diff --git a/stdlib/@tests/stubtest_allowlists/py314.txt b/stdlib/@tests/stubtest_allowlists/py314.txt
index 161310ad18bb..83fb0a8cc30b 100644
--- a/stdlib/@tests/stubtest_allowlists/py314.txt
+++ b/stdlib/@tests/stubtest_allowlists/py314.txt
@@ -162,7 +162,6 @@ multiprocessing.process.BaseProcess.interrupt
 multiprocessing.synchronize.SemLock.locked
 os.__all__
 os.readinto
-pathlib.Path.copy_into
 pathlib.Path.copytree
 pathlib.Path.delete
 pathlib.Path.info
diff --git a/stdlib/@tests/test_cases/check_pathlib.py b/stdlib/@tests/test_cases/check_pathlib.py
index 9b4d681c9e96..1ff03c9b8c68 100644
--- a/stdlib/@tests/test_cases/check_pathlib.py
+++ b/stdlib/@tests/test_cases/check_pathlib.py
@@ -4,6 +4,10 @@
 from pathlib import Path, PureWindowsPath
 from typing_extensions import assert_type
 
+
+class MyCustomPath(Path): ...
+
+
 if Path("asdf") == Path("asdf"):
     ...
 
@@ -23,8 +27,14 @@
 
 
 if sys.version_info >= (3, 13):
+    pth = MyCustomPath.from_uri("file:///tmp/abc.txt")
+    assert_type(pth, MyCustomPath)
 
-    class MyCustomPath(Path): ...
+if sys.version_info >= (3, 14):
+    my_path = MyCustomPath(".")
+    pth = my_path.copy_into(Path("."))
+    assert_type(pth, Path)
 
-    pth = MyCustomPath.from_uri("file:///tmp/abc.txt")
+    # If the destination is a non-Path, it should default to `Self`.
+    pth = my_path.copy_into(".")
     assert_type(pth, MyCustomPath)
diff --git a/stdlib/pathlib.pyi b/stdlib/pathlib.pyi
index 1e4d97770b7b..7a5b494b70fd 100644
--- a/stdlib/pathlib.pyi
+++ b/stdlib/pathlib.pyi
@@ -15,9 +15,11 @@ from collections.abc import Callable, Generator, Iterator, Sequence
 from io import BufferedRandom, BufferedReader, BufferedWriter, FileIO, TextIOWrapper
 from os import PathLike, stat_result
 from types import GenericAlias, TracebackType
-from typing import IO, Any, BinaryIO, ClassVar, Literal, overload
+from typing import IO, Any, BinaryIO, ClassVar, Literal, TypeVar, overload
 from typing_extensions import Never, Self, deprecated
 
+_T = TypeVar("_T", bound=PurePath)
+
 __all__ = ["PurePath", "PurePosixPath", "PureWindowsPath", "Path", "PosixPath", "WindowsPath"]
 
 if sys.version_info >= (3, 13):
@@ -154,6 +156,10 @@ class Path(PurePath):
     def mkdir(self, mode: int = 0o777, parents: bool = False, exist_ok: bool = False) -> None: ...
 
     if sys.version_info >= (3, 14):
+        @overload
+        def copy_into(self, target_dir: _T, *, follow_symlinks: bool = True, preserve_metadata: bool = False) -> _T: ...  # type: ignore[overload-overlap]
+        @overload
+        def copy_into(self, target_dir: StrPath, *, follow_symlinks: bool = True, preserve_metadata: bool = False) -> Self: ...
         def copy(self, target: StrPath, *, follow_symlinks: bool = True, preserve_metadata: bool = False) -> None: ...
         def copytree(
             self,