diff --git a/NEWS.md b/NEWS.md
index 9ef91778c28894..ce9345ecd8c80e 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -166,26 +166,6 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [Feature #21853]: https://bugs.ruby-lang.org/issues/21853
 [Feature #21861]: https://bugs.ruby-lang.org/issues/21861
 [Feature #21932]: https://bugs.ruby-lang.org/issues/21932
-[rbs-v3.10.1]: https://github.com/ruby/rbs/releases/tag/v3.10.1
-[rbs-v3.10.2]: https://github.com/ruby/rbs/releases/tag/v3.10.2
-[rbs-v3.10.3]: https://github.com/ruby/rbs/releases/tag/v3.10.3
-[rbs-v3.10.4]: https://github.com/ruby/rbs/releases/tag/v3.10.4
-[rbs-v4.0.0.dev.5]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.5
-[rbs-v4.0.0]: https://github.com/ruby/rbs/releases/tag/v4.0.0
-[rbs-v4.0.2]: https://github.com/ruby/rbs/releases/tag/v4.0.2
-[bigdecimal-v4.1.0]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.0
-[bigdecimal-v4.1.1]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.1
-[bigdecimal-v4.1.2]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.2
-[resolv-replace-v0.2.0]: https://github.com/ruby/resolv-replace/releases/tag/v0.2.0
-[syslog-v0.4.0]: https://github.com/ruby/syslog/releases/tag/v0.4.0
-[repl_type_completor-v0.1.13]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.13
-[repl_type_completor-v0.1.14]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.14
-[repl_type_completor-v0.1.15]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.15
-[pstore-v0.2.1]: https://github.com/ruby/pstore/releases/tag/v0.2.1
-[rdoc-v7.1.0]: https://github.com/ruby/rdoc/releases/tag/v7.1.0
-[rdoc-v7.2.0]: https://github.com/ruby/rdoc/releases/tag/v7.2.0
-[win32ole-v1.9.3]: https://github.com/ruby/win32ole/releases/tag/v1.9.3
-[irb-v1.17.0]: https://github.com/ruby/irb/releases/tag/v1.17.0
 [RubyGems-v4.0.4]: https://github.com/rubygems/rubygems/releases/tag/v4.0.4
 [RubyGems-v4.0.5]: https://github.com/rubygems/rubygems/releases/tag/v4.0.5
 [RubyGems-v4.0.6]: https://github.com/rubygems/rubygems/releases/tag/v4.0.6
@@ -223,3 +203,23 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [test-unit-3.7.6]: https://github.com/test-unit/test-unit/releases/tag/3.7.6
 [test-unit-3.7.7]: https://github.com/test-unit/test-unit/releases/tag/3.7.7
 [net-imap-v0.6.3]: https://github.com/ruby/net-imap/releases/tag/v0.6.3
+[rbs-v3.10.1]: https://github.com/ruby/rbs/releases/tag/v3.10.1
+[rbs-v3.10.2]: https://github.com/ruby/rbs/releases/tag/v3.10.2
+[rbs-v3.10.3]: https://github.com/ruby/rbs/releases/tag/v3.10.3
+[rbs-v3.10.4]: https://github.com/ruby/rbs/releases/tag/v3.10.4
+[rbs-v4.0.0.dev.5]: https://github.com/ruby/rbs/releases/tag/v4.0.0.dev.5
+[rbs-v4.0.0]: https://github.com/ruby/rbs/releases/tag/v4.0.0
+[rbs-v4.0.2]: https://github.com/ruby/rbs/releases/tag/v4.0.2
+[bigdecimal-v4.1.0]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.0
+[bigdecimal-v4.1.1]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.1
+[bigdecimal-v4.1.2]: https://github.com/ruby/bigdecimal/releases/tag/v4.1.2
+[resolv-replace-v0.2.0]: https://github.com/ruby/resolv-replace/releases/tag/v0.2.0
+[syslog-v0.4.0]: https://github.com/ruby/syslog/releases/tag/v0.4.0
+[repl_type_completor-v0.1.13]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.13
+[repl_type_completor-v0.1.14]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.14
+[repl_type_completor-v0.1.15]: https://github.com/ruby/repl_type_completor/releases/tag/v0.1.15
+[pstore-v0.2.1]: https://github.com/ruby/pstore/releases/tag/v0.2.1
+[rdoc-v7.1.0]: https://github.com/ruby/rdoc/releases/tag/v7.1.0
+[rdoc-v7.2.0]: https://github.com/ruby/rdoc/releases/tag/v7.2.0
+[win32ole-v1.9.3]: https://github.com/ruby/win32ole/releases/tag/v1.9.3
+[irb-v1.17.0]: https://github.com/ruby/irb/releases/tag/v1.17.0
diff --git a/ext/openssl/ossl_pkcs7.c b/ext/openssl/ossl_pkcs7.c
index ae0d35b7235923..79bc5d76f59247 100644
--- a/ext/openssl/ossl_pkcs7.c
+++ b/ext/openssl/ossl_pkcs7.c
@@ -1055,7 +1055,7 @@ ossl_pkcs7ri_initialize(VALUE self, VALUE cert)
 
     x509 = GetX509CertPtr(cert); /* NO NEED TO DUP */
     GetPKCS7ri(self, p7ri);
-    if (!PKCS7_RECIP_INFO_set(p7ri, x509)) {
+    if (PKCS7_RECIP_INFO_set(p7ri, x509) <= 0) {
         ossl_raise(ePKCS7Error, NULL);
     }
 
