diff --git a/libcst/codegen/gen_matcher_classes.py b/libcst/codegen/gen_matcher_classes.py
index b0657890d..7bb7120d3 100644
--- a/libcst/codegen/gen_matcher_classes.py
+++ b/libcst/codegen/gen_matcher_classes.py
@@ -3,6 +3,7 @@
 # This source code is licensed under the MIT license found in the
 # LICENSE file in the root directory of this source tree.
 
+import re
 from dataclasses import dataclass, fields
 from typing import Generator, List, Optional, Sequence, Set, Tuple, Type, Union
 
@@ -12,6 +13,8 @@
 
 
 CST_DIR: Set[str] = set(dir(cst))
+CLASS_RE = r"<class \'(.*?)\'>"
+OPTIONAL_RE = r"typing\.Union\[([^,]*?), NoneType]"
 
 
 class CleanseFullTypeNames(cst.CSTTransformer):
@@ -396,8 +399,8 @@ def _get_clean_type_and_aliases(
 
     # First, get the type as a parseable expression.
     typestr = repr(typeobj)
-    if typestr.startswith("<class '") and typestr.endswith("'>"):
-        typestr = typestr[8:-2]
+    typestr = re.sub(CLASS_RE, r"\1", typestr)
+    typestr = re.sub(OPTIONAL_RE, r"typing.Optional[\1]", typestr)
 
     # Now, parse the expression with LibCST.
     cleanser = CleanseFullTypeNames()
@@ -457,7 +460,7 @@ def _get_fields(node: Type[cst.CSTNode]) -> Generator[Field, None, None]:
 generated_code.append("")
 generated_code.append("# This file was generated by libcst.codegen.gen_matcher_classes")
 generated_code.append("from dataclasses import dataclass")
-generated_code.append("from typing import Callable, Sequence, Union")
+generated_code.append("from typing import Callable, Optional, Sequence, Union")
 generated_code.append("from typing_extensions import Literal")
 generated_code.append("import libcst as cst")
 generated_code.append("")
diff --git a/libcst/matchers/__init__.py b/libcst/matchers/__init__.py
index 73b3e7f26..8b7ba63f2 100644
--- a/libcst/matchers/__init__.py
+++ b/libcst/matchers/__init__.py
@@ -6,7 +6,7 @@
 
 # This file was generated by libcst.codegen.gen_matcher_classes
 from dataclasses import dataclass
-from typing import Callable, Sequence, Union
+from typing import Callable, Optional, Sequence, Union
 
 from typing_extensions import Literal
 
@@ -231,12 +231,6 @@ class And(BaseBooleanOp, BaseMatcherNode):
 AnnotationMatchType = Union[
     "Annotation", MetadataMatchType, MatchIfTrue[Callable[[cst.Annotation], bool]]
 ]
-BaseExpressionOrNoneMatchType = Union[
-    "BaseExpression",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.BaseExpression, None]], bool]],
-]
 AssignEqualMatchType = Union[
     "AssignEqual", MetadataMatchType, MatchIfTrue[Callable[[cst.AssignEqual], bool]]
 ]
@@ -260,10 +254,24 @@ class AnnAssign(BaseSmallStatement, BaseMatcherNode):
         AllOf[AnnotationMatchType],
     ] = DoNotCare()
     value: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     equal: Union[
         AssignEqualMatchType,
@@ -320,12 +328,6 @@ class Annotation(BaseMatcherNode):
     ] = DoNotCare()
 
