diff --git a/Lib/test/test_winsound.py b/Lib/test/test_winsound.py
index 27597874a8e..069adc39810 100644
--- a/Lib/test/test_winsound.py
+++ b/Lib/test/test_winsound.py
@@ -158,14 +158,15 @@ class PlaySoundTest(unittest.TestCase):
             )
 
     def test_alias_fallback(self):
-        if _have_soundcard():
+        # In the absense of the ability to tell if a sound was actually
+        # played, this test has two acceptable outcomes: success (no error,
+        # sound was theoretically played; although as issue #19987 shows
+        # a box without a soundcard can "succeed") or RuntimeError.  Any
+        # other error is a failure.
+        try:
             winsound.PlaySound('!"$%&/(#+*', winsound.SND_ALIAS)
-        else:
-            self.assertRaises(
-                RuntimeError,
-                winsound.PlaySound,
-                '!"$%&/(#+*', winsound.SND_ALIAS
-            )
+        except RuntimeError:
+            pass
 
     def test_alias_nofallback(self):
         if _have_soundcard():
diff --git a/Misc/NEWS b/Misc/NEWS
index b0c1e36684c..cacfb7c6b7b 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -160,7 +160,7 @@ Tests
 - Issue #19926: Removed unneeded test_main from test_abstract_numbers.
   Patch by Vajrasky Kok.
 
-- Issue #19595: Re-enabled a long-disabled test in test_winsound.
+- Issue #19595, #19987: Re-enabled a long-disabled test in test_winsound.
 
 - Issue #19588: Fixed tests in test_random that were silently skipped most
   of the time.  Patch by Julian Gindi.