diff --git a/bindings/python/example.py b/bindings/python/example.py
index 53bfb9b34..870766e8f 100644
--- a/bindings/python/example.py
+++ b/bindings/python/example.py
@@ -1,6 +1,38 @@
 import limbo
 
-con = limbo.connect("sqlite.db")
-cur = con.cursor()
-res = cur.execute("SELECT * FROM users")
-print(res.fetchone())
+# Use the context manager to automatically close the connection
+with limbo.connect("sqlite.db") as con:
+    cur = con.cursor()
+    cur.execute("""
+            CREATE TABLE IF NOT EXISTS users (
+                id INTEGER PRIMARY KEY AUTOINCREMENT,
+                username TEXT NOT NULL,
+                email TEXT NOT NULL,
+                role TEXT NOT NULL,
+                created_at DATETIME NOT NULL DEFAULT (datetime('now'))
+            )
+        """)
+
+    # Insert some sample data
+    sample_users = [
+        ("alice", "alice@example.com", "admin"),
+        ("bob", "bob@example.com", "user"),
+        ("charlie", "charlie@example.com", "moderator"),
+        ("diana", "diana@example.com", "user"),
+    ]
+    for username, email, role in sample_users:
+        cur.execute(
+            """
+             INSERT INTO users (username, email, role)
+             VALUES (?, ?, ?)
+         """,
+            (username, email, role),
+        )
+
+    # Use commit to ensure the data is saved
+    con.commit()
+
+    # Query the table
+    res = cur.execute("SELECT * FROM users")
+    record = res.fetchone()
+    print(record)
diff --git a/bindings/python/src/lib.rs b/bindings/python/src/lib.rs
index f88666c6d..6a09e851b 100644
--- a/bindings/python/src/lib.rs
+++ b/bindings/python/src/lib.rs
@@ -193,9 +193,9 @@ impl Cursor {
     }
 
     pub fn close(&self) -> PyResult<()> {
-        Err(PyErr::new::<NotSupportedError, _>(
-            "close() is not supported in this version",
-        ))
+        self.conn.close()?;
+
+        Ok(())
     }
 
     #[pyo3(signature = (sql, parameters=None))]
@@ -244,8 +244,12 @@ impl Connection {
         })
     }
 
-    pub fn close(&self) {
-        drop(self.conn.clone());
+    pub fn close(&self) -> PyResult<()> {
+        self.conn.close().map_err(|e| {
+            PyErr::new::<OperationalError, _>(format!("Failed to close connection: {:?}", e))
+        })?;
+
+        Ok(())
     }
 
     pub fn commit(&self) -> PyResult<()> {
@@ -266,6 +270,27 @@ impl Connection {
             "Transactions are not supported in this version",
         ))
     }
+
+    fn __enter__(&self) -> PyResult<Self> {
+        Ok(self.clone())
+    }
+
+    fn __exit__(
+        &self,
+        _exc_type: Option<&Bound<'_, PyAny>>,
+        _exc_val: Option<&Bound<'_, PyAny>>,
+        _exc_tb: Option<&Bound<'_, PyAny>>,
+    ) -> PyResult<()> {
+        self.close()
+    }
+}
+
+impl Drop for Connection {
+    fn drop(&mut self) {
+        self.conn
+            .close()
+            .expect("Failed to drop (close) connection");
+    }
 }
 
 #[allow(clippy::arc_with_non_send_sync)]
diff --git a/bindings/python/tests/test_database.py b/bindings/python/tests/test_database.py
index a8276b21c..ec565a898 100644
--- a/bindings/python/tests/test_database.py
+++ b/bindings/python/tests/test_database.py
@@ -12,27 +12,41 @@ def setup_database():
     db_wal_path = "tests/database.db-wal"
 
     # Ensure the database file is created fresh for each test
-    if os.path.exists(db_path):
-        os.remove(db_path)
-    if os.path.exists(db_wal_path):
-        os.remove(db_wal_path)
+    try:
+        if os.path.exists(db_path):
+            os.remove(db_path)
+        if os.path.exists(db_wal_path):
+            os.remove(db_wal_path)
+    except PermissionError as e:
+        print(f"Failed to clean up: {e}")
 
     # Create a new database file
     conn = sqlite3.connect(db_path)
     cursor = conn.cursor()
-    cursor.execute("CREATE TABLE users (id INT PRIMARY KEY, username TEXT)")
-    cursor.execute("INSERT INTO users VALUES (1, 'alice')")
-    cursor.execute("INSERT INTO users VALUES (2, 'bob')")
+    cursor.execute("CREATE TABLE IF NOT EXISTS users (id INT PRIMARY KEY, username TEXT)")
+    cursor.execute("""
+        INSERT INTO users (id, username)
+        SELECT 1, 'alice'
+        WHERE NOT EXISTS (SELECT 1 FROM users WHERE id = 1)
+    """)
+    cursor.execute("""
+        INSERT INTO users (id, username)
+        SELECT 2, 'bob'
+        WHERE NOT EXISTS (SELECT 1 FROM users WHERE id = 2)
+    """)
     conn.commit()
     conn.close()
 
     yield db_path
 
     # Cleanup after the test
-    if os.path.exists(db_path):
-        os.remove(db_path)
-    if os.path.exists(db_wal_path):
-        os.remove(db_wal_path)
+    try:
+        if os.path.exists(db_path):
+            os.remove(db_path)
+        if os.path.exists(db_wal_path):
+            os.remove(db_wal_path)
+    except PermissionError as e:
+        print(f"Failed to clean up: {e}")
 
 
 @pytest.mark.parametrize("provider", ["sqlite3", "limbo"])
@@ -145,6 +159,18 @@ def test_commit(provider):
     assert record
 
 
+@pytest.mark.parametrize("provider", ["sqlite3", "limbo"])
+def test_with_statement(provider):
+    with connect(provider, "tests/database.db") as conn:
+        cursor = conn.cursor()
+        cursor.execute("SELECT MAX(id) FROM users")
+
+        max_id = cursor.fetchone()
+
+        assert max_id
+        assert max_id == (2,)
+
+
 def connect(provider, database):
     if provider == "limbo":
         return limbo.connect(database)