 
-NameOrNoneMatchType = Union[
-    "Name",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Name, None]], bool]],
-]
 CommaMatchType = Union[
     "Comma", MetadataMatchType, MatchIfTrue[Callable[[cst.Comma], bool]]
 ]
@@ -340,10 +342,24 @@ class Arg(BaseMatcherNode):
         AllOf[BaseExpressionMatchType],
     ] = DoNotCare()
     keyword: Union[
-        NameOrNoneMatchType,
+        Optional["Name"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Name]], bool]],
         DoNotCareSentinel,
-        OneOf[NameOrNoneMatchType],
-        AllOf[NameOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Name"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Name]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Name"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Name]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     equal: Union[
         AssignEqualMatchType,
@@ -447,10 +463,24 @@ class Assert(BaseSmallStatement, BaseMatcherNode):
         AllOf[BaseExpressionMatchType],
     ] = DoNotCare()
     msg: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     comma: Union[
         CommaMatchType, DoNotCareSentinel, OneOf[CommaMatchType], AllOf[CommaMatchType]
@@ -2385,18 +2415,6 @@ class Comment(BaseMatcherNode):
 CompIfMatchType = Union[
     "CompIf", MetadataMatchType, MatchIfTrue[Callable[[cst.CompIf], bool]]
 ]
-CompForOrNoneMatchType = Union[
-    "CompFor",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.CompFor, None]], bool]],
-]
-AsynchronousOrNoneMatchType = Union[
-    "Asynchronous",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Asynchronous, None]], bool]],
-]
 
 
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
@@ -2494,16 +2512,44 @@ class CompFor(BaseMatcherNode):
         ],
     ] = DoNotCare()
     inner_for_in: Union[
-        CompForOrNoneMatchType,
+        Optional["CompFor"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.CompFor]], bool]],
         DoNotCareSentinel,
-        OneOf[CompForOrNoneMatchType],
-        AllOf[CompForOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["CompFor"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.CompFor]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["CompFor"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.CompFor]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     asynchronous: Union[
-        AsynchronousOrNoneMatchType,
+        Optional["Asynchronous"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
         DoNotCareSentinel,
-        OneOf[AsynchronousOrNoneMatchType],
-        AllOf[AsynchronousOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     whitespace_before: Union[
         BaseParenthesizableWhitespaceMatchType,
@@ -4126,12 +4172,6 @@ class Else(BaseMatcherNode):
 
 
 boolMatchType = Union[bool, MetadataMatchType, MatchIfTrue[Callable[[bool], bool]]]
-CommentOrNoneMatchType = Union[
-    "Comment",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Comment, None]], bool]],
-]
 NewlineMatchType = Union[
     "Newline", MetadataMatchType, MatchIfTrue[Callable[[cst.Newline], bool]]
 ]
@@ -4149,10 +4189,24 @@ class EmptyLine(BaseMatcherNode):
         AllOf[SimpleWhitespaceMatchType],
     ] = DoNotCare()
     comment: Union[
-        CommentOrNoneMatchType,
+        Optional["Comment"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Comment]], bool]],
         DoNotCareSentinel,
-        OneOf[CommentOrNoneMatchType],
-        AllOf[CommentOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Comment"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Comment]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Comment"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Comment]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     newline: Union[
         NewlineMatchType,
@@ -4190,14 +4244,6 @@ class Equal(BaseCompOp, BaseMatcherNode):
     ] = DoNotCare()
 
 
-AsNameOrNoneMatchType = Union[
-    "AsName",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.AsName, None]], bool]],
-]
-
-
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class ExceptHandler(BaseMatcherNode):
     body: Union[
@@ -4207,16 +4253,44 @@ class ExceptHandler(BaseMatcherNode):
         AllOf[BaseSuiteMatchType],
     ] = DoNotCare()
     type: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     name: Union[
-        AsNameOrNoneMatchType,
+        Optional["AsName"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
         DoNotCareSentinel,
-        OneOf[AsNameOrNoneMatchType],
-        AllOf[AsNameOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["AsName"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["AsName"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     leading_lines: Union[
         Sequence[
@@ -4659,14 +4733,6 @@ class FloorDivideAssign(BaseAugOp, BaseMatcherNode):
     ] = DoNotCare()
 
