diff --git a/mypy/plugins/common.py b/mypy/plugins/common.py
index 0acf3e3a6369..67796ef15cf3 100644
--- a/mypy/plugins/common.py
+++ b/mypy/plugins/common.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+from mypy.argmap import map_actuals_to_formals
 from mypy.fixup import TypeFixer
 from mypy.nodes import (
     ARG_POS,
@@ -13,6 +14,7 @@
     Expression,
     FuncDef,
     JsonDict,
+    NameExpr,
     Node,
     PassStmt,
     RefExpr,
@@ -22,6 +24,7 @@
 from mypy.plugin import CheckerPluginInterface, ClassDefContext, SemanticAnalyzerPluginInterface
 from mypy.semanal_shared import (
     ALLOW_INCOMPATIBLE_OVERRIDE,
+    parse_bool,
     require_bool_literal_argument,
     set_callable_name,
 )
@@ -29,13 +32,19 @@
     try_getting_str_literals as try_getting_str_literals,
 )
 from mypy.types import (
+    AnyType,
     CallableType,
+    Instance,
+    LiteralType,
+    NoneType,
     Overloaded,
     Type,
+    TypeOfAny,
     TypeType,
     TypeVarType,
     deserialize_type,
     get_proper_type,
+    is_optional,
 )
 from mypy.typevars import fill_typevars
 from mypy.util import get_unique_redefinition_name
@@ -87,6 +96,71 @@ def _get_argument(call: CallExpr, name: str) -> Expression | None:
     return None
 
 
+def find_shallow_matching_overload_item(overload: Overloaded, call: CallExpr) -> CallableType:
+    """Perform limited lookup of a matching overload item.
+
+    Full overload resolution is only supported during type checking, but plugins
+    sometimes need to resolve overloads. This can be used in some such use cases.
+
+    Resolve overloads based on these things only:
+
+    * Match using argument kinds and names
+    * If formal argument has type None, only accept the "None" expression in the callee
+    * If formal argument has type Literal[True] or Literal[False], only accept the
+      relevant bool literal
+
+    Return the first matching overload item, or the last one if nothing matches.
+    """
+    for item in overload.items[:-1]:
+        ok = True
+        mapped = map_actuals_to_formals(
+            call.arg_kinds,
+            call.arg_names,
+            item.arg_kinds,
+            item.arg_names,
+            lambda i: AnyType(TypeOfAny.special_form),
+        )
+
+        # Look for extra actuals
+        matched_actuals = set()
+        for actuals in mapped:
+            matched_actuals.update(actuals)
+        if any(i not in matched_actuals for i in range(len(call.args))):
+            ok = False
+
+        for arg_type, kind, actuals in zip(item.arg_types, item.arg_kinds, mapped):
+            if kind.is_required() and not actuals:
+                # Missing required argument
+                ok = False
+                break
+            elif actuals:
+                args = [call.args[i] for i in actuals]
+                arg_type = get_proper_type(arg_type)
+                arg_none = any(isinstance(arg, NameExpr) and arg.name == "None" for arg in args)
+                if isinstance(arg_type, NoneType):
+                    if not arg_none:
+                        ok = False
+                        break
+                elif (
+                    arg_none
+                    and not is_optional(arg_type)
+                    and not (
+                        isinstance(arg_type, Instance)
+                        and arg_type.type.fullname == "builtins.object"
+                    )
+                    and not isinstance(arg_type, AnyType)
+                ):
+                    ok = False
+                    break
+                elif isinstance(arg_type, LiteralType) and type(arg_type.value) is bool:
+                    if not any(parse_bool(arg) == arg_type.value for arg in args):
+                        ok = False
+                        break
+        if ok:
+            return item
+    return overload.items[-1]
+
+
 def _get_callee_type(call: CallExpr) -> CallableType | None:
     """Return the type of the callee, regardless of its syntatic form."""
 
@@ -103,8 +177,7 @@ def _get_callee_type(call: CallExpr) -> CallableType | None:
     if isinstance(callee_node, (Var, SYMBOL_FUNCBASE_TYPES)) and callee_node.type:
         callee_node_type = get_proper_type(callee_node.type)
         if isinstance(callee_node_type, Overloaded):
-            # We take the last overload.
-            return callee_node_type.items[-1]
+            return find_shallow_matching_overload_item(callee_node_type, call)
         elif isinstance(callee_node_type, CallableType):
             return callee_node_type
 
