diff --git a/python/pyspark/errors/__init__.py b/python/pyspark/errors/__init__.py
index a9bcb973a6fcf..53d5a266557f5 100644
--- a/python/pyspark/errors/__init__.py
+++ b/python/pyspark/errors/__init__.py
@@ -41,6 +41,7 @@
     PySparkRuntimeError,
     PySparkAssertionError,
     PySparkNotImplementedError,
+    PySparkPicklingError,
 )
 
 
@@ -67,4 +68,5 @@
     "PySparkRuntimeError",
     "PySparkAssertionError",
     "PySparkNotImplementedError",
+    "PySparkPicklingError",
 ]
diff --git a/python/pyspark/errors/error_classes.py b/python/pyspark/errors/error_classes.py
index 9b5d8954c20ae..ca448a169e83b 100644
--- a/python/pyspark/errors/error_classes.py
+++ b/python/pyspark/errors/error_classes.py
@@ -718,6 +718,11 @@
       "pandas iterator UDF should exhaust the input iterator."
     ]
   },
+  "STREAMING_CONNECT_SERIALIZATION_ERROR" : {
+    "message" : [
+      "Cannot serialize the function `<name>`. If you accessed the Spark session, or a DataFrame defined outside of the function, or any object that contains a Spark session, please be aware that they are not allowed in Spark Connect. For `foreachBatch`, please access the Spark session using `df.sparkSession`, where `df` is the first parameter in your `foreachBatch` function. For `StreamingQueryListener`, please access the Spark session using `self.spark`. For details please check out the PySpark doc for `foreachBatch` and `StreamingQueryListener`."
+    ]
+  },
   "TOO_MANY_VALUES" : {
     "message" : [
       "Expected <expected> values for `<item>`, got <actual>."
diff --git a/python/pyspark/errors/exceptions/base.py b/python/pyspark/errors/exceptions/base.py
index fd1c07c4df68d..1d09a68dffbfe 100644
--- a/python/pyspark/errors/exceptions/base.py
+++ b/python/pyspark/errors/exceptions/base.py
@@ -18,6 +18,7 @@
 from typing import Dict, Optional, cast
 
 from pyspark.errors.utils import ErrorClassesReader
+from pickle import PicklingError
 
 
 class PySparkException(Exception):
@@ -226,3 +227,9 @@ class PySparkNotImplementedError(PySparkException, NotImplementedError):
     """
     Wrapper class for NotImplementedError to support error classes.
     """
+
+
+class PySparkPicklingError(PySparkException, PicklingError):
+    """
+    Wrapper class for pickle.PicklingError to support error classes.
+    """
diff --git a/python/pyspark/sql/connect/plan.py b/python/pyspark/sql/connect/plan.py
index 4ef789e28a527..7952d2af99958 100644
--- a/python/pyspark/sql/connect/plan.py
+++ b/python/pyspark/sql/connect/plan.py
@@ -44,7 +44,7 @@
 from pyspark.errors import (
     PySparkTypeError,
     PySparkNotImplementedError,
-    PySparkRuntimeError,
+    PySparkPicklingError,
     IllegalArgumentException,
 )
 
@@ -2211,7 +2211,7 @@ def to_plan(self, session: "SparkConnectClient") -> proto.PythonUDTF:
         try:
             udtf.command = CloudPickleSerializer().dumps(self._func)
         except pickle.PicklingError:
-            raise PySparkRuntimeError(
+            raise PySparkPicklingError(
                 error_class="UDTF_SERIALIZATION_ERROR",
                 message_parameters={
                     "name": self._name,
diff --git a/python/pyspark/sql/connect/streaming/query.py b/python/pyspark/sql/connect/streaming/query.py
index 021d27e939de8..7cebc0e71ef1b 100644
--- a/python/pyspark/sql/connect/streaming/query.py
+++ b/python/pyspark/sql/connect/streaming/query.py
@@ -17,6 +17,7 @@
 
 import json
 import sys
+import pickle
 from typing import TYPE_CHECKING, Any, cast, Dict, List, Optional
 
 from pyspark.errors import StreamingQueryException, PySparkValueError
@@ -32,6 +33,7 @@
 from pyspark.errors.exceptions.connect import (
     StreamingQueryException as CapturedStreamingQueryException,
 )
+from pyspark.errors import PySparkPicklingError
 