 
-ElseOrNoneMatchType = Union[
-    "Else",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Else, None]], bool]],
-]
-
-
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class For(BaseCompoundStatement, BaseStatement, BaseMatcherNode):
     target: Union[
@@ -4688,16 +4754,44 @@ class For(BaseCompoundStatement, BaseStatement, BaseMatcherNode):
         AllOf[BaseSuiteMatchType],
     ] = DoNotCare()
     orelse: Union[
-        ElseOrNoneMatchType,
+        Optional["Else"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
         DoNotCareSentinel,
-        OneOf[ElseOrNoneMatchType],
-        AllOf[ElseOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Else"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Else"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     asynchronous: Union[
-        AsynchronousOrNoneMatchType,
+        Optional["Asynchronous"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
         DoNotCareSentinel,
-        OneOf[AsynchronousOrNoneMatchType],
-        AllOf[AsynchronousOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     leading_lines: Union[
         Sequence[
@@ -5091,17 +5185,6 @@ class FormattedString(BaseExpression, BaseString, BaseMatcherNode):
     ] = DoNotCare()
 
 
-strOrNoneMatchType = Union[
-    str, None, MetadataMatchType, MatchIfTrue[Callable[[Union[str, None]], bool]]
-]
-AssignEqualOrNoneMatchType = Union[
-    "AssignEqual",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.AssignEqual, None]], bool]],
-]
-
-
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class FormattedStringExpression(BaseFormattedStringContent, BaseMatcherNode):
     expression: Union[
@@ -5111,335 +5194,47 @@ class FormattedStringExpression(BaseFormattedStringContent, BaseMatcherNode):
         AllOf[BaseExpressionMatchType],
     ] = DoNotCare()
     conversion: Union[
-        strOrNoneMatchType,
+        Optional[str],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[str]], bool]],
         DoNotCareSentinel,
-        OneOf[strOrNoneMatchType],
-        AllOf[strOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional[str],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[str]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional[str],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[str]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     format_spec: Union[
-        Union[
-            Sequence[
-                Union[
-                    BaseFormattedStringContentMatchType,
-                    DoNotCareSentinel,
-                    OneOf[BaseFormattedStringContentMatchType],
-                    AllOf[BaseFormattedStringContentMatchType],
-                    AtLeastN[
-                        Union[
-                            BaseFormattedStringContentMatchType,
-                            DoNotCareSentinel,
-                            OneOf[BaseFormattedStringContentMatchType],
-                            AllOf[BaseFormattedStringContentMatchType],
-                        ]
-                    ],
-                    AtMostN[
-                        Union[
-                            BaseFormattedStringContentMatchType,
-                            DoNotCareSentinel,
-                            OneOf[BaseFormattedStringContentMatchType],
-                            AllOf[BaseFormattedStringContentMatchType],
-                        ]
-                    ],
-                ]
-            ],
-            DoNotCareSentinel,
-            MatchIfTrue[Callable[[Sequence[cst.BaseFormattedStringContent]], bool]],
-            OneOf[
-                Union[
-                    Sequence[
-                        Union[
-                            BaseFormattedStringContentMatchType,
-                            OneOf[BaseFormattedStringContentMatchType],
-                            AllOf[BaseFormattedStringContentMatchType],
-                            AtLeastN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                            AtMostN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                        ]
-                    ],
-                    MatchIfTrue[
-                        Callable[[Sequence[cst.BaseFormattedStringContent]], bool]
-                    ],
-                ]
-            ],
-            AllOf[
-                Union[
-                    Sequence[
-                        Union[
-                            BaseFormattedStringContentMatchType,
-                            OneOf[BaseFormattedStringContentMatchType],
-                            AllOf[BaseFormattedStringContentMatchType],
-                            AtLeastN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                            AtMostN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                        ]
-                    ],
-                    MatchIfTrue[
-                        Callable[[Sequence[cst.BaseFormattedStringContent]], bool]
-                    ],
-                ]
-            ],
-        ],
-        None,
+        Optional[Sequence["BaseFormattedStringContent"]],
         MetadataMatchType,
         MatchIfTrue[
-            Callable[
-                [
-                    Union[
-                        Sequence[cst.BaseFormattedStringContent],
-                        None,
-                        OneOf[Union[Sequence[cst.BaseFormattedStringContent], None]],
-                        AllOf[Union[Sequence[cst.BaseFormattedStringContent], None]],
-                    ]
-                ],
-                bool,
-            ]
+            Callable[[Optional[Sequence[cst.BaseFormattedStringContent]]], bool]
         ],
         DoNotCareSentinel,
         OneOf[
             Union[
-                Union[
-                    Sequence[
-                        Union[
-                            BaseFormattedStringContentMatchType,
-                            OneOf[BaseFormattedStringContentMatchType],
-                            AllOf[BaseFormattedStringContentMatchType],
-                            AtLeastN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                            AtMostN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                        ]
-                    ],
-                    MatchIfTrue[
-                        Callable[[Sequence[cst.BaseFormattedStringContent]], bool]
-                    ],
-                    OneOf[
-                        Union[
-                            Sequence[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                    AtLeastN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                    AtMostN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                ]
-                            ],
-                            MatchIfTrue[
-                                Callable[
