diff --git a/python/pyspark/sql/connect/session.py b/python/pyspark/sql/connect/session.py
index 6ccffc718d064..64f095a5b018b 100644
--- a/python/pyspark/sql/connect/session.py
+++ b/python/pyspark/sql/connect/session.py
@@ -26,6 +26,7 @@
 from collections.abc import Callable, Sized
 import functools
 from threading import RLock
+from types import TracebackType
 from typing import (
     Optional,
     Any,
@@ -40,6 +41,7 @@
     Mapping,
     TYPE_CHECKING,
     ClassVar,
+    Type,
 )
 
 import numpy as np
@@ -947,6 +949,57 @@ def stop(self) -> None:
                 if "SPARK_REMOTE" in os.environ:
                     del os.environ["SPARK_REMOTE"]
 
+    def __enter__(self) -> "SparkSession":
+        """
+        Enable 'with SparkSession.builder.(...).getOrCreate() as session: app' syntax.
+
+        .. versionadded:: 4.1.0
+
+        Examples
+        --------
+        >>> with SparkSession.builder.master("local").getOrCreate() as session:
+        ...     session.range(5).show()  # doctest: +SKIP
+        +---+
+        | id|
+        +---+
+        |  0|
+        |  1|
+        |  2|
+        |  3|
+        |  4|
+        +---+
+        """
+        return self
+
+    def __exit__(
+        self,
+        exc_type: Optional[Type[BaseException]],
+        exc_val: Optional[BaseException],
+        exc_tb: Optional[TracebackType],
+    ) -> None:
+        """
+        Enable 'with SparkSession.builder.(...).getOrCreate() as session: app' syntax.
+
+        Specifically stop the SparkSession on exit of the with block.
+
+        .. versionadded:: 4.1.0
+
+        Examples
+        --------
+        >>> with SparkSession.builder.master("local").getOrCreate() as session:
+        ...     session.range(5).show()  # doctest: +SKIP
+        +---+
+        | id|
+        +---+
+        |  0|
+        |  1|
+        |  2|
+        |  3|
+        |  4|
+        +---+
+        """
+        self.stop()
+
     @property
     def is_stopped(self) -> bool:
         """
diff --git a/python/pyspark/sql/tests/connect/test_connect_session.py b/python/pyspark/sql/tests/connect/test_connect_session.py
index 1857796ac9aa0..98b1dfc43dd01 100644
--- a/python/pyspark/sql/tests/connect/test_connect_session.py
+++ b/python/pyspark/sql/tests/connect/test_connect_session.py
@@ -324,6 +324,32 @@ def test_config(self):
         self.assertEqual(self.spark.conf.get("boolean"), "false")
         self.assertEqual(self.spark.conf.get("integer"), "1")
 
+    def test_context_manager_enter_exit(self):
+        """Test that SparkSession works as a context manager."""
+        # Create a new session for testing
+        with PySparkSession.builder.remote("local[2]").getOrCreate() as session:
+            self.assertIsInstance(session, RemoteSparkSession)
+            self.assertFalse(session.is_stopped)
+            
+            df = session.range(3)
+            result = df.collect()
+            self.assertEqual(len(result), 3)
+        
+        self.assertTrue(session.is_stopped)
+
+    def test_context_manager_with_exception(self):
+        """Test that SparkSession is properly stopped even when exception occurs."""
+        session = None
+        try:
+            with PySparkSession.builder.remote("local[2]").getOrCreate() as session:
+                self.assertIsInstance(session, RemoteSparkSession)
+                self.assertFalse(session.is_stopped)
+                raise ValueError("Test exception")
+        except ValueError:
+            pass  # Expected exception
+        
+        self.assertTrue(session.is_stopped)
+
 
 if __name__ == "__main__":
     from pyspark.sql.tests.connect.test_connect_session import *  # noqa: F401