diff --git a/crates/oxc_formatter/src/formatter/comments.rs b/crates/oxc_formatter/src/formatter/comments.rs
index 6e7d8631626c3..2efd53df81760 100644
--- a/crates/oxc_formatter/src/formatter/comments.rs
+++ b/crates/oxc_formatter/src/formatter/comments.rs
@@ -451,6 +451,17 @@ impl<'a> Comments<'a> {
         )
     }
 
+    /// Checks if there is a type cast comment in the given range,
+    /// searching all comments regardless of print state.
+    pub fn has_type_cast_comment_in_range(&self, start: u32, end: u32) -> bool {
+        self.inner.iter().skip_while(|c| c.span.end < start).take_while(|c| c.span.end <= end).any(
+            |comment| {
+                self.source_text.next_non_whitespace_byte_is(comment.span.end, b'(')
+                    && self.is_type_cast_comment(comment)
+            },
+        )
+    }
+
     /// Marks the given span as a type cast node.
     pub fn mark_as_type_cast_node(&mut self, node: &impl GetSpan) {
         self.type_cast_node_span = node.span();
diff --git a/crates/oxc_formatter/src/print/call_like_expression/arguments.rs b/crates/oxc_formatter/src/print/call_like_expression/arguments.rs
index f33ea30dff9b2..2760103201d32 100644
--- a/crates/oxc_formatter/src/print/call_like_expression/arguments.rs
+++ b/crates/oxc_formatter/src/print/call_like_expression/arguments.rs
@@ -626,10 +626,24 @@ fn can_group_arrow_function_expression_argument(
         Expression::ArrowFunctionExpression(inner_arrow_function) => {
             can_group_arrow_function_expression_argument(inner_arrow_function, true, f)
         }
+        // In Prettier's Babel AST, a JSDoc type cast like `/** @type {X} */ (expr)` preserves
+        // the `ParenthesizedExpression` wrapper, so `arg.body` is not a CallExpression and
+        // `couldExpandArg` naturally returns false. In oxc's AST the parens are stripped, so we
+        // must explicitly check for type cast comments to prevent incorrect grouping.
+        // https://github.com/prettier/prettier/blob/812a4d0071270f61a7aa549d625b618be7e09d71/src/language-js/print/call-arguments.js#L232-L234
         Expression::ChainExpression(chain) => {
-            matches!(chain.expression, ChainElement::CallExpression(_)) && !is_arrow_recursion
+            matches!(chain.expression, ChainElement::CallExpression(_))
+                && !is_arrow_recursion
+                && !f
+                    .comments()
+                    .has_type_cast_comment_in_range(arrow_function.span.start, expr.span().start)
+        }
+        Expression::CallExpression(_) | Expression::ConditionalExpression(_) => {
+            !is_arrow_recursion
+                && !f
+                    .comments()
+                    .has_type_cast_comment_in_range(arrow_function.span.start, expr.span().start)
         }
-        Expression::CallExpression(_) | Expression::ConditionalExpression(_) => !is_arrow_recursion,
         _ => false,
     })
 }
diff --git a/crates/oxc_formatter/tests/fixtures/js/comments/type-cast-arrow.js b/crates/oxc_formatter/tests/fixtures/js/comments/type-cast-arrow.js
new file mode 100644
index 0000000000000..c2283c75d8aba
--- /dev/null
+++ b/crates/oxc_formatter/tests/fixtures/js/comments/type-cast-arrow.js
@@ -0,0 +1,21 @@
+items.map((child) => /** @type {SomeType} */ (visit(child)));
+
+transform_body(first_argument, second_argument, (node) => /** @type {Node} */ (context.visit(node)));
+
+// #20180 Arrow function body breaks after => when JSDoc type cast is in body
+const longer_variable = items_with_longer_name.map((child) => /** @type {SomeTypeThatIsLonger} */ (visit(child)));
+
+const body = transform_body(state.analysis.instance_body, b.id("$.run"), (node) => /** @type {Node} */ (context.visit(node)));
+
+// Edge case: very long type cast that doesn't fit even after expanding arguments
+const x = items_with_longer_name.map((child) => /** @type {SomeVeryVeryVeryVeryVeryVeryVeryLongType} */ (visit(child)));
+
+// No false positive: type cast earlier in file should not affect unrelated arrow
+const a = /** @type {X} */ (foo());
+const result = items_with_longer_name.map((child) => bar_without_typecast(child));
+
+// @satisfies type cast
+const z = items_with_longer_name.map((child) => /** @satisfies {SomeTypeThatIsLonger} */ (visit(child)));
+
+// Optional chaining with type cast
+const w = items_with_longer_name.map((child) => /** @type {SomeTypeThatIsLonger} */ (child?.visit()));