-                                    [Sequence[cst.BaseFormattedStringContent]], bool
-                                ]
-                            ],
-                        ]
-                    ],
-                    AllOf[
-                        Union[
-                            Sequence[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                    AtLeastN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                    AtMostN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                ]
-                            ],
-                            MatchIfTrue[
-                                Callable[
-                                    [Sequence[cst.BaseFormattedStringContent]], bool
-                                ]
-                            ],
-                        ]
-                    ],
-                ],
-                None,
+                Optional[Sequence["BaseFormattedStringContent"]],
                 MetadataMatchType,
                 MatchIfTrue[
-                    Callable[
-                        [
-                            Union[
-                                Sequence[cst.BaseFormattedStringContent],
-                                None,
-                                OneOf[
-                                    Union[
-                                        Sequence[cst.BaseFormattedStringContent], None
-                                    ]
-                                ],
-                                AllOf[
-                                    Union[
-                                        Sequence[cst.BaseFormattedStringContent], None
-                                    ]
-                                ],
-                            ]
-                        ],
-                        bool,
-                    ]
+                    Callable[[Optional[Sequence[cst.BaseFormattedStringContent]]], bool]
                 ],
             ]
         ],
         AllOf[
             Union[
-                Union[
-                    Sequence[
-                        Union[
-                            BaseFormattedStringContentMatchType,
-                            OneOf[BaseFormattedStringContentMatchType],
-                            AllOf[BaseFormattedStringContentMatchType],
-                            AtLeastN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                            AtMostN[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                ]
-                            ],
-                        ]
-                    ],
-                    MatchIfTrue[
-                        Callable[[Sequence[cst.BaseFormattedStringContent]], bool]
-                    ],
-                    OneOf[
-                        Union[
-                            Sequence[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                    AtLeastN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                    AtMostN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                ]
-                            ],
-                            MatchIfTrue[
-                                Callable[
-                                    [Sequence[cst.BaseFormattedStringContent]], bool
-                                ]
-                            ],
-                        ]
-                    ],
-                    AllOf[
-                        Union[
-                            Sequence[
-                                Union[
-                                    BaseFormattedStringContentMatchType,
-                                    OneOf[BaseFormattedStringContentMatchType],
-                                    AllOf[BaseFormattedStringContentMatchType],
-                                    AtLeastN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                    AtMostN[
-                                        Union[
-                                            BaseFormattedStringContentMatchType,
-                                            OneOf[BaseFormattedStringContentMatchType],
-                                            AllOf[BaseFormattedStringContentMatchType],
-                                        ]
-                                    ],
-                                ]
-                            ],
-                            MatchIfTrue[
-                                Callable[
-                                    [Sequence[cst.BaseFormattedStringContent]], bool
-                                ]
-                            ],
-                        ]
-                    ],
-                ],
-                None,
+                Optional[Sequence["BaseFormattedStringContent"]],
                 MetadataMatchType,
                 MatchIfTrue[
-                    Callable[
-                        [
-                            Union[
-                                Sequence[cst.BaseFormattedStringContent],
-                                None,
-                                OneOf[
-                                    Union[
-                                        Sequence[cst.BaseFormattedStringContent], None
-                                    ]
-                                ],
-                                AllOf[
-                                    Union[
-                                        Sequence[cst.BaseFormattedStringContent], None
-                                    ]
-                                ],
-                            ]
-                        ],
-                        bool,
-                    ]
+                    Callable[[Optional[Sequence[cst.BaseFormattedStringContent]]], bool]
                 ],
             ]
         ],
@@ -5457,10 +5252,24 @@ class FormattedStringExpression(BaseFormattedStringContent, BaseMatcherNode):
         AllOf[BaseParenthesizableWhitespaceMatchType],
     ] = DoNotCare()
     equal: Union[
-        AssignEqualOrNoneMatchType,
+        Optional["AssignEqual"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.AssignEqual]], bool]],
         DoNotCareSentinel,
-        OneOf[AssignEqualOrNoneMatchType],
-        AllOf[AssignEqualOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["AssignEqual"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AssignEqual]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["AssignEqual"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AssignEqual]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     metadata: Union[
         MetadataMatchType,
@@ -5514,12 +5323,6 @@ class From(BaseMatcherNode):
 ParametersMatchType = Union[
     "Parameters", MetadataMatchType, MatchIfTrue[Callable[[cst.Parameters], bool]]
 ]
-AnnotationOrNoneMatchType = Union[
-    "Annotation",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Annotation, None]], bool]],
-]
 
