diff --git a/Lib/test/test_tkinter/test_simpledialog.py b/Lib/test/test_tkinter/test_simpledialog.py
index be0be8d3f546311..81f7676d6e5a2b8 100644
--- a/Lib/test/test_tkinter/test_simpledialog.py
+++ b/Lib/test/test_tkinter/test_simpledialog.py
@@ -448,7 +448,9 @@ def open(self, query, **kw):
     def enter(self, d, value, key='<Return>'):
         d.entry.delete(0, 'end')
         d.entry.insert(0, value)
-        d.event_generate(key)
+        d.entry.focus_set()
+        d.update_idletasks()
+        d.entry.event_generate(key)
         d.update()
 
     # --- Prompt and entry ---
diff --git a/Misc/NEWS.d/next/Library/2026-07-21-14-49-05.gh-issue-154357.YaqVLI.rst b/Misc/NEWS.d/next/Library/2026-07-21-14-49-05.gh-issue-154357.YaqVLI.rst
new file mode 100644
index 000000000000000..b323f2bb2b078f2
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-07-21-14-49-05.gh-issue-154357.YaqVLI.rst
@@ -0,0 +1 @@
+Fix race condition in :mod:`tkinter.simpledialog` tests by explicitly setting focus to entry before generating events.