diff --git a/crates/ruff_python_formatter/src/expression/mod.rs b/crates/ruff_python_formatter/src/expression/mod.rs
index 52255ec4f4611e..363eff9501d300 100644
--- a/crates/ruff_python_formatter/src/expression/mod.rs
+++ b/crates/ruff_python_formatter/src/expression/mod.rs
@@ -247,10 +247,13 @@ impl Format<PyFormatContext<'_>> for MaybeParenthesizeExpression<'_> {
                     if format_expression.inspect(f)?.will_break() {
                         // The group here is necessary because `format_expression` may contain IR elements
                         // that refer to the group id
-                        group(&format_expression)
-                            .with_group_id(Some(group_id))
-                            .should_expand(true)
-                            .fmt(f)
+                        group(&format_args![
+                            text("("),
+                            soft_block_indent(&format_expression),
+                            text(")")
+                        ])
+                        .with_group_id(Some(group_id))
+                        .fmt(f)
                     } else {
                         // Only add parentheses if it makes the expression fit on the line.
                         // Using the flat version as the most expanded version gives a left-to-right splitting behavior
diff --git a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__remove_await_parens.py.snap b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__remove_await_parens.py.snap
index 428ca613760819..628dbb5c6a0487 100644
--- a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__remove_await_parens.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__remove_await_parens.py.snap
@@ -93,7 +93,7 @@ async def main():
 ```diff
 --- Black
 +++ Ruff
-@@ -21,7 +21,9 @@
+@@ -21,11 +21,15 @@
  
  # Check comments
  async def main():
@@ -103,6 +103,13 @@ async def main():
 +    )
  
  
+ async def main():
+-    await asyncio.sleep(1)  # Hello
++    await (
++        asyncio.sleep(1)  # Hello
++    )
+ 
+ 
  async def main():
 ```
 
@@ -138,7 +145,9 @@ async def main():
 
 
 async def main():
-    await asyncio.sleep(1)  # Hello
+    await (
+        asyncio.sleep(1)  # Hello
+    )
 
 
 async def main():
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@parentheses__call_chains.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@parentheses__call_chains.py.snap
index 8c8c952a79d7f3..1bd2089f6b76f6 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@parentheses__call_chains.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@parentheses__call_chains.py.snap
@@ -268,7 +268,9 @@ d13 = (
 )
 
 # Doesn't fit, default
-d2 = x.e().esadjkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkfsdddd()  #
+d2 = (
+    x.e().esadjkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkfsdddd()  #
+)
 
 # Doesn't fit, fluent style
 d3 = (