALUE self, VALUE digest, VALUE sig, VALUE data)
+ossl_pkey_verify(int argc, VALUE *argv, VALUE self)
 {
     EVP_PKEY *pkey;
-    const EVP_MD *md;
+    VALUE digest, sig, data, options;
+    const EVP_MD *md = NULL;
     EVP_MD_CTX *ctx;
-    int siglen, result;
+    EVP_PKEY_CTX *pctx;
+    int state, ret;
 
     GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "31", &digest, &sig, &data, &options);
     ossl_pkey_check_public_key(pkey);
-    md = ossl_evp_get_digestbyname(digest);
+    if (!NIL_P(digest))
+        md = ossl_evp_get_digestbyname(digest);
     StringValue(sig);
-    siglen = RSTRING_LENINT(sig);
     StringValue(data);
 
     ctx = EVP_MD_CTX_new();
     if (!ctx)
-	ossl_raise(ePKeyError, "EVP_MD_CTX_new");
-    if (!EVP_VerifyInit_ex(ctx, md, NULL)) {
-	EVP_MD_CTX_free(ctx);
-	ossl_raise(ePKeyError, "EVP_VerifyInit_ex");
+        ossl_raise(ePKeyError, "EVP_MD_CTX_new");
+    if (EVP_DigestVerifyInit(ctx, &pctx, md, /* engine */NULL, pkey) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestVerifyInit");
     }
-    if (!EVP_VerifyUpdate(ctx, RSTRING_PTR(data), RSTRING_LEN(data))) {
-	EVP_MD_CTX_free(ctx);
-	ossl_raise(ePKeyError, "EVP_VerifyUpdate");
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(pctx, options, &state);
+        if (state) {
+            EVP_MD_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+#if OSSL_OPENSSL_PREREQ(1, 1, 1) || OSSL_LIBRESSL_PREREQ(3, 4, 0)
+    ret = EVP_DigestVerify(ctx, (unsigned char *)RSTRING_PTR(sig),
+                           RSTRING_LEN(sig), (unsigned char *)RSTRING_PTR(data),
+                           RSTRING_LEN(data));
+    EVP_MD_CTX_free(ctx);
+    if (ret < 0)
+        ossl_raise(ePKeyError, "EVP_DigestVerify");
+#else
+    if (EVP_DigestVerifyUpdate(ctx, RSTRING_PTR(data), RSTRING_LEN(data)) < 1) {
+        EVP_MD_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_DigestVerifyUpdate");
     }
-    result = EVP_VerifyFinal(ctx, (unsigned char *)RSTRING_PTR(sig), siglen, pkey);
+    ret = EVP_DigestVerifyFinal(ctx, (unsigned char *)RSTRING_PTR(sig),
+                                RSTRING_LEN(sig));
     EVP_MD_CTX_free(ctx);
-    switch (result) {
-    case 0:
-	ossl_clear_error();
-	return Qfalse;
-    case 1:
-	return Qtrue;
-    default:
-	ossl_raise(ePKeyError, "EVP_VerifyFinal");
+    if (ret < 0)
+        ossl_raise(ePKeyError, "EVP_DigestVerifyFinal");
+#endif
+    if (ret)
+        return Qtrue;
+    else {
+        ossl_clear_error();
+        return Qfalse;
+    }
+}
+
+/*
+ * call-seq:
+ *    pkey.sign_raw(digest, data [, options]) -> string
+ *
+ * Signs +data+ using a private key +pkey+. Unlike #sign, +data+ will not be
+ * hashed by +digest+ automatically.
+ *
+ * See #verify_raw for the verification operation.
+ *
+ * Added in version 3.0. See also the man page EVP_PKEY_sign(3).
+ *
+ * +digest+::
+ *   A String that represents the message digest algorithm name, or +nil+
+ *   if the PKey type requires no digest algorithm.
