diff --git a/src/shed/_codemods.py b/src/shed/_codemods.py
index 6e0219e..09cd198 100644
--- a/src/shed/_codemods.py
+++ b/src/shed/_codemods.py
@@ -128,12 +128,7 @@ def convert_optional_literal_to_literal_none(self, _, updated_node):
         expr = updated_node.slice[0].slice.value
         args = list(expr.slice)
         args[-1] = args[-1].with_changes(comma=cst.Comma())
-        args.append(
-            cst.SubscriptElement(
-                slice=cst.Index(value=cst.Name(value="None")),
-                comma=cst.MaybeSentinel.DEFAULT,
-            )
-        )
+        args.append(cst.SubscriptElement(slice=cst.Index(value=cst.Name(value="None"))))
         expr = expr.with_changes(slice=tuple(args))
         return expr
 
@@ -305,9 +300,6 @@ def replace_unnecessary_listcomp_or_setcomp(self, _, updated_node):
     def reorder_union_literal_contents_none_last(self, _, updated_node):
         subscript_slice = list(updated_node.slice)
         subscript_slice.sort(key=lambda elt: elt.slice.value.value == "None")
-        subscript_slice[-1] = subscript_slice[-1].with_changes(
-            comma=cst.MaybeSentinel.DEFAULT
-        )
         return updated_node.with_changes(slice=subscript_slice)
 
     @m.call_if_inside(m.Annotation(annotation=m.BinaryOperation()))
@@ -332,3 +324,48 @@ def _has_none(node):
             return updated_node.with_changes(left=updated_node.right, right=node_left)
         else:
             return updated_node
+
+    @m.call_if_inside(m.Annotation(annotation=m.BinaryOperation()))
+    @m.leave(
+        m.BinaryOperation(
+            left=m.Subscript(value=m.Name(value="Literal")),
+            operator=m.BitOr(),
+            right=m.Name("None"),
+        )
+    )
+    def flatten_literal_op(self, _, updated_node):
+        literal = updated_node.left
+        args = list(literal.slice)
+        for item in args:
+            if m.matches(item, m.SubscriptElement(m.Index(m.Name("None")))):
+                return literal  # Already has "None"
+        args.append(
+            cst.SubscriptElement(
+                slice=cst.Index(value=cst.Name(value="None")),
+            )
+        )
+        return literal.with_changes(slice=tuple(args))
+
+    @m.leave(m.Subscript(value=m.Name(value="Union") | m.Name(value="Literal")))
+    def flatten_union_literal_subscript(self, _, updated_node):
+        new_slice = []
+        has_none = False
+        for item in updated_node.slice:
+            if m.matches(item.slice.value, m.Subscript(m.Name("Optional"))):
+                new_slice += item.slice.value.slice  # peel off "Optional"
+                has_none = True
+            elif m.matches(
+                item.slice.value, m.Subscript(m.Name("Union") | m.Name("Literal"))
+            ) and m.matches(updated_node.value, item.slice.value.value):
+                new_slice += item.slice.value.slice  # peel off "Union" or "Literal"
+            elif m.matches(item.slice.value, m.Name("None")):
+                has_none = True
+            else:
+                new_slice.append(item)
+        if has_none:
+            new_slice.append(
+                cst.SubscriptElement(
+                    slice=cst.Index(value=cst.Name(value="None")),
+                )
+            )
+        return updated_node.with_changes(slice=new_slice)
diff --git a/tests/recorded/flatten_literal.txt b/tests/recorded/flatten_literal.txt
new file mode 100644
index 0000000..0a41277
--- /dev/null
+++ b/tests/recorded/flatten_literal.txt
@@ -0,0 +1,15 @@
+Literal[1, 2] | None  # this should not change
+var: Literal[1, 2] | None
+var2: Literal[1, Literal[2, 3]]
+var3: Literal[None, 1, 2] | None
+Literal[1, 2, Union[bool, str]]  # this should not change
+Literal[1, 2, Union[bool, str], Optional[int]]
+
+================================================================================
+
+Literal[1, 2] | None  # this should not change
+var: Literal[1, 2, None]
+var2: Literal[1, 2, 3]
+var3: Literal[1, 2, None]
+Literal[1, 2, Union[bool, str]]  # this should not change
+Literal[1, 2, Union[bool, str], int, None]
diff --git a/tests/recorded/flatten_union.txt b/tests/recorded/flatten_union.txt
new file mode 100644
index 0000000..bd21a0e
--- /dev/null
+++ b/tests/recorded/flatten_union.txt
@@ -0,0 +1,13 @@
+Union[int, Optional[str], bool]
+Union[None, int, Optional[str]]
+Union[Union[int, float], str]
+Union[int, Literal[1, 2]]  # this should not change
+Union[int, Literal[1, 2], Optional[str]]
+
+================================================================================
+
+Union[int, str, bool, None]
+Union[int, str, None]
+Union[int, float, str]
+Union[int, Literal[1, 2]]  # this should not change
+Union[int, Literal[1, 2], str, None]