diff --git a/test/connection_query_ng.rb b/test/connection_query_ng.rb
new file mode 100644
index 0000000..b0af959
--- /dev/null
+++ b/test/connection_query_ng.rb
@@ -0,0 +1,27 @@
+# example1.rb
+require 'duckdb'
+
+temp_file = "#{File.expand_path('.', __dir__)}/data.duckdb"
+puts temp_file
+
+db = DuckDB::Database.open(temp_file)
+con = db.connect
+
+con.query('CREATE TABLE test (id INTEGER)')
+con.query('INSERT INTO test VALUES (?), (?)', 1, 2)
+
+con.close
+db.close
+
+file_last_saved1 = File.mtime(temp_file) # DBクローズ直後にファイルの最終更新日時を取得
+i = 0
+while file_last_saved1 == File.mtime(temp_file) && i < 5000
+  sleep 0.0001
+  i += 1
+end
+file_last_saved2 = File.mtime(temp_file) # しばらくしてからファイルの最終更新日時を取得
+
+# なぜか file_last_saved1 と file_last_saved2 が異なる
+p file_last_saved1 # => 2024-11-27 13:18:42.213986983 +0900 (1)
+p file_last_saved2 # => 2024-11-27 13:18:42.643766951 +0900 (2)
+File.delete(temp_file)
diff --git a/test/duckdb_test/connection_query_test.rb b/test/duckdb_test/connection_query_test.rb
new file mode 100644
index 0000000..16b5255
--- /dev/null
+++ b/test/duckdb_test/connection_query_test.rb
@@ -0,0 +1,15 @@
+# frozen_string_literal: true
+
+module DuckDBTest
+  class ConnectionQueryTest < Minitest::Test
+    def teardown
+      File.delete(@file) if File.exist?(@file)
+    end
+
+    def test_prepared_statement_destroy_in_query
+      outputs = `ruby -Ilib test/connection_query_ng.rb #{@file}`
+      @file, before, after = outputs.split("\n")
+      assert_equal(before, after)
+    end
+  end
+end