+ *   Although this method will not hash +data+ with it, this parameter may still
+ *   be required depending on the signature algorithm.
+ * +data+::
+ *   A String. The data to be signed.
+ * +options+::
+ *   A Hash that contains algorithm specific control operations to \OpenSSL.
+ *   See OpenSSL's man page EVP_PKEY_CTX_ctrl_str(3) for details.
+ *
+ * Example:
+ *   data = "Sign me!"
+ *   hash = OpenSSL::Digest.digest("SHA256", data)
+ *   pkey = OpenSSL::PKey.generate_key("RSA", rsa_keygen_bits: 2048)
+ *   signopts = { rsa_padding_mode: "pss" }
+ *   signature = pkey.sign_raw("SHA256", hash, signopts)
+ *
+ *   # Creates a copy of the RSA key pkey, but without the private components
+ *   pub_key = pkey.public_key
+ *   puts pub_key.verify_raw("SHA256", signature, hash, signopts) # => true
+ */
+static VALUE
+ossl_pkey_sign_raw(int argc, VALUE *argv, VALUE self)
+{
+    EVP_PKEY *pkey;
+    VALUE digest, data, options, sig;
+    const EVP_MD *md = NULL;
+    EVP_PKEY_CTX *ctx;
+    size_t outlen;
+    int state;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "21", &digest, &data, &options);
+    if (!NIL_P(digest))
+        md = ossl_evp_get_digestbyname(digest);
+    StringValue(data);
+
+    ctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
+    if (!ctx)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    if (EVP_PKEY_sign_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_sign_init");
     }
+    if (md && EVP_PKEY_CTX_set_signature_md(ctx, md) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_set_signature_md");
+    }
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(ctx, options, &state);
+        if (state) {
+            EVP_PKEY_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+    if (EVP_PKEY_sign(ctx, NULL, &outlen, (unsigned char *)RSTRING_PTR(data),
+                      RSTRING_LEN(data)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_sign");
+    }
+    if (outlen > LONG_MAX) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_raise(ePKeyError, "signature would be too large");
+    }
+    sig = ossl_str_new(NULL, (long)outlen, &state);
+    if (state) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_PKEY_sign(ctx, (unsigned char *)RSTRING_PTR(sig), &outlen,
+                      (unsigned char *)RSTRING_PTR(data),
+                      RSTRING_LEN(data)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_sign");
+    }
+    EVP_PKEY_CTX_free(ctx);
+    rb_str_set_len(sig, outlen);
+    return sig;
+}
+
+/*
+ * call-seq:
+ *    pkey.verify_raw(digest, signature, data [, options]) -> true or false
+ *
+ * Verifies the +signature+ for the +data+ using a public key +pkey+. Unlike
+ * #verify, this method will not hash +data+ with +digest+ automatically.
+ *
+ * Returns +true+ if the signature is successfully verified, +false+ otherwise.
+ * The caller must check the return value.
+ *
+ * See #sign_raw for the signing operation and an example code.
+ *
+ * Added in version 3.0. See also the man page EVP_PKEY_verify(3).
+ *
+ * +signature+::
+ *   A String containing the signature to be verified.
