diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/if.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/if.py
index b3fc460e442f06..6aa991bb48087d 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/if.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/if.py
@@ -108,3 +108,54 @@ def something():
         if flat
         else ValuesListIterable)
     )
+
+
+# Expanding leading and trailing comments.
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = (
+    0
+    if self.thing is None
+    else before - after
+    # comment
+)
+
+before = (  # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = (
+    # comment
+    (0
+     if self.thing is None
+     else before - after
+     ))
+
+before = [
+    # comment
+    0
+    if self.thing is None
+    else before - after
+]
+
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = [
+    # comment
+    0
+    if self.thing is None
+    else before - after,
+    2
+]
diff --git a/crates/ruff_python_formatter/src/expression/expr_if_exp.rs b/crates/ruff_python_formatter/src/expression/expr_if_exp.rs
index 1b22fb568c1993..b7a38f0a40d95b 100644
--- a/crates/ruff_python_formatter/src/expression/expr_if_exp.rs
+++ b/crates/ruff_python_formatter/src/expression/expr_if_exp.rs
@@ -53,9 +53,22 @@ impl FormatNodeRule<ExprIfExp> for FormatExprIfExp {
         let comments = f.context().comments().clone();
 
         let inner = format_with(|f: &mut PyFormatter| {
-            // We place `if test` and `else orelse` on a single line, so the `test` and `orelse` leading
-            // comments go on the line before the `if` or `else` instead of directly ahead `test` or
-            // `orelse`
+            // If the expression has any leading or trailing comments, always expand it, as in:
+            // ```
+            // (
+            //     # comment
+            //     0
+            //     if self.thing is None
+            //     else before - after
+            // )
+            // ```
+            if comments.has_leading(item) || comments.has_trailing(item) {
+                expand_parent().fmt(f)?;
+            }
+
+            // We place `if test` and `else orelse` on a single line, so the `test` and `orelse`
+            // leading comments go on the line before the `if` or `else` instead of directly ahead
+            // `test` or `orelse`.
             write!(
                 f,
                 [
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__if.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__if.py.snap
index 7aa5a080c82982..7d7f8f56b85ae4 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__if.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__if.py.snap
@@ -114,6 +114,57 @@ def something():
         if flat
         else ValuesListIterable)
     )
+
+
+# Expanding leading and trailing comments.
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = (
+    0
+    if self.thing is None
+    else before - after
+    # comment
+)
+
+before = (  # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = (
+    # comment
+    (0
+     if self.thing is None
+     else before - after
+     ))
+
+before = [
+    # comment
+    0
+    if self.thing is None
+    else before - after
+]
+
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = [
+    # comment
+    0
+    if self.thing is None
+    else before - after,
+    2
+]
 ```
 
 ## Output
@@ -240,6 +291,57 @@ def something():
             else ValuesListIterable
         )
     )
+
+
+# Expanding leading and trailing comments.
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = (
+    0
+    if self.thing is None
+    else before - after
+    # comment
+)
+
+before = (  # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = [
+    # comment
+    0
+    if self.thing is None
+    else before - after
+]
+
+before = (
+    # comment
+    0
+    if self.thing is None
+    else before - after
+)
+
+before = [
+    # comment
+    0
+    if self.thing is None
+    else before - after,
+    2,
+]
 ```