 
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
@@ -5619,17 +5422,45 @@ class FunctionDef(BaseCompoundStatement, BaseStatement, BaseMatcherNode):
             ]
         ],
     ] = DoNotCare()
-    returns: Union[
-        AnnotationOrNoneMatchType,
-        DoNotCareSentinel,
-        OneOf[AnnotationOrNoneMatchType],
-        AllOf[AnnotationOrNoneMatchType],
-    ] = DoNotCare()
+    returns: Union[
+        Optional["Annotation"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Annotation]], bool]],
+        DoNotCareSentinel,
+        OneOf[
+            Union[
+                Optional["Annotation"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Annotation]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Annotation"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Annotation]], bool]],
+            ]
+        ],
+    ] = DoNotCare()
     asynchronous: Union[
-        AsynchronousOrNoneMatchType,
+        Optional["Asynchronous"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
         DoNotCareSentinel,
-        OneOf[AsynchronousOrNoneMatchType],
-        AllOf[AsynchronousOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     leading_lines: Union[
         Sequence[
@@ -6794,10 +6625,24 @@ class ImportAlias(BaseMatcherNode):
         AllOf[AttributeOrNameMatchType],
     ] = DoNotCare()
     asname: Union[
-        AsNameOrNoneMatchType,
+        Optional["AsName"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
         DoNotCareSentinel,
-        OneOf[AsNameOrNoneMatchType],
-        AllOf[AsNameOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["AsName"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["AsName"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     comma: Union[
         CommaMatchType, DoNotCareSentinel, OneOf[CommaMatchType], AllOf[CommaMatchType]
@@ -6817,18 +6662,6 @@ class ImportAlias(BaseMatcherNode):
     MetadataMatchType,
     MatchIfTrue[Callable[[Union[cst.Attribute, cst.Name, None]], bool]],
 ]
-LeftParenOrNoneMatchType = Union[
-    "LeftParen",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.LeftParen, None]], bool]],
-]
-RightParenOrNoneMatchType = Union[
-    "RightParen",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.RightParen, None]], bool]],
-]
 