+ */
+static VALUE
+ossl_pkey_verify_raw(int argc, VALUE *argv, VALUE self)
+{
+    EVP_PKEY *pkey;
+    VALUE digest, sig, data, options;
+    const EVP_MD *md = NULL;
+    EVP_PKEY_CTX *ctx;
+    int state, ret;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "31", &digest, &sig, &data, &options);
+    ossl_pkey_check_public_key(pkey);
+    if (!NIL_P(digest))
+        md = ossl_evp_get_digestbyname(digest);
+    StringValue(sig);
+    StringValue(data);
+
+    ctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
+    if (!ctx)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    if (EVP_PKEY_verify_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_verify_init");
+    }
+    if (md && EVP_PKEY_CTX_set_signature_md(ctx, md) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_set_signature_md");
+    }
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(ctx, options, &state);
+        if (state) {
+            EVP_PKEY_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+    ret = EVP_PKEY_verify(ctx, (unsigned char *)RSTRING_PTR(sig),
+                          RSTRING_LEN(sig),
+                          (unsigned char *)RSTRING_PTR(data),
+                          RSTRING_LEN(data));
+    EVP_PKEY_CTX_free(ctx);
+    if (ret < 0)
+        ossl_raise(ePKeyError, "EVP_PKEY_verify");
+
+    if (ret)
+        return Qtrue;
+    else {
+        ossl_clear_error();
+        return Qfalse;
+    }
+}
+
+/*
+ * call-seq:
+ *    pkey.verify_recover(digest, signature [, options]) -> string
+ *
+ * Recovers the signed data from +signature+ using a public key +pkey+. Not all
+ * signature algorithms support this operation.
+ *
+ * Added in version 3.0. See also the man page EVP_PKEY_verify_recover(3).
+ *
+ * +signature+::
+ *   A String containing the signature to be verified.
+ */
+static VALUE
+ossl_pkey_verify_recover(int argc, VALUE *argv, VALUE self)
+{
+    EVP_PKEY *pkey;
+    VALUE digest, sig, options, out;
+    const EVP_MD *md = NULL;
+    EVP_PKEY_CTX *ctx;
+    int state;
+    size_t outlen;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "21", &digest, &sig, &options);
+    ossl_pkey_check_public_key(pkey);
+    if (!NIL_P(digest))
+        md = ossl_evp_get_digestbyname(digest);
+    StringValue(sig);
+
+    ctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
+    if (!ctx)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    if (EVP_PKEY_verify_recover_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_verify_recover_init");
+    }
+    if (md && EVP_PKEY_CTX_set_signature_md(ctx, md) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_set_signature_md");
+    }
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(ctx, options, &state);
+        if (state) {
+            EVP_PKEY_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+    if (EVP_PKEY_verify_recover(ctx, NULL, &outlen,
+                                (unsigned char *)RSTRING_PTR(sig),
+                                RSTRING_LEN(sig)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_verify_recover");
+    }
+    out = ossl_str_new(NULL, (long)outlen, &state);
+    if (state) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_PKEY_verify_recover(ctx, (unsigned char *)RSTRING_PTR(out), &outlen,
+                                (unsigned char *)RSTRING_PTR(sig),
+                                RSTRING_LEN(sig)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_verify_recover");
+    }
+    EVP_PKEY_CTX_free(ctx);
+    rb_str_set_len(out, outlen);
+    return out;
+}
+
+/*
+ * call-seq:
+ *    pkey.derive(peer_pkey) -> string
+ *
+ * Derives a shared secret from _pkey_ and _peer_pkey_. _pkey_ must contain
+ * the private components, _peer_pkey_ must contain the public components.
+ */
+static VALUE
+ossl_pkey_derive(int argc, VALUE *argv, VALUE self)
+{
+    EVP_PKEY *pkey, *peer_pkey;
+    EVP_PKEY_CTX *ctx;
+    VALUE peer_pkey_obj, str;
+    size_t keylen;
+    int state;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "1", &peer_pkey_obj);
+    GetPKey(peer_pkey_obj, peer_pkey);
+
+    ctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
+    if (!ctx)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    if (EVP_PKEY_derive_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_derive_init");
+    }
+    if (EVP_PKEY_derive_set_peer(ctx, peer_pkey) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_derive_set_peer");
+    }
+    if (EVP_PKEY_derive(ctx, NULL, &keylen) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_derive");
+    }
+    if (keylen > LONG_MAX)
+        rb_raise(ePKeyError, "derived key would be too large");
+    str = ossl_str_new(NULL, (long)keylen, &state);
+    if (state) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_PKEY_derive(ctx, (unsigned char *)RSTRING_PTR(str), &keylen) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_derive");
+    }
+    EVP_PKEY_CTX_free(ctx);
+    rb_str_set_len(str, keylen);
+    return str;
+}
+
+/*
+ * call-seq:
+ *    pkey.encrypt(data [, options]) -> string
+ *
+ * Performs a public key encryption operation using +pkey+.
