From f4a9a5383f0a1a6bd988dc7fcc29e20a8d7781e6 Mon Sep 17 00:00:00 2001
From: Hrithik Saini <49943287+hrithiksaini99@users.noreply.github.com>
Date: Tue, 3 Nov 2026 10:35:14 +0530
Subject: [PATCH] [tkinter] Fix return types in tkinter.filedialog

Update return types of asksaveasfilename, askopenfilename, and askdirectory
to str | tuple[()] to accommodate empty tuples returned on cancellation.

Closes: #16637
---
 stdlib/@tests/test_cases/check_tkinter.py | 7 +++++++
 stdlib/tkinter/filedialog.pyi             | 6 +++---
 2 files changed, 10 insertions(+), 3 deletions(-)

diff --git a/stdlib/@tests/test_cases/check_tkinter.py b/stdlib/@tests/test_cases/check_tkinter.py
index 62ba0d11f045..a8814299c9ce 100644
--- a/stdlib/@tests/test_cases/check_tkinter.py
+++ b/stdlib/@tests/test_cases/check_tkinter.py
@@ -2,8 +2,10 @@
 
 import sys
 import tkinter
+import tkinter.filedialog
 import traceback
 import types
+from typing import Literal
 from typing_extensions import assert_type
 
 
@@ -71,3 +73,8 @@ def foo(x: int, y: str) -> None:
         t.count("1.0", "2.3", "indices", "lines", "chars", "ypixels", return_ints=True), tuple[int, ...]
     )  # (15, 1, 15, 19)
     assert_type(t.count("2.3", "2.3", "indices", "lines", "chars", "ypixels", return_ints=True), tuple[int, ...])  # (0, 0, 0, 0)
+
+assert_type(tkinter.filedialog.askopenfilename(), str | tuple[()])
+assert_type(tkinter.filedialog.asksaveasfilename(), str | tuple[()])
+assert_type(tkinter.filedialog.askdirectory(), str | tuple[()])
+assert_type(tkinter.filedialog.askopenfilenames(), Literal[""] | tuple[str, ...])
diff --git a/stdlib/tkinter/filedialog.pyi b/stdlib/tkinter/filedialog.pyi
index ba69e90aa2da..1c46112e0fa6 100644
--- a/stdlib/tkinter/filedialog.pyi
+++ b/stdlib/tkinter/filedialog.pyi
@@ -86,7 +86,7 @@ def asksaveasfilename(
     parent: Misc | None = None,
     title: str | None = None,
     typevariable: StringVar | str | None = None,
-) -> str: ...  # can be empty string
+) -> str | tuple[()]: ...  # can be empty string or empty tuple
 def askopenfilename(
     *,
     defaultextension: str | None = "",
@@ -96,7 +96,7 @@ def askopenfilename(
     parent: Misc | None = None,
     title: str | None = None,
     typevariable: StringVar | str | None = None,
-) -> str: ...  # can be empty string
+) -> str | tuple[()]: ...  # can be empty string or empty tuple
 def askopenfilenames(
     *,
     defaultextension: str | None = "",
@@ -113,7 +113,7 @@ def askdirectory(
     mustexist: bool | None = False,
     parent: Misc | None = None,
     title: str | None = None,
-) -> str: ...  # can be empty string
+) -> str | tuple[()]: ...  # can be empty string or empty tuple
 
 # TODO: If someone actually uses these, overload to have the actual return type of open(..., mode)
 def asksaveasfile(