diff --git a/pandas-stubs/_typing.pyi b/pandas-stubs/_typing.pyi
index 3ad916f76..cb6fa46bb 100644
--- a/pandas-stubs/_typing.pyi
+++ b/pandas-stubs/_typing.pyi
@@ -24,7 +24,10 @@ from pandas.core.generic import NDFrame
 from pandas.core.groupby.grouper import Grouper
 from pandas.core.indexes.base import Index
 from pandas.core.series import Series
-from typing_extensions import TypeAlias
+from typing_extensions import (
+    ParamSpec,
+    TypeAlias,
+)
 
 from pandas._libs.interval import Interval
 from pandas._libs.tslibs import (
@@ -123,6 +126,7 @@ JSONSerializable: TypeAlias = Union[PythonScalar, list, dict]
 Axes: TypeAlias = Union[AnyArrayLike, list, dict, range, tuple]
 Renamer: TypeAlias = Union[Mapping[Any, Label], Callable[[Any], Label]]
 T = TypeVar("T")
+P = ParamSpec("P")
 FuncType: TypeAlias = Callable[..., Any]
 F = TypeVar("F", bound=FuncType)
 HashableT = TypeVar("HashableT", bound=Hashable)
@@ -202,6 +206,27 @@ S1 = TypeVar(
     Interval[Timestamp],
     Interval[Timedelta],
 )
+S2 = TypeVar(
+    "S2",
+    str,
+    bytes,
+    datetime.date,
+    datetime.datetime,
+    datetime.time,
+    datetime.timedelta,
+    bool,
+    int,
+    float,
+    complex,
+    Timestamp,
+    Timedelta,
+    np.datetime64,
+    Period,
+    Interval[int],
+    Interval[float],
+    Interval[Timestamp],
+    Interval[Timedelta],
+)
 T1 = TypeVar(
     "T1", str, int, np.int64, np.uint64, np.float64, float, np.dtype[np.generic]
 )
@@ -285,6 +310,44 @@ GroupByObjectNonScalar: TypeAlias = Union[
     list[Grouper],
 ]
 GroupByObject: TypeAlias = Union[Scalar, GroupByObjectNonScalar]
+GroupByFuncStrs: TypeAlias = Literal[
+    # Reduction/aggregation functions
+    "all",
+    "any",
+    "corrwith",
+    "count",
+    "first",
+    "idxmax",
+    "idxmin",
+    "last",
+    "max",
+    "mean",
+    "median",
+    "min",
+    "nunique",
+    "prod",
+    "quantile",
+    "sem",
+    "size",
+    "skew",
+    "std",
+    "sum",
+    "var",
+    # Transformation functions
+    "bfill",
+    "cumcount",
+    "cummax",
+    "cummin",
+    "cumprod",
+    "cumsum",
+    "diff",
+    "ffill",
+    "fillna",
+    "ngroup",
+    "pct_change",
+    "rank",
+    "shift",
+]
 
 StataDateFormat: TypeAlias = Literal[
     "tc",
diff --git a/pandas-stubs/core/groupby/generic.pyi b/pandas-stubs/core/groupby/generic.pyi
index c4a56f8b0..47b8ea3e5 100644
--- a/pandas-stubs/core/groupby/generic.pyi
+++ b/pandas-stubs/core/groupby/generic.pyi
@@ -22,15 +22,21 @@ from pandas.core.groupby.groupby import (  # , get_groupby as get_groupby
 )
 from pandas.core.groupby.grouper import Grouper
 from pandas.core.series import Series
-from typing_extensions import TypeAlias
+from typing_extensions import (
+    Concatenate,
+    TypeAlias,
+)
 
 from pandas._typing import (
     S1,
+    S2,
     AggFuncTypeBase,
     AggFuncTypeFrame,
     AxisType,
+    GroupByFuncStrs,
     Level,
     ListLike,
+    P,
     Scalar,
 )
 
@@ -61,7 +67,17 @@ class SeriesGroupBy(GroupBy, Generic[S1]):
     def agg(self, func: list[AggFuncTypeBase], *args, **kwargs) -> DataFrame: ...
     @overload
     def agg(self, func: AggFuncTypeBase, *args, **kwargs) -> Series: ...
-    def transform(self, func: Callable | str, *args, **kwargs) -> Series: ...
+    @overload
+    def transform(
+        self,
+        func: Callable[Concatenate[Series[S1], P], Series[S2]],
+        *args: P.args,
+        engine: Literal["cython", "numba", None] = ...,
+        engine_kwargs: dict[str, Any] | None = ...,
+        **kwargs: P.kwargs,
+    ) -> Series[S2]: ...
+    @overload
+    def transform(self, func: GroupByFuncStrs, *args, **kwargs) -> Series: ...
     def filter(self, func, dropna: bool = ..., *args, **kwargs): ...
     def nunique(self, dropna: bool = ...) -> Series: ...
     def describe(self, **kwargs) -> DataFrame: ...
diff --git a/tests/test_series.py b/tests/test_series.py
index 12beb716d..c5d06f6d8 100644
--- a/tests/test_series.py
+++ b/tests/test_series.py
@@ -517,6 +517,24 @@ def test_types_groupby_methods() -> None:
     check(assert_type(s.groupby(level=0).unique(), pd.Series), pd.Series)
 
 
+def test_types_groupby_transform() -> None:
+    s: pd.Series[int] = pd.Series([4, 2, 1, 8], index=["a", "b", "a", "b"])
+
+    def transform_func(
+        x: pd.Series[int], pos_arg: bool, kw_arg: str
+    ) -> pd.Series[float]:
+        return x / (2.0 if pos_arg else 1.0)
+
+    check(
+        assert_type(
+            s.groupby(lambda x: x).transform(transform_func, True, kw_arg="foo"),
+            "pd.Series[float]",
+        ),
+        pd.Series,
+        float,
+    )
+
+
 def test_types_groupby_agg() -> None:
     s = pd.Series([4, 2, 1, 8], index=["a", "b", "a", "b"])
     check(assert_type(s.groupby(level=0).agg("sum"), pd.Series), pd.Series)
@@ -641,9 +659,9 @@ def test_types_aggregate() -> None:
 
 
 def test_types_transform() -> None:
-    s = pd.Series([1, 2, 3], index=["col1", "col2", "col3"])
-    check(assert_type(s.transform("abs"), pd.Series), pd.Series)
-    check(assert_type(s.transform(abs), pd.Series), pd.Series)
+    s: pd.Series[int] = pd.Series([1, 2, 3], index=["col1", "col2", "col3"])
+    check(assert_type(s.transform("abs"), "pd.Series[int]"), pd.Series, int)
+    check(assert_type(s.transform(abs), "pd.Series[int]"), pd.Series, int)
     check(assert_type(s.transform(["abs", "sqrt"]), pd.DataFrame), pd.DataFrame)
     check(assert_type(s.transform([abs, np.sqrt]), pd.DataFrame), pd.DataFrame)
     check(