 __all__ = ["StreamingQuery", "StreamingQueryManager"]
 
@@ -237,7 +239,13 @@ def addListener(self, listener: StreamingQueryListener) -> None:
         listener._init_listener_id()
         cmd = pb2.StreamingQueryManagerCommand()
         expr = proto.PythonUDF()
-        expr.command = CloudPickleSerializer().dumps(listener)
+        try:
+            expr.command = CloudPickleSerializer().dumps(listener)
+        except pickle.PicklingError:
+            raise PySparkPicklingError(
+                error_class="STREAMING_CONNECT_SERIALIZATION_ERROR",
+                message_parameters={"name": "addListener"},
+            )
         expr.python_ver = get_python_ver()
         cmd.add_listener.python_listener_payload.CopyFrom(expr)
         cmd.add_listener.id = listener._id
diff --git a/python/pyspark/sql/connect/streaming/readwriter.py b/python/pyspark/sql/connect/streaming/readwriter.py
index 89097fcf43a01..63ec7848d1eb0 100644
--- a/python/pyspark/sql/connect/streaming/readwriter.py
+++ b/python/pyspark/sql/connect/streaming/readwriter.py
@@ -20,6 +20,7 @@
 check_dependencies(__name__)
 
 import sys
+import pickle
 from typing import cast, overload, Callable, Dict, List, Optional, TYPE_CHECKING, Union
 
 from pyspark.serializers import CloudPickleSerializer
@@ -33,7 +34,7 @@
 )
 from pyspark.sql.connect.utils import get_python_ver
 from pyspark.sql.types import Row, StructType
-from pyspark.errors import PySparkTypeError, PySparkValueError
+from pyspark.errors import PySparkTypeError, PySparkValueError, PySparkPicklingError
 
 if TYPE_CHECKING:
     from pyspark.sql.connect.session import SparkSession
@@ -488,18 +489,30 @@ def foreach(self, f: Union[Callable[[Row], None], "SupportsProcess"]) -> "DataSt
         serializer = AutoBatchedSerializer(CPickleSerializer())
         command = (func, None, serializer, serializer)
         # Python ForeachWriter isn't really a PythonUDF. But we reuse it for simplicity.
-        self._write_proto.foreach_writer.python_function.command = CloudPickleSerializer().dumps(
-            command
-        )
+        try:
+            self._write_proto.foreach_writer.python_function.command = (
+                CloudPickleSerializer().dumps(command)
+            )
+        except pickle.PicklingError:
+            raise PySparkPicklingError(
+                error_class="STREAMING_CONNECT_SERIALIZATION_ERROR",
+                message_parameters={"name": "foreach"},
+            )
         self._write_proto.foreach_writer.python_function.python_ver = "%d.%d" % sys.version_info[:2]
         return self
 
     foreach.__doc__ = PySparkDataStreamWriter.foreach.__doc__
 
     def foreachBatch(self, func: Callable[["DataFrame", int], None]) -> "DataStreamWriter":
-        self._write_proto.foreach_batch.python_function.command = CloudPickleSerializer().dumps(
-            func
-        )
+        try:
+            self._write_proto.foreach_batch.python_function.command = CloudPickleSerializer().dumps(
+                func
+            )
+        except pickle.PicklingError:
+            raise PySparkPicklingError(
+                error_class="STREAMING_CONNECT_SERIALIZATION_ERROR",
+                message_parameters={"name": "foreachBatch"},
+            )
         self._write_proto.foreach_batch.python_function.python_ver = get_python_ver()
         return self
 