diff --git a/mypy/plugins/dataclasses.py b/mypy/plugins/dataclasses.py
index e84e1dbb9491..9fa32a108b74 100644
--- a/mypy/plugins/dataclasses.py
+++ b/mypy/plugins/dataclasses.py
@@ -40,6 +40,7 @@
 )
 from mypy.plugin import ClassDefContext, SemanticAnalyzerPluginInterface
 from mypy.plugins.common import (
+    _get_callee_type,
     _get_decorator_bool_argument,
     add_attribute_to_class,
     add_method_to_class,
@@ -48,7 +49,7 @@
 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
+from mypy.typeops import map_type_from_supertype, try_getting_literals_from_type
 from mypy.types import (
     AnyType,
     CallableType,
@@ -517,7 +518,7 @@ def collect_attributes(self) -> list[DataclassAttribute] | None:
 
             is_in_init_param = field_args.get("init")
             if is_in_init_param is None:
-                is_in_init = True
+                is_in_init = self._get_default_init_value_for_field_specifier(stmt.rvalue)
             else:
                 is_in_init = bool(self._api.parse_bool(is_in_init_param))
 
@@ -760,6 +761,30 @@ def _get_bool_arg(self, name: str, default: bool) -> bool:
             return require_bool_literal_argument(self._api, expression, name, default)
         return default
 
+    def _get_default_init_value_for_field_specifier(self, call: Expression) -> bool:
+        """
+        Find a default value for the `init` parameter of the specifier being called. If the
+        specifier's type signature includes an `init` parameter with a type of `Literal[True]` or
+        `Literal[False]`, return the appropriate boolean value from the literal. Otherwise,
+        fall back to the standard default of `True`.
+        """
+        if not isinstance(call, CallExpr):
+            return True
+
+        specifier_type = _get_callee_type(call)
+        if specifier_type is None:
+            return True
+
+        parameter = specifier_type.argument_by_name("init")
+        if parameter is None:
+            return True
+
+        literals = try_getting_literals_from_type(parameter.typ, bool, "builtins.bool")
+        if literals is None or len(literals) != 1:
+            return True
+
+        return literals[0]
+
     def _infer_dataclass_attr_init_type(
         self, sym: SymbolTableNode, name: str, context: Context
     ) -> Type | None:
diff --git a/mypy/semanal.py b/mypy/semanal.py
index 4ee18d5ff4d3..84573790fd68 100644
--- a/mypy/semanal.py
+++ b/mypy/semanal.py
@@ -216,6 +216,7 @@
     calculate_tuple_fallback,
     find_dataclass_transform_spec,
     has_placeholder,
+    parse_bool,
     require_bool_literal_argument,
     set_callable_name as set_callable_name,
 )
@@ -6462,12 +6463,8 @@ def is_initial_mangled_global(self, name: str) -> bool:
         return name == unmangle(name) + "'"
 
     def parse_bool(self, expr: Expression) -> bool | None:
-        if isinstance(expr, NameExpr):
-            if expr.fullname == "builtins.True":
-                return True
-            if expr.fullname == "builtins.False":
-                return False
-        return None
+        # This wrapper is preserved for plugins.
+        return parse_bool(expr)
 
     def parse_str_literal(self, expr: Expression) -> str | None:
         """Attempt to find the string literal value of the given expression. Returns `None` if no
diff --git a/mypy/semanal_shared.py b/mypy/semanal_shared.py
index 03efbe6ca1b8..c86ed828b2b9 100644
--- a/mypy/semanal_shared.py
+++ b/mypy/semanal_shared.py
@@ -18,6 +18,7 @@
     Decorator,
     Expression,
     FuncDef,
+    NameExpr,
     Node,
     OverloadedFuncDef,
     RefExpr,
@@ -451,7 +452,7 @@ def require_bool_literal_argument(
     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)
+    value = parse_bool(expression)
     if value is None:
         api.fail(
             f'"{name}" argument must be a True or False literal', expression, code=LITERAL_REQ
@@ -459,3 +460,12 @@ def require_bool_literal_argument(
         return default
 
