diff --git a/mypy/plugins/attrs.py b/mypy/plugins/attrs.py
index 50d2955d2584..6fda965ade8b 100644
--- a/mypy/plugins/attrs.py
+++ b/mypy/plugins/attrs.py
@@ -6,6 +6,7 @@
 from typing_extensions import Final, Literal
 
 import mypy.plugin  # To avoid circular imports.
+from mypy.errorcodes import LITERAL_REQ
 from mypy.exprtotype import TypeTranslationError, expr_to_unanalyzed_type
 from mypy.nodes import (
     ARG_NAMED,
@@ -246,7 +247,11 @@ def _get_decorator_optional_bool_argument(
                     return False
                 if attr_value.fullname == "builtins.None":
                     return None
-            ctx.api.fail(f'"{name}" argument must be True or False.', ctx.reason)
+            ctx.api.fail(
+                f'"{name}" argument must be a True, False, or None literal',
+                ctx.reason,
+                code=LITERAL_REQ,
+            )
             return default
         return default
     else:
diff --git a/mypy/plugins/common.py b/mypy/plugins/common.py
index 38109892e09d..0acf3e3a6369 100644
--- a/mypy/plugins/common.py
+++ b/mypy/plugins/common.py
@@ -20,7 +20,11 @@
     Var,
 )
 from mypy.plugin import CheckerPluginInterface, ClassDefContext, SemanticAnalyzerPluginInterface
-from mypy.semanal_shared import ALLOW_INCOMPATIBLE_OVERRIDE, set_callable_name
+from mypy.semanal_shared import (
+    ALLOW_INCOMPATIBLE_OVERRIDE,
+    require_bool_literal_argument,
+    set_callable_name,
+)
 from mypy.typeops import (  # noqa: F401  # Part of public API
     try_getting_str_literals as try_getting_str_literals,
 )
@@ -54,11 +58,7 @@ def _get_bool_argument(ctx: ClassDefContext, expr: CallExpr, name: str, default:
     """
     attr_value = _get_argument(expr, name)
     if attr_value:
-        ret = ctx.api.parse_bool(attr_value)
-        if ret is None:
-            ctx.api.fail(f'"{name}" argument must be True or False.', expr)
-            return default
-        return ret
+        return require_bool_literal_argument(ctx.api, attr_value, name, default)
     return default
 
 
diff --git a/mypy/plugins/dataclasses.py b/mypy/plugins/dataclasses.py
index 3feb644dc8ea..872765847073 100644
--- a/mypy/plugins/dataclasses.py
+++ b/mypy/plugins/dataclasses.py
@@ -41,7 +41,7 @@
     add_method_to_class,
     deserialize_and_fixup_type,
 )
-from mypy.semanal_shared import find_dataclass_transform_spec
+from mypy.semanal_shared import find_dataclass_transform_spec, require_bool_literal_argument
 from mypy.server.trigger import make_wildcard_trigger
 from mypy.state import state
 from mypy.typeops import map_type_from_supertype
@@ -678,11 +678,7 @@ def _get_bool_arg(self, name: str, default: bool) -> bool:
         # class's keyword arguments (ie `class Subclass(Parent, kwarg1=..., kwarg2=...)`)
         expression = self._cls.keywords.get(name)
         if expression is not None:
-            value = self._api.parse_bool(self._cls.keywords[name])
-            if value is not None:
-                return value
-            else:
-                self._api.fail(f'"{name}" argument must be True or False', expression)
+            return require_bool_literal_argument(self._api, expression, name, default)
         return default
 
 
diff --git a/mypy/semanal.py b/mypy/semanal.py
index 8dcea36f41b9..8c16b0addd45 100644
--- a/mypy/semanal.py
+++ b/mypy/semanal.py
@@ -216,6 +216,7 @@
     calculate_tuple_fallback,
     find_dataclass_transform_spec,
     has_placeholder,
+    require_bool_literal_argument,
     set_callable_name as set_callable_name,
 )
 from mypy.semanal_typeddict import TypedDictAnalyzer
@@ -6473,15 +6474,19 @@ def parse_dataclass_transform_spec(self, call: CallExpr) -> DataclassTransformSp
         typing.dataclass_transform."""
         parameters = DataclassTransformSpec()
         for name, value in zip(call.arg_names, call.args):
+            # Skip any positional args. Note that any such args are invalid, but we can rely on
+            # typeshed to enforce this and don't need an additional error here.
+            if name is None:
+                continue
+
             # field_specifiers is currently the only non-boolean argument; check for it first so
             # so the rest of the block can fail through to handling booleans
             if name == "field_specifiers":
                 self.fail('"field_specifiers" support is currently unimplemented', call)
                 continue
 