 
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
@@ -7200,16 +7033,44 @@ class ImportFrom(BaseSmallStatement, BaseMatcherNode):
         ],
     ] = DoNotCare()
     lpar: Union[
-        LeftParenOrNoneMatchType,
+        Optional["LeftParen"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.LeftParen]], bool]],
         DoNotCareSentinel,
-        OneOf[LeftParenOrNoneMatchType],
-        AllOf[LeftParenOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["LeftParen"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.LeftParen]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["LeftParen"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.LeftParen]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     rpar: Union[
-        RightParenOrNoneMatchType,
+        Optional["RightParen"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.RightParen]], bool]],
         DoNotCareSentinel,
-        OneOf[RightParenOrNoneMatchType],
-        AllOf[RightParenOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["RightParen"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.RightParen]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["RightParen"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.RightParen]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     semicolon: Union[
         SemicolonMatchType,
@@ -7369,10 +7230,24 @@ class IndentedBlock(BaseSuite, BaseMatcherNode):
         AllOf[TrailingWhitespaceMatchType],
     ] = DoNotCare()
     indent: Union[
-        strOrNoneMatchType,
+        Optional[str],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[str]], bool]],
         DoNotCareSentinel,
-        OneOf[strOrNoneMatchType],
-        AllOf[strOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional[str],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[str]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional[str],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[str]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     footer: Union[
         Sequence[
@@ -9404,10 +9279,24 @@ class NamedExpr(BaseExpression, BaseMatcherNode):
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class Newline(BaseMatcherNode):
     value: Union[
-        strOrNoneMatchType,
+        Optional[str],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[str]], bool]],
         DoNotCareSentinel,
-        OneOf[strOrNoneMatchType],
-        AllOf[strOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional[str],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[str]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional[str],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[str]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     metadata: Union[
         MetadataMatchType,
@@ -9616,10 +9505,24 @@ class Param(BaseMatcherNode):
         NameMatchType, DoNotCareSentinel, OneOf[NameMatchType], AllOf[NameMatchType]
     ] = DoNotCare()
     annotation: Union[
-        AnnotationOrNoneMatchType,
+        Optional["Annotation"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Annotation]], bool]],
         DoNotCareSentinel,
-        OneOf[AnnotationOrNoneMatchType],
-        AllOf[AnnotationOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Annotation"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Annotation]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Annotation"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Annotation]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     equal: Union[
         AssignEqualMatchType,
@@ -9628,10 +9531,24 @@ class Param(BaseMatcherNode):
         AllOf[AssignEqualMatchType],
     ] = DoNotCare()
     default: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     comma: Union[
         CommaMatchType, DoNotCareSentinel, OneOf[CommaMatchType], AllOf[CommaMatchType]
@@ -9694,12 +9611,6 @@ class ParamStar(BaseMatcherNode):
     MetadataMatchType,
     MatchIfTrue[Callable[[Union[cst.Param, cst.ParamStar]], bool]],
 ]
-ParamOrNoneMatchType = Union[
-    "Param",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Param, None]], bool]],
-]
 ParamSlashMatchType = Union[
     "ParamSlash", MetadataMatchType, MatchIfTrue[Callable[[cst.ParamSlash], bool]]
 ]
@@ -9874,10 +9785,24 @@ class Parameters(BaseMatcherNode):
         ],
     ] = DoNotCare()
     star_kwarg: Union[
-        ParamOrNoneMatchType,
+        Optional["Param"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Param]], bool]],
         DoNotCareSentinel,
-        OneOf[ParamOrNoneMatchType],
-        AllOf[ParamOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Param"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Param]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Param"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Param]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     posonly_params: Union[
         Sequence[
@@ -10154,27 +10079,47 @@ class PowerAssign(BaseAugOp, BaseMatcherNode):
     ] = DoNotCare()
 
