diff --git a/History.md b/History.md
index a4f6bd7fd..876c37a31 100644
--- a/History.md
+++ b/History.md
@@ -1,3 +1,17 @@
+Version 3.0.2
+=============
+
+Merged changes in 2.2.3. Additionally, the following issues are fixed by this
+release.
+
+Bug fixes
+---------
+
+* Fix OpenSSL::PKey::EC#check_key not working correctly on OpenSSL 3.0.
+  [[GitHub #563]](https://github.com/ruby/openssl/issues/563)
+  [[GitHub #580]](https://github.com/ruby/openssl/pull/580)
+
+
 Version 3.0.1
 =============
 
@@ -124,6 +138,21 @@ Notable changes
     [[GitHub #342]](https://github.com/ruby/openssl/issues/342)
 
 
+Version 2.2.3
+=============
+
+Bug fixes
+---------
+
+* Fix serveral methods in OpenSSL::PKey::EC::Point attempting to raise an error
+  with an incorrect class, which would end up with a TypeError.
+  [[GitHub #570]](https://github.com/ruby/openssl/pull/570)
+* Fix OpenSSL::PKey::EC::Point#eql? and OpenSSL::PKey::EC::Group#eql?
+  incorrectly treated OpenSSL's internal errors as "not equal".
+  [[GitHub #564]](https://github.com/ruby/openssl/pull/564)
+* Fix build with LibreSSL 3.5 or later.
+
+
 Version 2.2.2
 =============
 
diff --git a/ext/openssl/ossl_pkey_ec.c b/ext/openssl/ossl_pkey_ec.c
index ab39b9c84..a59849f71 100644
--- a/ext/openssl/ossl_pkey_ec.c
+++ b/ext/openssl/ossl_pkey_ec.c
@@ -483,16 +483,28 @@ static VALUE ossl_ec_key_check_key(VALUE self)
 #ifdef HAVE_EVP_PKEY_CHECK
     EVP_PKEY *pkey;
     EVP_PKEY_CTX *pctx;
-    int ret;
+    EC_KEY *ec;
 
     GetPKey(self, pkey);
+    GetEC(self, ec);
     pctx = EVP_PKEY_CTX_new(pkey, /* engine */NULL);
     if (!pctx)
-        ossl_raise(eDHError, "EVP_PKEY_CTX_new");
-    ret = EVP_PKEY_public_check(pctx);
+        ossl_raise(eECError, "EVP_PKEY_CTX_new");
+
+    if (EC_KEY_get0_private_key(ec) != NULL) {
+        if (EVP_PKEY_check(pctx) != 1) {
+            EVP_PKEY_CTX_free(pctx);
+            ossl_raise(eECError, "EVP_PKEY_check");
+        }
+    }
+    else {
+        if (EVP_PKEY_public_check(pctx) != 1) {
+            EVP_PKEY_CTX_free(pctx);
+            ossl_raise(eECError, "EVP_PKEY_public_check");
+        }
+    }
+
     EVP_PKEY_CTX_free(pctx);
-    if (ret != 1)
-        ossl_raise(eECError, "EVP_PKEY_public_check");
 #else
     EC_KEY *ec;
 
@@ -668,10 +680,11 @@ static VALUE ossl_ec_group_eql(VALUE a, VALUE b)
     GetECGroup(a, group1);
     GetECGroup(b, group2);
 
-    if (EC_GROUP_cmp(group1, group2, ossl_bn_ctx) == 1)
-       return Qfalse;
-
-    return Qtrue;
+    switch (EC_GROUP_cmp(group1, group2, ossl_bn_ctx)) {
+    case 0: return Qtrue;
+    case 1: return Qfalse;
+    default: ossl_raise(eEC_GROUP, "EC_GROUP_cmp");
+    }
 }
 
 /*
@@ -1232,10 +1245,13 @@ static VALUE ossl_ec_point_eql(VALUE a, VALUE b)
     GetECPoint(b, point2);
     GetECGroup(group_v1, group);
 
-    if (EC_POINT_cmp(group, point1, point2, ossl_bn_ctx) == 1)
-        return Qfalse;
+    switch (EC_POINT_cmp(group, point1, point2, ossl_bn_ctx)) {
+    case 0: return Qtrue;
+    case 1: return Qfalse;
+    default: ossl_raise(eEC_POINT, "EC_POINT_cmp");
+    }
 
-    return Qtrue;
+    UNREACHABLE;
 }
 
 /*
@@ -1253,7 +1269,7 @@ static VALUE ossl_ec_point_is_at_infinity(VALUE self)
     switch (EC_POINT_is_at_infinity(group, point)) {
     case 1: return Qtrue;
     case 0: return Qfalse;
-    default: ossl_raise(cEC_POINT, "EC_POINT_is_at_infinity");
+    default: ossl_raise(eEC_POINT, "EC_POINT_is_at_infinity");
     }
 
     UNREACHABLE;
@@ -1274,7 +1290,7 @@ static VALUE ossl_ec_point_is_on_curve(VALUE self)
     switch (EC_POINT_is_on_curve(group, point, ossl_bn_ctx)) {
     case 1: return Qtrue;
     case 0: return Qfalse;
-    default: ossl_raise(cEC_POINT, "EC_POINT_is_on_curve");
+    default: ossl_raise(eEC_POINT, "EC_POINT_is_on_curve");
     }
 
