diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/with.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/with.py
index a9d94a2026..05249bb9ea 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/with.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/with.py
@@ -288,3 +288,22 @@ with (
 
 with (foo() as bar, baz() as bop):
     pass
+
+if True:
+    with (
+        anyio.CancelScope(shield=True)
+        if get_running_loop()
+        else contextlib.nullcontext()
+    ):
+        pass
+
+if True:
+    with (
+        anyio.CancelScope(shield=True)
+        and B and [aaaaaaaa, bbbbbbbbbbbbb, cccccccccc, dddddddddddd, eeeeeeeeeeeee]
+    ):
+        pass
+
+if True:
+    with anyio.CancelScope(shield=True) if get_running_loop() else contextlib.nullcontext():
+        pass
diff --git a/crates/ruff_python_formatter/src/other/with_item.rs b/crates/ruff_python_formatter/src/other/with_item.rs
index 0559e4a993..59a7918777 100644
--- a/crates/ruff_python_formatter/src/other/with_item.rs
+++ b/crates/ruff_python_formatter/src/other/with_item.rs
@@ -1,9 +1,12 @@
 use ruff_formatter::write;
+
 use ruff_python_ast::WithItem;
 
 use crate::comments::SourceComment;
 use crate::expression::maybe_parenthesize_expression;
-use crate::expression::parentheses::{parenthesized, Parentheses, Parenthesize};
+use crate::expression::parentheses::{
+    is_expression_parenthesized, parenthesized, Parentheses, Parenthesize,
+};
 use crate::prelude::*;
 
 #[derive(Default)]
@@ -20,12 +23,24 @@ impl FormatNodeRule<WithItem> for FormatWithItem {
         let comments = f.context().comments().clone();
         let trailing_as_comments = comments.dangling(item);
 
+        // Prefer keeping parentheses for already parenthesized expressions over
+        // parenthesizing other nodes.
+        let parenthesize = if is_expression_parenthesized(
+            context_expr.into(),
+            f.context().comments().ranges(),
+            f.context().source(),
+        ) {
+            Parenthesize::IfBreaks
+        } else {
+            Parenthesize::IfRequired
+        };
+
         write!(
             f,
             [maybe_parenthesize_expression(
                 context_expr,
                 item,
-                Parenthesize::IfRequired
+                parenthesize
             )]
         )?;
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__with.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__with.py.snap
index e49f4aaab2..0a49e0a82d 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__with.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__with.py.snap
@@ -294,6 +294,25 @@ with (
 
 with (foo() as bar, baz() as bop):
     pass
+
+if True:
+    with (
+        anyio.CancelScope(shield=True)
+        if get_running_loop()
+        else contextlib.nullcontext()
+    ):
+        pass
+
+if True:
+    with (
+        anyio.CancelScope(shield=True)
+        and B and [aaaaaaaa, bbbbbbbbbbbbb, cccccccccc, dddddddddddd, eeeeeeeeeeeee]
+    ):
+        pass
+
+if True:
+    with anyio.CancelScope(shield=True) if get_running_loop() else contextlib.nullcontext():
+        pass
 ```
 
 ## Output
@@ -580,13 +599,17 @@ with f(
 ) as b, c as d:
     pass
 
-with aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb as b:
+with (
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
+) as b:
     pass
 
 with aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb as b:
     pass
 
-with aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb as b, c as d:
+with (
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
+) as b, c as d:
     pass
 
 with (
@@ -605,6 +628,28 @@ with (
 
 with foo() as bar, baz() as bop:
     pass
+
+if True:
+    with (
+        anyio.CancelScope(shield=True)
+        if get_running_loop()
+        else contextlib.nullcontext()
+    ):
+        pass
+
+if True:
+    with (
+        anyio.CancelScope(shield=True)
+        and B
+        and [aaaaaaaa, bbbbbbbbbbbbb, cccccccccc, dddddddddddd, eeeeeeeeeeeee]
+    ):
+        pass
+
+if True:
+    with anyio.CancelScope(
+        shield=True
+    ) if get_running_loop() else contextlib.nullcontext():
+        pass
 ```