     return value
+
+
+def parse_bool(expr: Expression) -> bool | None:
+    if isinstance(expr, NameExpr):
+        if expr.fullname == "builtins.True":
+            return True
+        if expr.fullname == "builtins.False":
+            return False
+    return None
diff --git a/mypy/test/testtypes.py b/mypy/test/testtypes.py
index ee0256e2057a..6fe65675554b 100644
--- a/mypy/test/testtypes.py
+++ b/mypy/test/testtypes.py
@@ -7,7 +7,21 @@
 from mypy.indirection import TypeIndirectionVisitor
 from mypy.join import join_simple, join_types
 from mypy.meet import meet_types, narrow_declared_type
-from mypy.nodes import ARG_OPT, ARG_POS, ARG_STAR, ARG_STAR2, CONTRAVARIANT, COVARIANT, INVARIANT
+from mypy.nodes import (
+    ARG_NAMED,
+    ARG_OPT,
+    ARG_POS,
+    ARG_STAR,
+    ARG_STAR2,
+    CONTRAVARIANT,
+    COVARIANT,
+    INVARIANT,
+    ArgKind,
+    CallExpr,
+    Expression,
+    NameExpr,
+)
+from mypy.plugins.common import find_shallow_matching_overload_item
 from mypy.state import state
 from mypy.subtypes import is_more_precise, is_proper_subtype, is_same_type, is_subtype
 from mypy.test.helpers import Suite, assert_equal, assert_type, skip
@@ -1287,3 +1301,135 @@ def assert_union_result(self, t: ProperType, expected: list[Type]) -> None:
         t2 = remove_instance_last_known_values(t)
         assert type(t2) is UnionType
         assert t2.items == expected
+
+
+class ShallowOverloadMatchingSuite(Suite):
+    def setUp(self) -> None:
+        self.fx = TypeFixture()
+
+    def test_simple(self) -> None:
+        fx = self.fx
+        ov = self.make_overload([[("x", fx.anyt, ARG_NAMED)], [("y", fx.anyt, ARG_NAMED)]])
+        # Match first only
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "x")), 0)
+        # Match second only
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "y")), 1)
+        # No match -- invalid keyword arg name
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "z")), 1)
+        # No match -- missing arg
+        self.assert_find_shallow_matching_overload_item(ov, make_call(), 1)
+        # No match -- extra arg
+        self.assert_find_shallow_matching_overload_item(
+            ov, make_call(("foo", "x"), ("foo", "z")), 1
+        )
+
+    def test_match_using_types(self) -> None:
+        fx = self.fx
+        ov = self.make_overload(
+            [
+                [("x", fx.nonet, ARG_POS)],
+                [("x", fx.lit_false, ARG_POS)],
+                [("x", fx.lit_true, ARG_POS)],
+                [("x", fx.anyt, ARG_POS)],
+            ]
+        )
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("builtins.False", None)), 1)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("builtins.True", None)), 2)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", None)), 3)
+
+    def test_none_special_cases(self) -> None:
+        fx = self.fx
+        ov = self.make_overload(
+            [[("x", fx.callable(fx.nonet), ARG_POS)], [("x", fx.nonet, ARG_POS)]]
+        )
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 1)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("func", None)), 0)
+        ov = self.make_overload([[("x", fx.str_type, ARG_POS)], [("x", fx.nonet, ARG_POS)]])
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 1)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("func", None)), 0)
+        ov = self.make_overload(
+            [[("x", UnionType([fx.str_type, fx.a]), ARG_POS)], [("x", fx.nonet, ARG_POS)]]
+        )
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 1)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("func", None)), 0)
+        ov = self.make_overload([[("x", fx.o, ARG_POS)], [("x", fx.nonet, ARG_POS)]])
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("func", None)), 0)
+        ov = self.make_overload(
+            [[("x", UnionType([fx.str_type, fx.nonet]), ARG_POS)], [("x", fx.nonet, ARG_POS)]]
+        )
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("func", None)), 0)
+        ov = self.make_overload([[("x", fx.anyt, ARG_POS)], [("x", fx.nonet, ARG_POS)]])
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", None)), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("func", None)), 0)
+
+    def test_optional_arg(self) -> None:
+        fx = self.fx
+        ov = self.make_overload(
+            [[("x", fx.anyt, ARG_NAMED)], [("y", fx.anyt, ARG_OPT)], [("z", fx.anyt, ARG_NAMED)]]
+        )
+        self.assert_find_shallow_matching_overload_item(ov, make_call(), 1)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "x")), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "y")), 1)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "z")), 2)
+
+    def test_two_args(self) -> None:
+        fx = self.fx
+        ov = self.make_overload(
+            [
+                [("x", fx.nonet, ARG_OPT), ("y", fx.anyt, ARG_OPT)],
+                [("x", fx.anyt, ARG_OPT), ("y", fx.anyt, ARG_OPT)],
+            ]
+        )
+        self.assert_find_shallow_matching_overload_item(ov, make_call(), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("None", "x")), 0)
+        self.assert_find_shallow_matching_overload_item(ov, make_call(("foo", "x")), 1)
+        self.assert_find_shallow_matching_overload_item(
+            ov, make_call(("foo", "y"), ("None", "x")), 0
+        )
+        self.assert_find_shallow_matching_overload_item(
+            ov, make_call(("foo", "y"), ("bar", "x")), 1
+        )
+
+    def assert_find_shallow_matching_overload_item(
+        self, ov: Overloaded, call: CallExpr, expected_index: int
+    ) -> None:
+        c = find_shallow_matching_overload_item(ov, call)
+        assert c in ov.items
+        assert ov.items.index(c) == expected_index
+
+    def make_overload(self, items: list[list[tuple[str, Type, ArgKind]]]) -> Overloaded:
+        result = []
+        for item in items:
+            arg_types = []
+            arg_names = []
+            arg_kinds = []
+            for name, typ, kind in item:
+                arg_names.append(name)
+                arg_types.append(typ)
+                arg_kinds.append(kind)
+            result.append(
+                CallableType(
+                    arg_types, arg_kinds, arg_names, ret_type=NoneType(), fallback=self.fx.o
+                )
+            )
+        return Overloaded(result)
+
+
+def make_call(*items: tuple[str, str | None]) -> CallExpr:
+    args: list[Expression] = []
+    arg_names = []
+    arg_kinds = []
+    for arg, name in items:
+        shortname = arg.split(".")[-1]
+        n = NameExpr(shortname)
+        n.fullname = arg
+        args.append(n)
+        arg_names.append(name)
+        if name:
+            arg_kinds.append(ARG_NAMED)
+        else:
+            arg_kinds.append(ARG_POS)
+    return CallExpr(NameExpr("f"), args, arg_kinds, arg_names)
diff --git a/mypy/test/typefixture.py b/mypy/test/typefixture.py
index d12e7abab0e2..1013b87c213f 100644
--- a/mypy/test/typefixture.py
+++ b/mypy/test/typefixture.py
@@ -136,6 +136,7 @@ def make_type_var(
         self.type_type = Instance(self.type_typei, [])  # type
         self.function = Instance(self.functioni, [])  # function TODO
         self.str_type = Instance(self.str_type_info, [])
+        self.bool_type = Instance(self.bool_type_info, [])
         self.a = Instance(self.ai, [])  # A
         self.b = Instance(self.bi, [])  # B
         self.c = Instance(self.ci, [])  # C
@@ -197,6 +198,9 @@ def make_type_var(
         self.lit_str2_inst = Instance(self.str_type_info, [], last_known_value=self.lit_str2)
         self.lit_str3_inst = Instance(self.str_type_info, [], last_known_value=self.lit_str3)
 