+ *
+ * See #decrypt for the reverse operation.
+ *
+ * Added in version 3.0. See also the man page EVP_PKEY_encrypt(3).
+ *
+ * +data+::
+ *   A String to be encrypted.
+ * +options+::
+ *   A Hash that contains algorithm specific control operations to \OpenSSL.
+ *   See OpenSSL's man page EVP_PKEY_CTX_ctrl_str(3) for details.
+ *
+ * Example:
+ *   pkey = OpenSSL::PKey.generate_key("RSA", rsa_keygen_bits: 2048)
+ *   data = "secret data"
+ *   encrypted = pkey.encrypt(data, rsa_padding_mode: "oaep")
+ *   decrypted = pkey.decrypt(data, rsa_padding_mode: "oaep")
+ *   p decrypted #=> "secret data"
+ */
+static VALUE
+ossl_pkey_encrypt(int argc, VALUE *argv, VALUE self)
+{
+    EVP_PKEY *pkey;
+    EVP_PKEY_CTX *ctx;
+    VALUE data, options, str;
+    size_t outlen;
+    int state;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "11", &data, &options);
+    StringValue(data);
+
+    ctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
+    if (!ctx)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    if (EVP_PKEY_encrypt_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_encrypt_init");
+    }
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(ctx, options, &state);
+        if (state) {
+            EVP_PKEY_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+    if (EVP_PKEY_encrypt(ctx, NULL, &outlen,
+                         (unsigned char *)RSTRING_PTR(data),
+                         RSTRING_LEN(data)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_encrypt");
+    }
+    if (outlen > LONG_MAX) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_raise(ePKeyError, "encrypted data would be too large");
+    }
+    str = ossl_str_new(NULL, (long)outlen, &state);
+    if (state) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_PKEY_encrypt(ctx, (unsigned char *)RSTRING_PTR(str), &outlen,
+                         (unsigned char *)RSTRING_PTR(data),
+                         RSTRING_LEN(data)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_encrypt");
+    }
+    EVP_PKEY_CTX_free(ctx);
+    rb_str_set_len(str, outlen);
+    return str;
+}
+
+/*
+ * call-seq:
+ *    pkey.decrypt(data [, options]) -> string
+ *
+ * Performs a public key decryption operation using +pkey+.
+ *
+ * See #encrypt for a description of the parameters and an example.
+ *
+ * Added in version 3.0. See also the man page EVP_PKEY_decrypt(3).