-            boolean = self.parse_bool(value)
+            boolean = require_bool_literal_argument(self, value, name)
             if boolean is None:
-                self.fail(f'"{name}" argument must be a True or False literal', call)
                 continue
 
             if name == "eq_default":
diff --git a/mypy/semanal_shared.py b/mypy/semanal_shared.py
index dd069fbaec98..03efbe6ca1b8 100644
--- a/mypy/semanal_shared.py
+++ b/mypy/semanal_shared.py
@@ -3,13 +3,13 @@
 from __future__ import annotations
 
 from abc import abstractmethod
-from typing import Callable
-from typing_extensions import Final, Protocol
+from typing import Callable, overload
+from typing_extensions import Final, Literal, Protocol
 
 from mypy_extensions import trait
 
 from mypy import join
-from mypy.errorcodes import ErrorCode
+from mypy.errorcodes import LITERAL_REQ, ErrorCode
 from mypy.nodes import (
     CallExpr,
     ClassDef,
@@ -26,6 +26,7 @@
     SymbolTableNode,
     TypeInfo,
 )
+from mypy.plugin import SemanticAnalyzerPluginInterface
 from mypy.tvar_scope import TypeVarLikeScope
 from mypy.type_visitor import ANY_STRATEGY, BoolTypeQuery
 from mypy.types import (
@@ -420,3 +421,41 @@ def find_dataclass_transform_spec(node: Node | None) -> DataclassTransformSpec |
             return metaclass_type.type.dataclass_transform_spec
 
     return None
+
+
+# Never returns `None` if a default is given
+@overload
+def require_bool_literal_argument(
+    api: SemanticAnalyzerInterface | SemanticAnalyzerPluginInterface,
+    expression: Expression,
+    name: str,
+    default: Literal[True] | Literal[False],
+) -> bool:
+    ...
+
+
+@overload
+def require_bool_literal_argument(
+    api: SemanticAnalyzerInterface | SemanticAnalyzerPluginInterface,
+    expression: Expression,
+    name: str,
+    default: None = None,
+) -> bool | None:
+    ...
+
+
+def require_bool_literal_argument(
+    api: SemanticAnalyzerInterface | SemanticAnalyzerPluginInterface,
+    expression: Expression,
+    name: str,
+    default: bool | None = None,
+) -> bool | None:
+    """Attempt to interpret an expression as a boolean literal, and fail analysis if we can't."""
+    value = api.parse_bool(expression)
+    if value is None:
+        api.fail(
+            f'"{name}" argument must be a True or False literal', expression, code=LITERAL_REQ
+        )
+        return default
+
+    return value
diff --git a/mypy/semanal_typeddict.py b/mypy/semanal_typeddict.py
index 55618318c1e8..acb93edb7d2d 100644
--- a/mypy/semanal_typeddict.py
+++ b/mypy/semanal_typeddict.py
@@ -31,7 +31,11 @@
     TypeInfo,
 )
 from mypy.options import Options
-from mypy.semanal_shared import SemanticAnalyzerInterface, has_placeholder
+from mypy.semanal_shared import (
+    SemanticAnalyzerInterface,
+    has_placeholder,
+    require_bool_literal_argument,
+)
 from mypy.typeanal import check_for_explicit_any, has_any_from_unimported_type
 from mypy.types import (
     TPDICT_NAMES,
@@ -320,10 +324,7 @@ def analyze_typeddict_classdef_fields(
                     self.fail("Right hand side values are not supported in TypedDict", stmt)
         total: bool | None = True
         if "total" in defn.keywords:
-            total = self.api.parse_bool(defn.keywords["total"])
-            if total is None:
-                self.fail('Value of "total" must be True or False', defn)
-                total = True
+            total = require_bool_literal_argument(self.api, defn.keywords["total"], "total", True)
         required_keys = {
             field
             for (field, t) in zip(fields, types)
@@ -436,11 +437,9 @@ def parse_typeddict_args(
             )
         total: bool | None = True
         if len(args) == 3:
-            total = self.api.parse_bool(call.args[2])
+            total = require_bool_literal_argument(self.api, call.args[2], "total")
             if total is None:
-                return self.fail_typeddict_arg(
-                    'TypedDict() "total" argument must be True or False', call
-                )
+                return "", [], [], True, [], False
         dictexpr = args[1]
         tvar_defs = self.api.get_and_bind_all_tvars([t for k, t in dictexpr.items])
         res = self.parse_typeddict_fields_with_types(dictexpr.items, call)
diff --git a/test-data/unit/check-attr.test b/test-data/unit/check-attr.test
index f555f2ea7011..f6ef289e792e 100644
--- a/test-data/unit/check-attr.test
+++ b/test-data/unit/check-attr.test
@@ -151,9 +151,9 @@ class D:
 [case testAttrsNotBooleans]
 import attr
 x = True
-@attr.s(cmp=x)  # E: "cmp" argument must be True or False.
+@attr.s(cmp=x)  # E: "cmp" argument must be a True, False, or None literal
 class A:
-    a = attr.ib(init=x)  # E: "init" argument must be True or False.
+    a = attr.ib(init=x)  # E: "init" argument must be a True or False literal
 [builtins fixtures/bool.pyi]
 