     UNREACHABLE;
@@ -1297,7 +1313,7 @@ static VALUE ossl_ec_point_make_affine(VALUE self)
     rb_warn("OpenSSL::PKey::EC::Point#make_affine! is deprecated");
 #if !OSSL_OPENSSL_PREREQ(3, 0, 0)
     if (EC_POINT_make_affine(group, point, ossl_bn_ctx) != 1)
-        ossl_raise(cEC_POINT, "EC_POINT_make_affine");
+        ossl_raise(eEC_POINT, "EC_POINT_make_affine");
 #endif
 
     return self;
@@ -1316,7 +1332,7 @@ static VALUE ossl_ec_point_invert(VALUE self)
     GetECPointGroup(self, group);
 
     if (EC_POINT_invert(group, point, ossl_bn_ctx) != 1)
-        ossl_raise(cEC_POINT, "EC_POINT_invert");
+        ossl_raise(eEC_POINT, "EC_POINT_invert");
 
     return self;
 }
@@ -1334,7 +1350,7 @@ static VALUE ossl_ec_point_set_to_infinity(VALUE self)
     GetECPointGroup(self, group);
 
     if (EC_POINT_set_to_infinity(group, point) != 1)
-        ossl_raise(cEC_POINT, "EC_POINT_set_to_infinity");
+        ossl_raise(eEC_POINT, "EC_POINT_set_to_infinity");
 
     return self;
 }
diff --git a/test/openssl/fixtures/pkey/p256_too_large.pem b/test/openssl/fixtures/pkey/p256_too_large.pem
new file mode 100644
index 000000000..a73ac37f8
--- /dev/null
+++ b/test/openssl/fixtures/pkey/p256_too_large.pem
@@ -0,0 +1,5 @@
+-----BEGIN EC PRIVATE KEY-----
+MHcCAQEEIP+TT0V8Fndsnacji9tyf6hmhHywcOWTee9XkiBeJoVloAoGCCqGSM49
+AwEHoUQDQgAEBkhhJIU/2/YdPSlY2I1k25xjK4trr5OXSgXvBC21PtY0HQ7lor7A
+jzT0giJITqmcd81fwGw5+96zLcdxTF1hVQ==
+-----END EC PRIVATE KEY-----
diff --git a/test/openssl/fixtures/pkey/p384_invalid.pem b/test/openssl/fixtures/pkey/p384_invalid.pem
new file mode 100644
index 000000000..d5cdc9a3a
--- /dev/null
+++ b/test/openssl/fixtures/pkey/p384_invalid.pem
@@ -0,0 +1,6 @@
+-----BEGIN EC PRIVATE KEY-----
+MIGkAgEBBDDA1Tm0m7YhkfeVpFuarAJYVlHp2tQj+1fOBiLa10t9E8TiQO/hVfxB
+vGaVEQwOheWgBwYFK4EEACKhZANiAASyGqmryZGqdpsq5gEDIfNvgC3AwSJxiBCL
+XKHBTFRp+tCezLDOK/6V8KK/vVGBJlGFW6/I7ahyXprxS7xs7hPA9iz5YiuqXlu+
+lbrIpZOz7b73hyQQCkvbBO/Avg+hPAk=
+-----END EC PRIVATE KEY-----
diff --git a/test/openssl/test_pkey.rb b/test/openssl/test_pkey.rb
index 544340e37..1219f3f1d 100644
--- a/test/openssl/test_pkey.rb
+++ b/test/openssl/test_pkey.rb
@@ -47,6 +47,11 @@ def test_s_generate_parameters
         raise "exit!" if cb_called.size == 3
       }
     }
+    if !cb_called && openssl?(3, 0, 0) && !openssl?(3, 0, 6)
+      # Errors in BN_GENCB were not properly handled. This special pend is to
+      # suppress failures on Ubuntu 22.04, which uses OpenSSL 3.0.2.
+      pend "unstable test on OpenSSL 3.0.[0-5]"
+    end
     assert_not_empty cb_called
   end
 
diff --git a/test/openssl/test_pkey_ec.rb b/test/openssl/test_pkey_ec.rb
index 451bab032..e5fef940a 100644
--- a/test/openssl/test_pkey_ec.rb
+++ b/test/openssl/test_pkey_ec.rb
@@ -90,6 +90,13 @@ def test_check_key
     assert_equal(true, key2.public?)
     assert_equal(true, key2.check_key)
 
+    # Behavior of EVP_PKEY_public_check changes between OpenSSL 1.1.1 and 3.0
+    key4 = Fixtures.pkey("p256_too_large")
+    assert_raise(OpenSSL::PKey::ECError) { key4.check_key }
+
+    key5 = Fixtures.pkey("p384_invalid")
+    assert_raise(OpenSSL::PKey::ECError) { key5.check_key }
+
     # EC#private_key= is deprecated in 3.0 and won't work on OpenSSL 3.0
     if !openssl?(3, 0, 0)
       key2.private_key += 1