diff --git a/python/pyspark/sql/tests/connect/streaming/test_parity_foreachBatch.py b/python/pyspark/sql/tests/connect/streaming/test_parity_foreachBatch.py
index 01108c95391bf..0718c6a88b0da 100644
--- a/python/pyspark/sql/tests/connect/streaming/test_parity_foreachBatch.py
+++ b/python/pyspark/sql/tests/connect/streaming/test_parity_foreachBatch.py
@@ -19,6 +19,7 @@
 
 from pyspark.sql.tests.streaming.test_streaming_foreachBatch import StreamingTestsForeachBatchMixin
 from pyspark.testing.connectutils import ReusedConnectTestCase
+from pyspark.errors import PySparkPicklingError
 
 
 class StreamingForeachBatchParityTests(StreamingTestsForeachBatchMixin, ReusedConnectTestCase):
@@ -30,6 +31,35 @@ def test_streaming_foreachBatch_propagates_python_errors(self):
     def test_streaming_foreachBatch_graceful_stop(self):
         super().test_streaming_foreachBatch_graceful_stop()
 
+    # class StreamingForeachBatchParityTests(ReusedConnectTestCase):
+    def test_accessing_spark_session(self):
+        spark = self.spark
+
+        def func(df, _):
+            spark.createDataFrame([("do", "not"), ("serialize", "spark")]).collect()
+
+        error_thrown = False
+        try:
+            self.spark.readStream.format("rate").load().writeStream.foreachBatch(func).start()
+        except PySparkPicklingError as e:
+            self.assertEqual(e.getErrorClass(), "STREAMING_CONNECT_SERIALIZATION_ERROR")
+            error_thrown = True
+        self.assertTrue(error_thrown)
+
+    def test_accessing_spark_session_through_df(self):
+        dataframe = self.spark.createDataFrame([("do", "not"), ("serialize", "dataframe")])
+
+        def func(df, _):
+            dataframe.collect()
+
+        error_thrown = False
+        try:
+            self.spark.readStream.format("rate").load().writeStream.foreachBatch(func).start()
+        except PySparkPicklingError as e:
+            self.assertEqual(e.getErrorClass(), "STREAMING_CONNECT_SERIALIZATION_ERROR")
+            error_thrown = True
+        self.assertTrue(error_thrown)
+
 
 if __name__ == "__main__":
     import unittest
diff --git a/python/pyspark/sql/tests/connect/streaming/test_parity_listener.py b/python/pyspark/sql/tests/connect/streaming/test_parity_listener.py
index 5069a76cfdb73..ca02cf29ee7d1 100644
--- a/python/pyspark/sql/tests/connect/streaming/test_parity_listener.py
+++ b/python/pyspark/sql/tests/connect/streaming/test_parity_listener.py
@@ -19,6 +19,7 @@
 import time
 
 import pyspark.cloudpickle
+from pyspark.errors import PySparkPicklingError
 from pyspark.sql.tests.streaming.test_streaming_listener import StreamingListenerTestsMixin
 from pyspark.sql.streaming.listener import StreamingQueryListener
 from pyspark.sql.functions import count, lit
@@ -94,6 +95,54 @@ def test_listener_events(self):
             # Remove again to verify this won't throw any error
             self.spark.streams.removeListener(test_listener)
 