 [case testAttrsInitFalse]
@@ -1866,4 +1866,4 @@ reveal_type(D) # N: Revealed type is "def (a: builtins.int, b: builtins.str) ->
 D(1, "").a = 2 # E: Cannot assign to final attribute "a"
 D(1, "").b = "2" # E: Cannot assign to final attribute "b"
 
-[builtins fixtures/property.pyi]
\ No newline at end of file
+[builtins fixtures/property.pyi]
diff --git a/test-data/unit/check-dataclass-transform.test b/test-data/unit/check-dataclass-transform.test
index 40f3a4cde5fb..bc8fe1ecf58c 100644
--- a/test-data/unit/check-dataclass-transform.test
+++ b/test-data/unit/check-dataclass-transform.test
@@ -83,12 +83,12 @@ class BaseClass:
 class Metaclass(type): ...
 
 BOOL_CONSTANT = True
-@my_dataclass(eq=BOOL_CONSTANT)  # E: "eq" argument must be True or False.
+@my_dataclass(eq=BOOL_CONSTANT)  # E: "eq" argument must be a True or False literal
 class A: ...
-@my_dataclass(order=not False)  # E: "order" argument must be True or False.
+@my_dataclass(order=not False)  # E: "order" argument must be a True or False literal
 class B: ...
-class C(BaseClass, eq=BOOL_CONSTANT): ...  # E: "eq" argument must be True or False
-class D(metaclass=Metaclass, order=not False): ...  # E: "order" argument must be True or False
+class C(BaseClass, eq=BOOL_CONSTANT): ...  # E: "eq" argument must be a True or False literal
+class D(metaclass=Metaclass, order=not False): ...  # E: "order" argument must be a True or False literal
 
 [typing fixtures/typing-full.pyi]
 [builtins fixtures/dataclasses.pyi]
diff --git a/test-data/unit/check-typeddict.test b/test-data/unit/check-typeddict.test
index 1f200d168a55..e3d6188b643b 100644
--- a/test-data/unit/check-typeddict.test
+++ b/test-data/unit/check-typeddict.test
@@ -1084,8 +1084,8 @@ reveal_type(d) \
 
 [case testTypedDictWithInvalidTotalArgument]
 from mypy_extensions import TypedDict
-A = TypedDict('A', {'x': int}, total=0) # E: TypedDict() "total" argument must be True or False
-B = TypedDict('B', {'x': int}, total=bool) # E: TypedDict() "total" argument must be True or False
+A = TypedDict('A', {'x': int}, total=0) # E: "total" argument must be a True or False literal
+B = TypedDict('B', {'x': int}, total=bool) # E: "total" argument must be a True or False literal
 C = TypedDict('C', {'x': int}, x=False) # E: Unexpected keyword argument "x" for "TypedDict"
 D = TypedDict('D', {'x': int}, False) # E: Unexpected arguments to TypedDict()
 [builtins fixtures/dict.pyi]
@@ -1179,12 +1179,12 @@ reveal_type(d) # N: Revealed type is "TypedDict('__main__.D', {'x'?: builtins.in
 
 [case testTypedDictClassWithInvalidTotalArgument]
 from mypy_extensions import TypedDict
-class D(TypedDict, total=1): # E: Value of "total" must be True or False
+class D(TypedDict, total=1): # E: "total" argument must be a True or False literal
     x: int
-class E(TypedDict, total=bool): # E: Value of "total" must be True or False
+class E(TypedDict, total=bool): # E: "total" argument must be a True or False literal
     x: int
-class F(TypedDict, total=xyz): # E: Value of "total" must be True or False \
-                               # E: Name "xyz" is not defined
+class F(TypedDict, total=xyz): # E: Name "xyz" is not defined \
+                               # E: "total" argument must be a True or False literal
     x: int
 [builtins fixtures/dict.pyi]