diff --git a/crates/oxc_formatter/tests/fixtures/js/comments/type-cast-arrow.js.snap b/crates/oxc_formatter/tests/fixtures/js/comments/type-cast-arrow.js.snap
new file mode 100644
index 0000000000000..7ceced9a86041
--- /dev/null
+++ b/crates/oxc_formatter/tests/fixtures/js/comments/type-cast-arrow.js.snap
@@ -0,0 +1,113 @@
+---
+source: crates/oxc_formatter/tests/fixtures/mod.rs
+---
+==================== Input ====================
+items.map((child) => /** @type {SomeType} */ (visit(child)));
+
+transform_body(first_argument, second_argument, (node) => /** @type {Node} */ (context.visit(node)));
+
+// #20180 Arrow function body breaks after => when JSDoc type cast is in body
+const longer_variable = items_with_longer_name.map((child) => /** @type {SomeTypeThatIsLonger} */ (visit(child)));
+
+const body = transform_body(state.analysis.instance_body, b.id("$.run"), (node) => /** @type {Node} */ (context.visit(node)));
+
+// Edge case: very long type cast that doesn't fit even after expanding arguments
+const x = items_with_longer_name.map((child) => /** @type {SomeVeryVeryVeryVeryVeryVeryVeryLongType} */ (visit(child)));
+
+// No false positive: type cast earlier in file should not affect unrelated arrow
+const a = /** @type {X} */ (foo());
+const result = items_with_longer_name.map((child) => bar_without_typecast(child));
+
+// @satisfies type cast
+const z = items_with_longer_name.map((child) => /** @satisfies {SomeTypeThatIsLonger} */ (visit(child)));
+
+// Optional chaining with type cast
+const w = items_with_longer_name.map((child) => /** @type {SomeTypeThatIsLonger} */ (child?.visit()));
+
+==================== Output ====================
+------------------
+{ printWidth: 80 }
+------------------
+items.map((child) => /** @type {SomeType} */ (visit(child)));
+
+transform_body(
+  first_argument,
+  second_argument,
+  (node) => /** @type {Node} */ (context.visit(node)),
+);
+
+// #20180 Arrow function body breaks after => when JSDoc type cast is in body
+const longer_variable = items_with_longer_name.map(
+  (child) => /** @type {SomeTypeThatIsLonger} */ (visit(child)),
+);
+
+const body = transform_body(
+  state.analysis.instance_body,
+  b.id("$.run"),
+  (node) => /** @type {Node} */ (context.visit(node)),
+);
+
+// Edge case: very long type cast that doesn't fit even after expanding arguments
+const x = items_with_longer_name.map(
+  (child) =>
+    /** @type {SomeVeryVeryVeryVeryVeryVeryVeryLongType} */ (visit(child)),
+);
+
+// No false positive: type cast earlier in file should not affect unrelated arrow
+const a = /** @type {X} */ (foo());
+const result = items_with_longer_name.map((child) =>
+  bar_without_typecast(child),
+);
+
+// @satisfies type cast
+const z = items_with_longer_name.map(
+  (child) => /** @satisfies {SomeTypeThatIsLonger} */ (visit(child)),
+);
+
+// Optional chaining with type cast
+const w = items_with_longer_name.map(
+  (child) => /** @type {SomeTypeThatIsLonger} */ (child?.visit()),
+);
+
+-------------------
+{ printWidth: 100 }
+-------------------
+items.map((child) => /** @type {SomeType} */ (visit(child)));
+
+transform_body(
+  first_argument,
+  second_argument,
+  (node) => /** @type {Node} */ (context.visit(node)),
+);
+
+// #20180 Arrow function body breaks after => when JSDoc type cast is in body
+const longer_variable = items_with_longer_name.map(
+  (child) => /** @type {SomeTypeThatIsLonger} */ (visit(child)),
+);
+
+const body = transform_body(
+  state.analysis.instance_body,
+  b.id("$.run"),
+  (node) => /** @type {Node} */ (context.visit(node)),
+);
+
+// Edge case: very long type cast that doesn't fit even after expanding arguments
+const x = items_with_longer_name.map(
+  (child) => /** @type {SomeVeryVeryVeryVeryVeryVeryVeryLongType} */ (visit(child)),
+);
+
+// No false positive: type cast earlier in file should not affect unrelated arrow
+const a = /** @type {X} */ (foo());
+const result = items_with_longer_name.map((child) => bar_without_typecast(child));
+
+// @satisfies type cast
+const z = items_with_longer_name.map(
+  (child) => /** @satisfies {SomeTypeThatIsLonger} */ (visit(child)),
+);
+
+// Optional chaining with type cast
+const w = items_with_longer_name.map(
+  (child) => /** @type {SomeTypeThatIsLonger} */ (child?.visit()),
+);
+
+===================== End =====================