+    def test_accessing_spark_session(self):
+        spark = self.spark
+
+        class TestListener(StreamingQueryListener):
+            def onQueryStarted(self, event):
+                spark.createDataFrame([("do", "not"), ("serialize", "spark")]).collect()
+
+            def onQueryProgress(self, event):
+                pass
+
+            def onQueryIdle(self, event):
+                pass
+
+            def onQueryTerminated(self, event):
+                pass
+
+        error_thrown = False
+        try:
+            self.spark.streams.addListener(TestListener())
+        except PySparkPicklingError as e:
+            self.assertEqual(e.getErrorClass(), "STREAMING_CONNECT_SERIALIZATION_ERROR")
+            error_thrown = True
+        self.assertTrue(error_thrown)
+
+    def test_accessing_spark_session_through_df(self):
+        dataframe = self.spark.createDataFrame([("do", "not"), ("serialize", "dataframe")])
+
+        class TestListener(StreamingQueryListener):
+            def onQueryStarted(self, event):
+                dataframe.collect()
+
+            def onQueryProgress(self, event):
+                pass
+
+            def onQueryIdle(self, event):
+                pass
+
+            def onQueryTerminated(self, event):
+                pass
+
+        error_thrown = False
+        try:
+            self.spark.streams.addListener(TestListener())
+        except PySparkPicklingError as e:
+            self.assertEqual(e.getErrorClass(), "STREAMING_CONNECT_SERIALIZATION_ERROR")
+            error_thrown = True
+        self.assertTrue(error_thrown)
+
 
 if __name__ == "__main__":
     import unittest
diff --git a/python/pyspark/sql/tests/test_udtf.py b/python/pyspark/sql/tests/test_udtf.py
index 63743de5e0322..a7545c332e6a0 100644
--- a/python/pyspark/sql/tests/test_udtf.py
+++ b/python/pyspark/sql/tests/test_udtf.py
@@ -27,7 +27,7 @@
     PythonException,
     PySparkTypeError,
     AnalysisException,
-    PySparkRuntimeError,
+    PySparkPicklingError,
 )
 from pyspark.files import SparkFiles
 from pyspark.rdd import PythonEvalType
@@ -872,7 +872,7 @@ def eval(self):
                     file_obj
                     yield 1,
 
-            with self.assertRaisesRegex(PySparkRuntimeError, "UDTF_SERIALIZATION_ERROR"):
+            with self.assertRaisesRegex(PySparkPicklingError, "UDTF_SERIALIZATION_ERROR"):
                 TestUDTF().collect()
 
     def test_udtf_access_spark_session(self):
@@ -884,7 +884,7 @@ def eval(self):
                 df.collect()
                 yield 1,
 
-        with self.assertRaisesRegex(PySparkRuntimeError, "UDTF_SERIALIZATION_ERROR"):
+        with self.assertRaisesRegex(PySparkPicklingError, "UDTF_SERIALIZATION_ERROR"):
             TestUDTF().collect()
 
     def test_udtf_no_eval(self):
diff --git a/python/pyspark/sql/udtf.py b/python/pyspark/sql/udtf.py
index 833a2b9289485..0ae4a6ad40b7f 100644
--- a/python/pyspark/sql/udtf.py
+++ b/python/pyspark/sql/udtf.py
@@ -26,7 +26,7 @@
 
 from py4j.java_gateway import JavaObject
 
-from pyspark.errors import PySparkAttributeError, PySparkRuntimeError, PySparkTypeError
+from pyspark.errors import PySparkAttributeError, PySparkPicklingError, PySparkTypeError
 from pyspark.rdd import PythonEvalType
 from pyspark.sql.column import _to_java_column, _to_java_expr, _to_seq
 from pyspark.sql.pandas.utils import require_minimum_pandas_version, require_minimum_pyarrow_version
@@ -234,7 +234,7 @@ def _create_judtf(self, func: Type) -> JavaObject:
             wrapped_func = _wrap_function(sc, func)
         except pickle.PicklingError as e:
             if "CONTEXT_ONLY_VALID_ON_DRIVER" in str(e):
-                raise PySparkRuntimeError(
+                raise PySparkPicklingError(
                     error_class="UDTF_SERIALIZATION_ERROR",
                     message_parameters={
                         "name": self._name,
@@ -244,7 +244,7 @@ def _create_judtf(self, func: Type) -> JavaObject:
                         "and try again.",
                     },
                 ) from None
-            raise PySparkRuntimeError(
+            raise PySparkPicklingError(
                 error_class="UDTF_SERIALIZATION_ERROR",
                 message_parameters={
                     "name": self._name,