diff --git a/docs/versionhistory.rst b/docs/versionhistory.rst
index b03fcc4..7b7ec7f 100644
--- a/docs/versionhistory.rst
+++ b/docs/versionhistory.rst
@@ -7,6 +7,8 @@ This library adheres to
 **UNRELEASED**
 
 - Avoid creating reference cycles when type checking unions
+- Fixed ``Optional[...]`` being removed from the AST if it was located within a
+  subscript (`#442 <https://github.com/agronholm/typeguard/issues/442>`_)
 
 **4.1.5** (2023-09-11)
 
diff --git a/src/typeguard/_transformer.py b/src/typeguard/_transformer.py
index aeb15e3..13ac363 100644
--- a/src/typeguard/_transformer.py
+++ b/src/typeguard/_transformer.py
@@ -457,9 +457,11 @@ def visit_Subscript(self, node: Subscript) -> Any:
                 # If the transformer erased the slice entirely, just return the node
                 # value without the subscript (unless it's Optional, in which case erase
                 # the node entirely
-                if self._memo.name_matches(node.value, "typing.Optional"):
+                if self._memo.name_matches(
+                    node.value, "typing.Optional"
+                ) and not hasattr(node, "slice"):
                     return None
-                elif sys.version_info >= (3, 9) and not hasattr(node, "slice"):
+                if sys.version_info >= (3, 9) and not hasattr(node, "slice"):
                     return node.value
                 elif sys.version_info < (3, 9) and not hasattr(node.slice, "value"):
                     return node.value
diff --git a/tests/test_transformer.py b/tests/test_transformer.py
index 92ac42e..15cf9d4 100644
--- a/tests/test_transformer.py
+++ b/tests/test_transformer.py
@@ -1042,6 +1042,33 @@ def foo(x: Optional[Hashable]) -> Optional[Hashable]:
             ).strip()
         )
 
+    def test_optional_nested(self) -> None:
+        node = parse(
+            dedent(
+                """
+                from typing import Any, List, Optional
+
+                def foo(x: List[Optional[int]]) -> None:
+                    pass
+                """
+            )
+        )
+        TypeguardTransformer().visit(node)
+        assert (
+            unparse(node)
+            == dedent(
+                """
+                from typeguard import TypeCheckMemo
+                from typeguard._functions import check_argument_types
+                from typing import Any, List, Optional
+
+                def foo(x: List[Optional[int]]) -> None:
+                    memo = TypeCheckMemo(globals(), locals())
+                    check_argument_types('foo', {'x': (x, List[Optional[int]])}, memo)
+                """
+            ).strip()
+        )
+
     def test_subscript_within_union(self) -> None:
         # Regression test for #397
         node = parse(