+        self.lit_false = LiteralType(False, self.bool_type)
+        self.lit_true = LiteralType(True, self.bool_type)
+
         self.type_a = TypeType.make_normalized(self.a)
         self.type_b = TypeType.make_normalized(self.b)
         self.type_c = TypeType.make_normalized(self.c)
diff --git a/test-data/unit/check-dataclass-transform.test b/test-data/unit/check-dataclass-transform.test
index 0b696d36b9bd..be6b46d70846 100644
--- a/test-data/unit/check-dataclass-transform.test
+++ b/test-data/unit/check-dataclass-transform.test
@@ -328,6 +328,38 @@ Foo(a=1, b='bye')
 [typing fixtures/typing-full.pyi]
 [builtins fixtures/dataclasses.pyi]
 
+[case testDataclassTransformFieldSpecifierImplicitInit]
+# flags: --python-version 3.11
+from typing import dataclass_transform, Literal, overload
+
+def init(*, init: Literal[True] = True): ...
+def no_init(*, init: Literal[False] = False): ...
+
+@overload
+def field_overload(*, custom: None, init: Literal[True] = True): ...
+@overload
+def field_overload(*, custom: str, init: Literal[False] = False): ...
+def field_overload(*, custom, init): ...
+
+@dataclass_transform(field_specifiers=(init, no_init, field_overload))
+def my_dataclass(cls): return cls
+
+@my_dataclass
+class Foo:
+    a: int = init()
+    b: int = field_overload(custom=None)
+
+    bad1: int = no_init()
+    bad2: int = field_overload(custom="bad2")
+
+reveal_type(Foo)  # N: Revealed type is "def (a: builtins.int, b: builtins.int) -> __main__.Foo"
+Foo(a=1, b=2)
+Foo(a=1, b=2, bad1=0)  # E: Unexpected keyword argument "bad1" for "Foo"
+Foo(a=1, b=2, bad2=0)  # E: Unexpected keyword argument "bad2" for "Foo"
+
+[typing fixtures/typing-full.pyi]
+[builtins fixtures/dataclasses.pyi]
+
 [case testDataclassTransformOverloadsDecoratorOnOverload]
 # flags: --python-version 3.11
 from typing import dataclass_transform, overload, Any, Callable, Type, Literal