diff --git a/CHANGES.md b/CHANGES.md
index e2cc70f1661..149ec8cb8c4 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -12,6 +12,8 @@
 
 - Fix formatting cells in IPython notebooks with magic methods and starting or trailing
   empty lines (#4484)
+- Stop parenthesizing context managers on Python 3.9. Python 3.10+ is unaffected.
+  (#4488)
 
 ### Preview style
 
diff --git a/src/black/mode.py b/src/black/mode.py
index 02fe1de24db..83be106e02f 100644
--- a/src/black/mode.py
+++ b/src/black/mode.py
@@ -109,7 +109,6 @@ class Feature(Enum):
         Feature.POS_ONLY_ARGUMENTS,
         Feature.UNPACKING_ON_FLOW,
         Feature.ANN_ASSIGN_EXTENDED_RHS,
-        Feature.PARENTHESIZED_CONTEXT_MANAGERS,
     },
     TargetVersion.PY310: {
         Feature.F_STRINGS,
diff --git a/tests/data/cases/python39.py b/tests/data/cases/python39.py
index 719c2b55745..56757fbea1a 100644
--- a/tests/data/cases/python39.py
+++ b/tests/data/cases/python39.py
@@ -10,6 +10,16 @@ def f():
 def f():
     ...
 
+with long_context_manager_name1(), long_context_manager_name2(), long_context_manager_name3():
+    ...
+
+with (
+    long_context_manager_name1(),
+    long_context_manager_name2(),
+    long_context_manager_name3(),
+):
+    ...
+
 # output
 
 @relaxed_decorator[0]
@@ -25,4 +35,15 @@ def f(): ...
 @extremely_long_variable_name_that_doesnt_fit := complex.expression(
     with_long="arguments_value_that_wont_fit_at_the_end_of_the_line"
 )
-def f(): ...
\ No newline at end of file
+def f(): ...
+
+
+with long_context_manager_name1(), long_context_manager_name2(), long_context_manager_name3():
+    ...
+
+with (
+    long_context_manager_name1(),
+    long_context_manager_name2(),
+    long_context_manager_name3(),
+):
+    ...