diff --git a/bssl-compat/source/SSL_CTX_set_select_certificate_cb.cc b/bssl-compat/source/SSL_CTX_set_select_certificate_cb.cc
index f3b7e1a87e..e577cd0224 100644
--- a/bssl-compat/source/SSL_CTX_set_select_certificate_cb.cc
+++ b/bssl-compat/source/SSL_CTX_set_select_certificate_cb.cc
@@ -15,9 +15,9 @@ typedef enum ssl_select_cert_result_t (*select_certificate_cb_t)(const SSL_CLIEN
  * in_select_certificate_cb(ssl) function to query whether or not we are
  * executing within a SSL_CTX_set_select_certificate_cb() callback for that SSL
  * object, or not.
- * 
- * This mechanism is used by the SSL_get_servername() function to provide a
- * different implementation depending on it's invocation context.
+ *
+ * This mechanism is used by SSL_get_servername() & SSL_set_ocsp_response()
+ * to provide different behavior depending on invocation context.
  */
 class ActiveSelectCertificateCb {
   public:
@@ -27,14 +27,14 @@ class ActiveSelectCertificateCb {
     ~ActiveSelectCertificateCb() {
       SSL_set_ex_data(ssl_, index(), nullptr);
     }
+    static bool isActive(const SSL *ssl) {
+      return SSL_get_ex_data(ssl, index()) != nullptr;
+    }
+  private:
     static int index() {
-      static int index = SSL_get_ex_new_index(0, nullptr, nullptr, nullptr,
-                              +[](void *, void *ptr, CRYPTO_EX_DATA *, int, long, void*) {
-                                if (ptr) ossl_OPENSSL_free(ptr);
-                              });
+      static int index = SSL_get_ex_new_index(0, nullptr, nullptr, nullptr, nullptr);
       return index;
     }
-  private:
     SSL *ssl_;
 };
 
@@ -43,7 +43,7 @@ class ActiveSelectCertificateCb {
  * callback invocation for the specified SSL object.
  */
 bool in_select_certificate_cb(const SSL *ssl) {
-  return SSL_get_ex_data(ssl, ActiveSelectCertificateCb::index()) != nullptr;
+  return ActiveSelectCertificateCb::isActive(ssl);
 }
 
 
@@ -101,6 +101,12 @@ static int ssl_ctx_client_hello_cb(SSL *ssl, int *alert, void *arg) {
     return ossl_SSL_CLIENT_HELLO_ERROR;
   }
 
+  // Ensure extensions are freed even if the callback throws
+  std::unique_ptr<uint8_t, decltype(&OPENSSL_free)> cleanup(
+    const_cast<uint8_t*>(client_hello.extensions), 
+    OPENSSL_free
+  );
+
   enum ssl_select_cert_result_t result;
 
   {
@@ -108,8 +114,6 @@ static int ssl_ctx_client_hello_cb(SSL *ssl, int *alert, void *arg) {
     result = callback(&client_hello);
   }
 
-  OPENSSL_free((void*)client_hello.extensions);
-
   switch (result) {
     case ssl_select_cert_success: return ossl_SSL_CLIENT_HELLO_SUCCESS;
     case ssl_select_cert_retry:   return ossl_SSL_CLIENT_HELLO_RETRY;
diff --git a/bssl-compat/source/test/test_ssl.cc b/bssl-compat/source/test/test_ssl.cc
index 4c97a1bc01..845457b7c4 100644
--- a/bssl-compat/source/test/test_ssl.cc
+++ b/bssl-compat/source/test/test_ssl.cc
@@ -1671,6 +1671,49 @@ TEST(SSLTest, test_SSL_set_ocsp_response_leak_inside_select_certificate_cb) {
 }
 
 
+/**
+ * @brief This test exercises a leak in SSL_CTX_set_select_certificate_cb() when
+ * the certificate selection callback throws an exception.
+ *
+ * Without a fix for the leak, running this test under valgrind or similar
+ * memory checker tool will report the memory leak.
+ */
+TEST(SSLTest, test_SSL_CTX_set_select_certificate_cb_leak_from_callback_exception) {
+  TempFile server_2_key_pem        { server_2_key_pem_str };
+  TempFile server_2_cert_chain_pem { server_2_cert_chain_pem_str };
+
+  int sockets[2];
+  ASSERT_EQ(0, socketpair(AF_UNIX, SOCK_STREAM | SOCK_NONBLOCK, 0, sockets));
+  SocketCloser close[] { sockets[0], sockets[1] };
+
+  bssl::UniquePtr<SSL_CTX> server_ctx(SSL_CTX_new(TLS_server_method()));
+  bssl::UniquePtr<SSL_CTX> client_ctx(SSL_CTX_new(TLS_client_method()));
+
+  // Set up server with a select certificate callback that raises an exception
+  SSL_CTX_set_select_certificate_cb(server_ctx.get(), [](const SSL_CLIENT_HELLO *client_hello) -> ssl_select_cert_result_t {
+    throw std::runtime_error("Intentional exception to test for memory leaks");
+  });
+
+  ASSERT_TRUE(SSL_CTX_use_certificate_chain_file(server_ctx.get(), server_2_cert_chain_pem.path()));
+  ASSERT_TRUE(SSL_CTX_use_PrivateKey_file(server_ctx.get(), server_2_key_pem.path(), SSL_FILETYPE_PEM));
+  bssl::UniquePtr<SSL> server_ssl(SSL_new(server_ctx.get()));
+  ASSERT_TRUE(SSL_set_fd(server_ssl.get(), sockets[0]));
+  SSL_set_accept_state(server_ssl.get());
+
+  // Set up client
+  SSL_CTX_set_verify(client_ctx.get(), SSL_VERIFY_NONE, nullptr);
+  bssl::UniquePtr<SSL> client_ssl(SSL_new(client_ctx.get()));
+  ASSERT_TRUE(SSL_set_fd(client_ssl.get(), sockets[1]));
+  SSL_set_connect_state(client_ssl.get());
+
+  // Handshake will fail because of the exception in the callback
+  EXPECT_THROW(
+    CompleteHandshakes(client_ssl.get(), server_ssl.get()),
+    std::runtime_error
+  );
+}
+
+
 /**
  * Test that setting a TLS alert and returning ssl_verify_invalid, from a
  * callback installed via SSL_CTX_set_custom_verify(), results in a handshake