 
-FromOrNoneMatchType = Union[
-    "From",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.From, None]], bool]],
-]
-
-
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class Raise(BaseSmallStatement, BaseMatcherNode):
     exc: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     cause: Union[
-        FromOrNoneMatchType,
+        Optional["From"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.From]], bool]],
         DoNotCareSentinel,
-        OneOf[FromOrNoneMatchType],
-        AllOf[FromOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["From"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.From]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["From"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.From]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     whitespace_after_raise: Union[
         SimpleWhitespaceMatchType,
@@ -10199,10 +10144,24 @@ class Raise(BaseSmallStatement, BaseMatcherNode):
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class Return(BaseSmallStatement, BaseMatcherNode):
     value: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     whitespace_after_return: Union[
         SimpleWhitespaceMatchType,
@@ -11268,22 +11227,64 @@ class SimpleWhitespace(BaseParenthesizableWhitespace, BaseMatcherNode):
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
 class Slice(BaseSlice, BaseMatcherNode):
     lower: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     upper: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     step: Union[
-        BaseExpressionOrNoneMatchType,
+        Optional["BaseExpression"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
         DoNotCareSentinel,
-        OneOf[BaseExpressionOrNoneMatchType],
-        AllOf[BaseExpressionOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["BaseExpression"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.BaseExpression]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     first_colon: Union[
         ColonMatchType, DoNotCareSentinel, OneOf[ColonMatchType], AllOf[ColonMatchType]
@@ -11869,10 +11870,24 @@ class TrailingWhitespace(BaseMatcherNode):
         AllOf[SimpleWhitespaceMatchType],
     ] = DoNotCare()
     comment: Union[
-        CommentOrNoneMatchType,
+        Optional["Comment"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Comment]], bool]],
         DoNotCareSentinel,
-        OneOf[CommentOrNoneMatchType],
-        AllOf[CommentOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Comment"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Comment]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Comment"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Comment]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     newline: Union[
         NewlineMatchType,
@@ -11891,12 +11906,6 @@ class TrailingWhitespace(BaseMatcherNode):
 ExceptHandlerMatchType = Union[
     "ExceptHandler", MetadataMatchType, MatchIfTrue[Callable[[cst.ExceptHandler], bool]]
 ]
-FinallyOrNoneMatchType = Union[
-    "Finally",
-    None,
-    MetadataMatchType,
-    MatchIfTrue[Callable[[Union[cst.Finally, None]], bool]],
-]
 
 
 @dataclass(frozen=True, eq=False, unsafe_hash=False)
@@ -11988,16 +11997,44 @@ class Try(BaseCompoundStatement, BaseStatement, BaseMatcherNode):
         ],
     ] = DoNotCare()
     orelse: Union[
-        ElseOrNoneMatchType,
+        Optional["Else"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
         DoNotCareSentinel,
-        OneOf[ElseOrNoneMatchType],
-        AllOf[ElseOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Else"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Else"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     finalbody: Union[
-        FinallyOrNoneMatchType,
+        Optional["Finally"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Finally]], bool]],
         DoNotCareSentinel,
-        OneOf[FinallyOrNoneMatchType],
-        AllOf[FinallyOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Finally"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Finally]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Finally"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Finally]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     leading_lines: Union[
         Sequence[
@@ -12547,10 +12584,24 @@ class While(BaseCompoundStatement, BaseStatement, BaseMatcherNode):
         AllOf[BaseSuiteMatchType],
     ] = DoNotCare()
     orelse: Union[
-        ElseOrNoneMatchType,
+        Optional["Else"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
         DoNotCareSentinel,
-        OneOf[ElseOrNoneMatchType],
-        AllOf[ElseOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Else"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Else"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Else]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     leading_lines: Union[
         Sequence[
@@ -12746,10 +12797,24 @@ class With(BaseCompoundStatement, BaseStatement, BaseMatcherNode):
         AllOf[BaseSuiteMatchType],
     ] = DoNotCare()
     asynchronous: Union[
-        AsynchronousOrNoneMatchType,
+        Optional["Asynchronous"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
         DoNotCareSentinel,
-        OneOf[AsynchronousOrNoneMatchType],
-        AllOf[AsynchronousOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["Asynchronous"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.Asynchronous]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     leading_lines: Union[
         Sequence[
@@ -12860,10 +12925,24 @@ class WithItem(BaseMatcherNode):
         AllOf[BaseExpressionMatchType],
     ] = DoNotCare()
     asname: Union[
-        AsNameOrNoneMatchType,
+        Optional["AsName"],
+        MetadataMatchType,
+        MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
         DoNotCareSentinel,
-        OneOf[AsNameOrNoneMatchType],
-        AllOf[AsNameOrNoneMatchType],
+        OneOf[
+            Union[
+                Optional["AsName"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
+            ]
+        ],
+        AllOf[
+            Union[
+                Optional["AsName"],
+                MetadataMatchType,
+                MatchIfTrue[Callable[[Optional[cst.AsName]], bool]],
+            ]
+        ],
     ] = DoNotCare()
     comma: Union[
         CommaMatchType, DoNotCareSentinel, OneOf[CommaMatchType], AllOf[CommaMatchType]