+ */
+static VALUE
+ossl_pkey_decrypt(int argc, VALUE *argv, VALUE self)
+{
+    EVP_PKEY *pkey;
+    EVP_PKEY_CTX *ctx;
+    VALUE data, options, str;
+    size_t outlen;
+    int state;
+
+    GetPKey(self, pkey);
+    rb_scan_args(argc, argv, "11", &data, &options);
+    StringValue(data);
+
+    ctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
+    if (!ctx)
+        ossl_raise(ePKeyError, "EVP_PKEY_CTX_new");
+    if (EVP_PKEY_decrypt_init(ctx) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_decrypt_init");
+    }
+    if (!NIL_P(options)) {
+        pkey_ctx_apply_options(ctx, options, &state);
+        if (state) {
+            EVP_PKEY_CTX_free(ctx);
+            rb_jump_tag(state);
+        }
+    }
+    if (EVP_PKEY_decrypt(ctx, NULL, &outlen,
+                         (unsigned char *)RSTRING_PTR(data),
+                         RSTRING_LEN(data)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_decrypt");
+    }
+    if (outlen > LONG_MAX) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_raise(ePKeyError, "decrypted data would be too large");
+    }
+    str = ossl_str_new(NULL, (long)outlen, &state);
+    if (state) {
+        EVP_PKEY_CTX_free(ctx);
+        rb_jump_tag(state);
+    }
+    if (EVP_PKEY_decrypt(ctx, (unsigned char *)RSTRING_PTR(str), &outlen,
+                         (unsigned char *)RSTRING_PTR(data),
+                         RSTRING_LEN(data)) <= 0) {
+        EVP_PKEY_CTX_free(ctx);
+        ossl_raise(ePKeyError, "EVP_PKEY_decrypt");
+    }
+    EVP_PKEY_CTX_free(ctx);
+    rb_str_set_len(str, outlen);
+    return str;
 }
 
 /*
@@ -648,18 +1749,41 @@ Init_ossl_pkey(void)
     cPKey = rb_define_class_under(mPKey, "PKey", rb_cObject);
 
     rb_define_module_function(mPKey, "read", ossl_pkey_new_from_data, -1);
+    rb_define_module_function(mPKey, "generate_parameters", ossl_pkey_s_generate_parameters, -1);
+    rb_define_module_function(mPKey, "generate_key", ossl_pkey_s_generate_key, -1);
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+    rb_define_module_function(mPKey, "new_raw_private_key", ossl_pkey_new_raw_private_key, 2);
+    rb_define_module_function(mPKey, "new_raw_public_key", ossl_pkey_new_raw_public_key, 2);
+#endif
 
     rb_define_alloc_func(cPKey, ossl_pkey_alloc);
     rb_define_method(cPKey, "initialize", ossl_pkey_initialize, 0);
+#ifdef HAVE_EVP_PKEY_DUP
+    rb_define_method(cPKey, "initialize_copy", ossl_pkey_initialize_copy, 1);
+#else
+    rb_undef_method(cPKey, "initialize_copy");
+#endif
     rb_define_method(cPKey, "oid", ossl_pkey_oid, 0);
     rb_define_method(cPKey, "inspect", ossl_pkey_inspect, 0);
+    rb_define_method(cPKey, "to_text", ossl_pkey_to_text, 0);
     rb_define_method(cPKey, "private_to_der", ossl_pkey_private_to_der, -1);
     rb_define_method(cPKey, "private_to_pem", ossl_pkey_private_to_pem, -1);
     rb_define_method(cPKey, "public_to_der", ossl_pkey_public_to_der, 0);
     rb_define_method(cPKey, "public_to_pem", ossl_pkey_public_to_pem, 0);
-
-    rb_define_method(cPKey, "sign", ossl_pkey_sign, 2);
-    rb_define_method(cPKey, "verify", ossl_pkey_verify, 3);
+#ifdef HAVE_EVP_PKEY_NEW_RAW_PRIVATE_KEY
+    rb_define_method(cPKey, "raw_private_key", ossl_pkey_raw_private_key, 0);
+    rb_define_method(cPKey, "raw_public_key", ossl_pkey_raw_public_key, 0);
+#endif
+    rb_define_method(cPKey, "compare?", ossl_pkey_compare, 1);
+
+    rb_define_method(cPKey, "sign", ossl_pkey_sign, -1);
+    rb_define_method(cPKey, "verify", ossl_pkey_verify, -1);
+    rb_define_method(cPKey, "sign_raw", ossl_pkey_sign_raw, -1);
+    rb_define_method(cPKey, "verify_raw", ossl_pkey_verify_raw, -1);
+    rb_define_method(cPKey, "verify_recover", ossl_pkey_verify_recover, -1);
+    rb_define_method(cPKey, "derive", ossl_pkey_derive, -1);
+    rb_define_method(cPKey, "encrypt", ossl_pkey_encrypt, -1);
+    rb_define_method(cPKey, "decrypt", ossl_pkey_decrypt, -1);
 
     id_private_q = rb_intern("private?");