diff --git a/stdlib/tkinter/commondialog.pyi b/stdlib/tkinter/commondialog.pyi
index 2891f7fa8..6dba6bd60 100644
--- a/stdlib/tkinter/commondialog.pyi
+++ b/stdlib/tkinter/commondialog.pyi
@@ -11,4 +11,4 @@ class Dialog:
     # sometimes changed to a different type.
     options: Mapping[str, Any]
     def __init__(self, master: Misc | None = None, **options: Any) -> None: ...
-    def show(self, **options: Any): ...
+    def show(self, **options: Any) -> Any: ...
diff --git a/stdlib/tkinter/messagebox.pyi b/stdlib/tkinter/messagebox.pyi
index 902fab62a..8e5a88f92 100644
--- a/stdlib/tkinter/messagebox.pyi
+++ b/stdlib/tkinter/messagebox.pyi
@@ -1,5 +1,6 @@
+from tkinter import Misc
 from tkinter.commondialog import Dialog
-from typing import ClassVar, Final
+from typing import ClassVar, Final, Literal
 
 __all__ = ["showinfo", "showwarning", "showerror", "askquestion", "askokcancel", "askyesno", "askyesnocancel", "askretrycancel"]
 
@@ -23,11 +24,75 @@ NO: Final = "no"
 class Message(Dialog):
     command: ClassVar[str]
 
-def showinfo(title: str | None = None, message: str | None = None, **options) -> str: ...
-def showwarning(title: str | None = None, message: str | None = None, **options) -> str: ...
-def showerror(title: str | None = None, message: str | None = None, **options) -> str: ...
-def askquestion(title: str | None = None, message: str | None = None, **options) -> str: ...
-def askokcancel(title: str | None = None, message: str | None = None, **options) -> bool: ...
-def askyesno(title: str | None = None, message: str | None = None, **options) -> bool: ...
-def askyesnocancel(title: str | None = None, message: str | None = None, **options) -> bool | None: ...
-def askretrycancel(title: str | None = None, message: str | None = None, **options) -> bool: ...
+def showinfo(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["ok"] = ...,
+    parent: Misc = ...,
+) -> str: ...
+def showwarning(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["ok"] = ...,
+    parent: Misc = ...,
+) -> str: ...
+def showerror(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["ok"] = ...,
+    parent: Misc = ...,
+) -> str: ...
+def askquestion(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["yes", "no"] = ...,
+    parent: Misc = ...,
+) -> str: ...
+def askokcancel(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["ok", "cancel"] = ...,
+    parent: Misc = ...,
+) -> bool: ...
+def askyesno(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["yes", "no"] = ...,
+    parent: Misc = ...,
+) -> bool: ...
+def askyesnocancel(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["cancel", "yes", "no"] = ...,
+    parent: Misc = ...,
+) -> bool | None: ...
+def askretrycancel(
+    title: str | None = None,
+    message: str | None = None,
+    *,
+    detail: str = ...,
+    icon: Literal["error", "info", "question", "warning"] = ...,
+    default: Literal["retry", "cancel"] = ...,
+    parent: Misc = ...,
+) -> bool: ...