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index c6dec32a9e5e82..5a6ef726094d72 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -91,7 +91,8 @@ ossl_sslctx_s_alloc(VALUE klass)
     SSL_CTX_set_mode(ctx, mode);
     SSL_CTX_set_dh_auto(ctx, 1);
     RTYPEDDATA_DATA(obj) = ctx;
-    SSL_CTX_set_ex_data(ctx, ossl_sslctx_ex_ptr_idx, (void *)obj);
+    if (!SSL_CTX_set_ex_data(ctx, ossl_sslctx_ex_ptr_idx, (void *)obj))
+        ossl_raise(eSSLError, "SSL_CTX_set_ex_data");
 
     return obj;
 }
@@ -1672,7 +1673,8 @@ ossl_ssl_initialize(int argc, VALUE *argv, VALUE self)
         ossl_raise(eSSLError, NULL);
     RTYPEDDATA_DATA(self) = ssl;
 
-    SSL_set_ex_data(ssl, ossl_ssl_ex_ptr_idx, (void *)self);
+    if (!SSL_set_ex_data(ssl, ossl_ssl_ex_ptr_idx, (void *)self))
+        ossl_raise(eSSLError, "SSL_set_ex_data");
     SSL_set_info_callback(ssl, ssl_info_cb);
 
     rb_call_super(0, NULL);
diff --git a/ext/openssl/ossl_x509cert.c b/ext/openssl/ossl_x509cert.c
index de246759ab7af3..08dd184a0c7525 100644
--- a/ext/openssl/ossl_x509cert.c
+++ b/ext/openssl/ossl_x509cert.c
@@ -311,7 +311,9 @@ ossl_x509_set_serial(VALUE self, VALUE num)
     X509 *x509;
 
     GetX509(self, x509);
-    X509_set_serialNumber(x509, num_to_asn1integer(num, X509_get_serialNumber(x509)));
+    if (!X509_set_serialNumber(x509, num_to_asn1integer(num, X509_get_serialNumber(x509)))) {
+        ossl_raise(eX509CertError, NULL);
+    }
 
     return num;
 }
diff --git a/ext/openssl/ossl_x509name.c b/ext/openssl/ossl_x509name.c
index 2b66a4a097c29e..eb97b23c026c4f 100644
--- a/ext/openssl/ossl_x509name.c
+++ b/ext/openssl/ossl_x509name.c
@@ -366,11 +366,17 @@ static int
 ossl_x509name_cmp0(VALUE self, VALUE other)
 {
     X509_NAME *name1, *name2;
+    int result;
 
     GetX509Name(self, name1);
     GetX509Name(other, name2);
 
-    return X509_NAME_cmp(name1, name2);
+    result = X509_NAME_cmp(name1, name2);
+    if (result == -2) {
+        ossl_raise(eX509NameError, NULL);
+    }
+
+    return result;
 }
 
 /*
diff --git a/ext/openssl/ossl_x509store.c b/ext/openssl/ossl_x509store.c
index 408e18c6c418ff..9e43336c4406f2 100644
--- a/ext/openssl/ossl_x509store.c
+++ b/ext/openssl/ossl_x509store.c
@@ -190,8 +190,9 @@ ossl_x509store_set_vfy_cb(VALUE self, VALUE cb)
     X509_STORE *store;
 
     GetX509Store(self, store);
+    if (!X509_STORE_set_ex_data(store, store_ex_verify_cb_idx, (void *)cb))
+        ossl_raise(eX509StoreError, "X509_STORE_set_ex_data");
     rb_iv_set(self, "@verify_callback", cb);
-    X509_STORE_set_ex_data(store, store_ex_verify_cb_idx, (void *)cb);
     RB_OBJ_WRITTEN(self, Qundef, cb);
 
     return cb;
@@ -608,7 +609,8 @@ ossl_x509stctx_verify(VALUE self)
 
     GetX509StCtx(self, ctx);
     VALUE cb = rb_iv_get(self, "@verify_callback");
-    X509_STORE_CTX_set_ex_data(ctx, stctx_ex_verify_cb_idx, (void *)cb);
+    if (!X509_STORE_CTX_set_ex_data(ctx, stctx_ex_verify_cb_idx, (void *)cb))
+        ossl_raise(eX509StoreError, "X509_STORE_CTX_set_ex_data");
     RB_OBJ_WRITTEN(self, Qundef, cb);
 
     switch (X509_verify_cert(ctx)) {